The Best Things to See and Do on a Chicago Trip

This one is all about Chi-town! The windy city has deep historical roots in American history and it’s all over the architecture and personality of this iconic metropolis. We took a quick weekend trip to  Chicago and visited two other states and a national park while on this trip!

You know we can’t take a trip without visiting a national park and getting in some hiking! It was really cool to be sitting along the lake in Indiana Dunes National Park and see Chicago building far across the water. This ide excursion is a must-do on your Chicago weekend trip too if you can make the time for it!

In episode we tell you how to see and do the most in Chicago with just two days. This was all of our first times in the city so these are first time in Chicago things to do recommendations that we did and loved.

Our Chicago travel guide:

  • Architecture boat tour in Chicago – a MUST DO
  • Millennium Park and “the bean”
  • The Chicago riverfront walk
  • Navy Pier
  • John Hancock 96th Floor Signature Lounge
  • Brittanie and Jamal’s first White Claw
  • Road trip to Indiana Dunes National Park
  • Wrigley Field
  • Urkle house from Family matters 

Where to eat in Chicago:

  • Lou Malnati’s pizza
  • Nando’s
  • Chicago dog
  • Italian beef from Portillos 
  • High tea and rooftop bar at London House 

Chicago travel tips:

  • Renting a car
  • A walkable city
  • Chicago’s own rideshare service – vida 
  • Airbnb vs. hotel tips

We’ve created a FREE downloadable 2 day Chicago Guide

Chicago Trip – Episode Transcript

2 (54s):
Hello fellow travelers. Welcome to this weeks episode of the Travel Squad podcast. Today, we’re taking you to the windy city, Chicago, Illinois, for a quick weekend getaway.

1 (1m 5s):
This episode, we are going to talk about exploring downtown Chicago and crossing the state line to explore another national park, Indiana dunes national park, which is a long, the Southern shores of lake Michigan.

3 (1m 17s):
And guys, did you catch us going live on Instagram at Travel Squad Podcast? When we crossed the state lines of Indiana into Michigan? Cause we took you there with us and Brittany. So sneakily as the copilot in the car got me and Kim sleeping in the back seat and yes, she live streamed that for you.

4 (1m 41s):
I absolutely fell in love with Chicago. I love the city. I love the skyline, the energy, the rooftop bars are amazing. There’s so many rooftop bars, rooftop. Our culture is alive and well in Chicago. I just really liked how you’re along the river. There’s people just sitting there eating and drinking and just lounging and just enjoying life. And you know, when we went, the weather was pretty good too. Chicago is known for having some brutal winners, but it was not quite that cold yet. We had some moments where it was windy and a little chili, and we had our jackets and we were bundled up and we even had a period of rain on us at one point. But then we had other times where it was sunny and it was hot winter coats off. It was pretty perfect. I

3 (2m 20s):
Felt like the men were really good looking too.

4 (2m 22s):
Oh my God, there were hot guys everywhere. I was like, I’m moving to Chicago.

3 (2m 27s):
I moved to Chicago and I thought to myself with all these hot men around it’s because my husband is here. I

4 (2m 33s):
Was constantly wiping drool away from my mouth. So Hey, any guys out there in Chicago hit me up lush, DS, Instagram. Okay. Enough about that. So, Brittany, what did we do on this trip? What did you have planned for us?

1 (2m 48s):
I had so much planned for us. I had actually asked for recommendations. Thank you so much Marsal for giving me a ton of recommendations to do in the city. I know you live there and we fell in love with it. Just like you did. We were focused on rooftop bars, exploring downtown and really focusing on the architecture of the city. So that was the, one of the main highlights that we definitely wanted to do

3 (3m 9s):
And try all the food like the pizza, the Philly, cheese steak, and all that. Good. Not

4 (3m 13s):
Exactly Philly cheese, steak, hot

3 (3m 16s):

4 (3m 17s):
Be in Philadelphia,

3 (3m 19s):
Long city.

2 (3m 20s):
It’s like the Philly cheese steak. What is it called? Kim

4 (3m 23s):
In Italian beef, which we’ll talk about in a minute, but we have opinions about that

2 (3m 28s):
Sound scrumptious.

1 (3m 29s):
We’re going to walk you through our days. We landed really late Friday night. It was pretty much Saturday morning. Wasn’t

4 (3m 36s):
About one

1 (3m 36s):
Ish. Yeah. So truly Saturday morning. So we’re gonna walk you through our Saturday and Sunday, We spent a quick weekend in the city. So first we actually rented an Airbnb and we rented the Airbnb in Pilsen, which is a little bit outside and east of downtown. And we rented it there because the price point was right. Downtown Chicago is very expensive and there was nowhere to park a car and we wanted to have a space to park the car because we were planning on crossing the state line. So we found a cute little place in Pilsen that we stayed at. It was two bedroom, two bathroom, perfect for us all getting ready.

3 (4m 11s):
It was the top floor of a four story townhouse. And it gave you the most perfect view of the city at night.

2 (4m 17s):
I loved this Airbnb and Pilsen. It was actually really cool. I think the building itself reminded me of the homes that you would see in New York kind of in Brooklyn. Yeah. It kind of had that vibe to it. And I really liked it. Like Zana said, we were on the fourth story and it just gave amazing views of the Chicago skyline unparalleled. It was actually so amazing to see.

4 (4m 39s):
I had these really tall ceilings too. It definitely had a brownstone kind of vibe

2 (4m 44s):
The school as it was. We didn’t spend a lot of time in there though. Why? Because we were out hitting the pavement, exploring the city,

3 (4m 50s):
Getting that Italian beef.

2 (4m 54s):
So as Brittanie mentioned, we arrived pretty late around 1:00 AM in the morning. So we caught a Lyft. First thing from the airport to our Airbnb went to bed right away, had to wake up early because the next morning to get started, we had the architectural river boat tour, which was amazing by the way. But before we got to downtown to get on the boat, we had a little mishap at

4 (5m 18s):
Mishap or freak out.

2 (5m 21s):
I would call it a mishap. But nonetheless, Brittany found this one cafe called step-down cafe that we decided, okay, we’re going to go there, get breakfast, get some coffee before we caught our Lyft to downtown to catch the boat. And then what happened?

3 (5m 35s):
You like literally have to step down to get into the cafe, which was super cute. But then once you were inside, not so super

2 (5m 41s):
Curious, the name stepped down.

1 (5m 43s):
I hope the cafe was however their service wasn’t that great. I think it would be fine if you were able to sit down there, but we were in a rush and we had to get out the door. And so we waited over 15 minutes to get our food and coffee.

2 (5m 58s):
You’d be generous with that time as well. Over 15 minutes,

3 (6m 2s):
Listeners should know there was no one in line ahead of us. All I did was get a coffee. Kim got a coffee,

4 (6m 7s):
Vanilla latte, and it was probably one of the worst ones I’ve ever had.

1 (6m 11s):
Well, on the other hand, I got an athlete, the mocha, and it was absolutely delicious.

2 (6m 17s):
The mocha Brittanie,

1 (6m 18s):
It was cinnamon sugar spices, coffee and mill

3 (6m 22s):
Sounds good, but no Italian beef in your mouth. I think I’m done with the jokes about Italian beef. Sorry.

2 (6m 29s):
Are you really, I don’t think she is. Anna loves the Italian beef, but know for all that we’re talking about about step-down cafe. It had a really cool local neighborhood coffee bar vibe. No doubt about that. I just think we were on a one-off that day. You know, Kim’s latte. Wasn’t very good. As she mentioned, Brittany’s

1 (6m 50s):
Was spectacular.

2 (6m 51s):
It was spectacular. I would go back Brittanie and I, for breakfast, we ordered their version of egg McMuffins, if you will. And they were actually really good. The problem was it took so long for them to make it with nobody in front of us in line. And we were in that time crunch to catch the boat at 10:00 AM. And it was just taking a little bit too long for comfort for my liking. We were in a rush to get there and they were taking

1 (7m 14s):
So in a rush because Xena and Kim have a whole year ago. They have a hard time getting ready at the right time. Like I am full on mom.

4 (7m 23s):
Here’s the reason why we’re always running just a couple of minutes behind. So Jamal wakes up at the crack of Dawn goes in and out of the shower and gives you the bathroom. Meanwhile Zaina and I wake up pretty much at the same time and we have to share the bathroom and coordinate. And that adds on another two minutes,

1 (7m 41s):
Not another two minutes,

2 (7m 43s):
Water shower together.

3 (7m 45s):
you guys get to shower together. You can take a dump while Brittany’s in the shower. Like all that can go on.

1 (7m 54s):
Can you guys, can you guys, you shared a tent in Machu Picchu on the Inca trail. You share toothbrushes and

4 (8m 1s):
Poop with each other

2 (8m 3s):
Moms just being mom over there

3 (8m 6s):
Because Jamal’s a dude, you know, and it’s to be expected.

2 (8m 11s):
Anyway. Nonetheless, Brittany wants to give a hard time to Kim and Zana for taking a little while to get out the door. Granted, we did have a time and they were delayed on that, but nonetheless,

3 (8m 20s):
So anyways, the cafe, we leave the house at nine 10, we get to the cafe at like nine 13. And we finally leave the cafe at like 9 45 with no one ahead of us.

1 (8m 31s):
Yes. And we have to make it to our 10:00 AM architectural boat tour. We get to the pier and we start running out and we’re like, where is the boat? And the guy was like, they’re already boarding. So we ran down and hopped on the architectural. We

4 (8m 45s):
Had like another five minutes to spare to,

2 (8m 47s):
They did not take off directly at 10 as advertised, which is good for people running a little bit behind. But if they were punctual, it would have cutting them to Tadbik close for us. But we made it on time.

3 (8m 58s):
Jamal was freaking out in the car. In fact, I could already see the beads of sweat for him on his forehead, in the car.

2 (9m 4s):
Our driver was so nice, but you know, sometimes there’s a couple of yellow lights where you can definitely go through them. I don’t want to condone unsafe driving, but nonetheless, she could have definitely made a few of those yellows and she heard we were in a time crunch and she just wanted to slow down for them every

4 (9m 19s):
Single time live the restaurant land.

2 (9m 22s):
Yes, she did. Absolutely. Like I said, great Lyft driver got us there on time to where we

3 (9m 26s):
Could find the Italian beef.

4 (9m 30s):
So that was Jamal’s first freak out of the trip. Brittanie and already had hers, but she’ll have many more

1 (9m 35s):
Based on my two children sitting across from me. Right.

4 (9m 41s):
Okay. So,

1 (9m 42s):
So the Architecture boat tour, just to give you guys a little bit more information on it, I booked it on shoreline sightseeing tours and it was $42 for a 75 minute architectural boat tour. There was two locations. We selected the Michigan avenue pier, but you can also book to leave from the Navy Pier as well. And it is a little bit more to book this tour on the weekend then during the week, but it was really cool and worth it because Wednesdays and Saturdays are the bridge raising days in the fall and spring on the river. So it was actually really cool to see.

4 (10m 16s):
It was very, very cool, not only just the bridge raising, but the tour in general, even if it’s not bridge racing season, the skyline and all the buildings are beautiful. The river is beautiful. There’s so much history in every single building and the tour guide that’s on the mic throughout the tour is so knowledgeable and loves to answer your questions. And it’s just amazing. One of her stories was about the fire. I think it was 1872,

2 (10m 44s):
Nonetheless Chicago fire, the great

4 (10m 46s):
Chicago fire. But anyway, she just gave a history lesson on how that happened or why it happened and how it shaped and formed the downtown Chicago skyline today. And it was really, really cool to see how hundreds of years ago affects what we’re in right now. Yeah.

3 (10m 59s):
In fact, they have no idea how it started. So they created a story that Missy, the cow went crazy, knocked over a lantern and then that started a fire and then burned the city down.

2 (11m 12s):
But that wasn’t what happened.

4 (11m 13s):
The cow was framed.

2 (11m 15s):
It was framed. What really happened? They

3 (11m 17s):
Don’t know

4 (11m 17s):
Zayna knows her

2 (11m 18s):
Shit And listens to a few things on the tours. I’ll give you that selective hearing, I guess,

3 (11m 25s):
You know what? It was fascinating. I can’t tell you how many times I looked over at Jamal and I said, this is so fascinating.

2 (11m 31s):
The river tour was my favorite thing that we did in Chicago, hands down, no dispute about it for me. And I think what I liked most about it was touching on what Kim was saying. It did give you a sense of Chicago’s history through the buildings. Whereas the buildings are the focus. It still gave you a great general history of the whole city itself.

1 (11m 50s):
The few things I want to say about this boat tour one is to dress appropriately for the riverboat to work. We brought a sweater and it was cold on the water. I think all of the ladies were a little bit cold while we were on the boat. Secondly, when Chicago was first building buildings next to the river, it was a lot of industrial buildings. And so Nova and wanted to live in that area because the river was so dirty. And so there were riverfront properties that were not being sold and utilize. And now because they’ve cleaned the river up, everyone wants to live and be near the river. So that was really interesting to learn about. And to hear the last little piece I want to insert was there was a really cool Y looking building, you look at it and you think, how is this even possible for this building to be held up by this Y shaped structure?

1 (12m 36s):
And it actually had a lot to do with when building the building, The Chicago trains or Amtrak were underground. And so they could only build up and over. So they had to be very creative in their architectural structures in order to build properties. And high-rises along the riverfront.

4 (12m 54s):
I think what was really cool about the tour, like Jamal was saying what the history is that the tour guide, she describes the periods of the building. So she would say this one was in the depression. So there was no decoration to it. It’s just a plain black steel building. The next one, she would say this one was during prohibition. So they made it look like a champagne bottle with gold. And it was the guys that designed it who were against prohibition. And then there were some where it was like, this was during the period where this building was made to be their post office. And it was like a whole block long. And then now this building’s used for this and this building was in a movie and so many good factoids.

1 (13m 29s):
Yeah. There were so many interesting buildings too. I love the two towers that look like the corn on the cob.

3 (13m 33s):
So question for you guys, what was your favorite building and why?

4 (13m 37s):
I have so many, but I will go first. Cause I’m so excited about this. My favorite building was the one that from the side of it had all these like blocks sticking out of it. And it was meant to look like the aerial view of the Chicago freeway. So it looked like big, long semi-trucks and cars, but they were just blocks on the side of the building was super cool.

2 (13m 56s):
I remember her talking about that building where the balconies looked like freeway traffic. Yeah.

3 (14m 2s):
Mine was the building that Ferris Bueller’s day off dad from that movie was he worked in, he worked in that building. And the reason why I liked it is because the building is designed to look like water. It’s like you’re looking into water and seeing the city reflected. And the really cool thing that the tour guide was explaining is this building will always remain relevant. If you took a picture of that building in 1992, it’s going to look a lot different than the picture that I would have taken today in 2019, because the reflection is different based on what’s going on behind the city, even though the building itself will never change

2 (14m 39s):
Well, not behind the city, what’s in front of the building to reflect onto it. That’s what you mean, right?

3 (14m 44s):
Yes. That

4 (14m 45s):
Was a pretty well,

1 (14m 46s):
Yeah. I actually took a picture of the reflection after she said

2 (14m 50s):
That my favorite one was the Trump tower. That was right in front. I’m just kidding. My actual favorite building. I forgot what she said. The name of the architect was, but it was that female architect and it’s one of the new ones that they’re building. And it was just really interesting to see, she was talking about how they had to create openings for wind tunnels on the top towers of the building, because it was so tall and thin that with all the wind that comes off of the lake, there would be a lot of suede. So to counteract that they have to put holes in the building. And I thought that was just really unique engineering. Not that I’m an engineer to know, but is to even think about those things and have to do it. That was a cool building.

1 (15m 27s):
My favorite building might’ve been the same as yours. Cause it was also designed by that female w represent

3 (15m 33s):
Yeah, she,

4 (15m 34s):
She is the female architect that has the tallest building in Chicago

1 (15m 40s):
And her building’s actually named Aqua and the building is so tall and there are blue portions of it and it is made to look like water cascading down a waterfall.

4 (15m 51s):
And it was really pretty. She had two buildings up there and I remember one other thing besides the wind tunnels, was it, some rooms were just filled with water so that as the wind blows, the water would splash around in there instead of the buildings, swaying engineering, Marvel,

2 (16m 5s):
I know crazy stuff. So after the amazing boat tour, we decided let’s walk around the city a little bit. Let’s explore. And one thing that we wanted to do was try Lou Malnati S pizza, which was recommended to us by several people that we know from Chicago or used to live in Chicago as one of the most iconic Chicago style pizzas. So we made our way over there. And this is where Kim had her freak out on this trip.

4 (16m 31s):
I wouldn’t call it a

2 (16m 31s):
Rare occasion, but Kim had her freak out on this trip.

4 (16m 35s):
We got there at the perfect time. I think it was like 11, 11 30 and no line got right in. But when we left, there was an hour and 45 minute wait.

2 (16m 43s):
Yeah. When I had walked out the door, cause you ladies were still in the restroom. I heard the hostess tell somebody right now, we’re looking at an hour and 45 minutes. Woo.

3 (16m 52s):
That’s crazy because that’s just to sit down. And even when we sat down, they told us that it was going to take 30 to 45 minutes just for the pizza to get out once we ordered it. So imagine waiting an hour and 45 minutes and then on top of that, another 45 minutes just to get your pizza.

2 (17m 6s):
So we got there at the perfect time. So pro-tip, if you’re going to go there for lunch, do it early, have an early lunch. Otherwise you’re going to wait a lot of time and there are multiple locations. It is a local chain. So we were at one specific location, close to downtown. There may be others closer to the area that you’re in. So there’s not one specific one, but the one we went to had a really, really long line by the time we left.

1 (17m 29s):
So Kim walk us through your freak out.

4 (17m 32s):
Okay. So I don’t like mushrooms, but the Lou pizza that looked really, really good had mushrooms. And so I was debating. Do I go out and get a personal size pizza? How big is the personal size pizza? I don’t want to eat a lot of pizza. So I’m going back and forth in my head trying to figure this out. And Zayna is like, I don’t know what she said, but was something along the lines of,

3 (17m 51s):
Hey Kim, I don’t know if you heard our waiter, but just a friendly reminder. The place is filling up fast. And he said, it takes about 30, 45 minutes to get the pizza and all these people are coming in and putting in their orders. So we may have to wait a little bit longer, you know, Just a courtesy, courtesy reminder, friendly reminder. I don’t know if Kim noticed that he said that the first time and Kim was deeply engulfed in her thoughts

1 (18m 17s):
And Xena, as you describe it right now, you did it so much more politely than you did in person.

4 (18m 23s):
I was about to just be like, fuck this. I don’t want pizza anymore. Fucking outta here

1 (18m 27s):
Hurt and much shorter in person.

2 (18m 29s):
I don’t think he said it in a mean way. When

1 (18m 32s):
You said it in a mean way,

4 (18m 33s):
It was a matter of fact, kind

1 (18m 35s):
Of like it was more short and Curt,

3 (18m 37s):
You know, I think I’m so nice. And then everyone’s,

4 (18m 40s):
But you know, who saved the day

2 (18m 42s):
I saved the day,

4 (18m 43s):
Jamal is so polite and he does this all the time, but he said, the guy could only do half and half no mushrooms, mushrooms. The girls were not budging on the mushrooms. And so Jamal said, I will not eat mushrooms, even though he likes mushrooms and I reluctantly, but happily agreed to go in on this pizza with them.

2 (19m 3s):
I just wanted a decision to be made at that point. Number one. But on top of that, we had asked them, okay, can you do three quarters of the pizza with mushrooms and then a quarter without it? And he said, oh no, I don’t think we could do that. I think they could do that. It’s not really that hard. It’s a deep dish, just separate the toppings. But nonetheless, I’m not in the pizza business. So I don’t really know the intricacies of it. So we decided on the half hat, but to Kim’s point on what she was saying, I mean, this is Chicago style, deep dish. So even an individual one probably could have fed two of us. So it would’ve just been a lot.

4 (19m 34s):
It was just a pain in the ass and I was being a pain in the ass.

2 (19m 38s):
So I stepped up and then we ended up doing half, half, and it was actually really good pizza. I liked it a lot.

3 (19m 44s):
I actually had a little bit of a freak out while we were eating the pizza too.

1 (19m 47s):
He did,

3 (19m 48s):
He did because you know, he gave Kim her slice Sans mushroom. He gave me a slice with mushroom. He gave Brittanie a slice with mushroom and then he gave Jamal a slice with mushroom as well. And as he handed Jamal the slice with mushroom, he said, oh, I’m so sorry, sir. Like this one has mushrooms. And so Brittany was telling Jamal, that’s fine. All eat one without the mushrooms. And Jamal flipped out. I’m the one that volunteered to have no mushrooms. I’m going to eat the slice without mushrooms. And so Brittanie and Jamal were kind of going back and forth at it.

2 (20m 20s):
So what you’re saying is Brittany caused my freak out because we had already decided I was just going to do it. And then she goes changing the plan. When I know she wanted mushrooms,

1 (20m 28s):
I was just trying to help you out. Cause I know how much you like mushrooms. Okay.

4 (20m 31s):
At the end of the day, if we just didn’t have mushrooms in this world, none of us would’ve had a freak out and we would have been fine.

2 (20m 38s):
Or if you just tried mushrooms,

4 (20m 39s):
I would have tried them. And I’m not going to get sick. Like you guys did the last time we were in Mexico. Okay.

2 (20m 44s):
And those were uncooked portabella. That’s not compare them to cooked mushrooms in a pizza. Nonetheless, moving on from Lou Malnati is it was recommended to us again by multiple people. And I enjoyed it a lot. I don’t think it’s the best pizza I’ve ever had, but definitely when in Chicago it’s a must try. I would say,

4 (21m 3s):
You know what I learned about it afterwards that Lou Malnati is around the Superbowl. We’ll actually mail pizzas around the country. We could order like frozen pizzas and have, I don’t even know if they’re frozen, but we can order the pizzas.

1 (21m 16s):
So to work off our pizza and all those calories that we just indulged in, we walked to Millennium Park and it was about a 30 minute walk because we wanted to go see the bean or me.

4 (21m 28s):
Yes. We all flick the bean. We all

1 (21m 30s):
Flick the beans.

4 (21m 31s):
The bean was so cool. It’s just like a structure in a park, but it was amazing. And mesmerizing,

2 (21m 37s):
Well, it’s a piece of art and it’s actually called the cloud gate and it gets the nickname, the bean, because it shape is like a bean, but it’s really cool to see in person and even look at it and play with it. And by play with it, I mean,

4 (21m 51s):
Touch it, go in it.

2 (21m 53s):
Yeah, because it reflects everything from a three-sixty direction. So it will reflect at your eye level. It will reflect the skyscrapers down on it. You can go under it. So when you go under it, it almost creates like a kaleidoscope mirror effect in there. So everybody’s trying to take wacky photos and do different things in there. It was just really cool to experience a Chicago tradition that many people do go into see the bean.

1 (22m 19s):
Yeah. And so when you go to the park, everyone’s clustered at the front, but I would encourage you to walk under it and around it, because on the backside of it, there were less people I feel like. And additionally, we were able to lay down underneath the beam, which was a fun experience. We got some good photos of us acting like we were surprised.

2 (22m 39s):
What do you mean by surprised?

4 (22m 40s):
It looked like we were like on a roller coaster almost.

1 (22m 43s):
Yeah. We were laying down with our feet up and we all have like our mouths open, like run a ride.

2 (22m 51s):
But like I said, it’s more enthralling for the stupid stuff that you do in front of it, with the reflections it’s really cool to see and do.

4 (22m 58s):
And then that’s pretty much what you do when you’re there. You get in, you get your pictures, you move along. We did want to go to Cindy’s rooftop bar, which overlooks that part of the park

2 (23m 9s):
Across the street from

4 (23m 9s):
Millennium. It’s a really beautiful hotel. I think it was in, but the wait was a little while. So if you are going and you want to hit up Cindy’s rooftop bar, make a reservation ahead of time. Moving along. We did a lot of walking on this day. So then we walked along the riverfront to Navy Pier,

1 (23m 26s):
Which was another 30 minute walk from the park to Navy Pier.

4 (23m 29s):
And what’d you guys think about Navy Pier?

2 (23m 31s):
I get that. A lot of people go there. I don’t understand why. I’m glad we did it just to do it. When we go back to Chicago, I wouldn’t do it again. It reminds me almost of a pier 39 and San Francisco, lots of places to eat and shop, but I too impressed with it necessarily. The one thing that I did like about it as it did have an open container rule there, cause I did see a lot of people strolling the pier, having a beer or a cocktail in hand, which I actually liked that ambience. But nonetheless, other than that, it’s just a place to stroll around. They have a Ferris wheel that you could ride. We didn’t do that, but something to do and walk around and experience everyday city, life of Chicago. But if I was to go back, I would definitely wouldn’t go there.

3 (24m 11s):
When you get to the end of the pier, you have a great shot for a picture with the city behind you. So it is a great photo shoot place.

2 (24m 18s):
That is true.

1 (24m 19s):
I actually enjoyed walking along the riverfront more than I did the Navy Pier. And after being on the architectural boat tour and being able to walk the riverfront, it just gave a different dynamic and perspective. And I loved how much green space that they were able to incorporate along the river. And they had bars and restaurants and places to go to and experience on the riverfront, which was really,

4 (24m 43s):
And it was all decorated with fall and pumpkins and it was very festive for the fall season.

3 (24m 47s):
I can only imagine how pretty it is when it starts to snow. I mean, it’s already beautiful, right? So like add in the snowy elements. But if you keep the warm weather while it’s snowing,

2 (24m 56s):
I don’t think that’s possible. It’s going to be frigid and Colt, but I would love to experience The Chicago. I don’t want to be there during a deep freeze, but I think it would be fun to walk around the city when it’s mildly cold and snow. And I don’t want to deep freeze, but I think that would be fun

4 (25m 10s):
To do no

2 (25m 11s):
Polar vortex for me. I’d like to keep that out of it. But after Navy Pier, we ended up walking to the John Hancock building.

3 (25m 18s):
And I just say for all the steps that we got in, how comfortable were your shoes, Jamal?

2 (25m 24s):
Well, I made the classic mistake of wearing new shoes for the first time on a long walking day. Usually I don’t have that problem, but my toe started to really hurt them. But

3 (25m 34s):

4 (25m 36s):
Those were hurting too. They weren’t new.

2 (25m 38s):
I trooped through it. So it’s not that big of a deal, but nonetheless, I like my new shoes. I thought they were fashionable stylish.

3 (25m 44s):
I liked them very

2 (25m 45s):
Much. So it was worth the pain.

3 (25m 47s):
There you go. Yeah. So we did walk to the John Hancock building and we walked along the lake to

2 (25m 52s):
Yeah, we did. So from Navy Pier along the lake, we walked and that was actually the first time we reached in and touched like Michigan, if I’m honest. Yeah.

4 (25m 59s):
It’s so cool that you can just look out and not see the end of it. It’s so massive,

2 (26m 4s):
Like an ocean.

1 (26m 5s):
So we were walking along the side of the lake and we needed across to the other side and we were trying to figure out how to cross the road because there wasn’t a crosswalk or anything and it was blocked off. And so we see a tunnel to go underneath the road and come out the other side, Cena, how was the tunnel?

3 (26m 22s):
Oh my goodness. Pro tip walk in the middle of the

4 (26m 26s):
Tunnel. Run through it.

3 (26m 27s):
Yeah, seriously. Okay. So we’re in there and I was kind of walking more towards the side of the tunnel and all of a sudden I look up and there was a big ass mother, fucking spider, ready to hit my face. And so I screamed so loud, ran to the middle of the tunnel and then ran the rest of the way

4 (26m 47s):
All over the tunnel.

2 (26m 48s):
And there was tons of big spiders in that tunnel, but nonetheless, they were confined to the corners in their webs. They weren’t hanging down in the middle or anything like that. So all this hoopla and fun on our way to the John Hancock center was for one reason, it was recommended to us to go to the 96th floor where they have the signature lounge and from the signature lounge, you’re supposed to get a beautiful view of the Chicago skyline and it’s free to go up there, but it is a bar and you obviously have to buy yourself a cocktail. Now we did this because it was recommended to us by some Chicago winds and people who have been there before. And they say, instead of going to the top of the Sears tower, which is now named Willis tower, but all Chicago and still call it the Sears tower, you have to pay a $30 admission fee to go to the top.

2 (27m 31s):
And that’s the tallest building in the city. And we thought, well, instead of paying $30, just for an observation, let’s go to the 96th floor of the John Hancock building and get ourselves a cocktail. And unfortunately the room that they put us in only gives us a one-sided view of the city to north Chicago. So it doesn’t give us any views of the backside with the majority of the skyscrapers. You just get a view of lake Michigan and a little bit north going towards Wrigley Field.

1 (27m 58s):
This isn’t the room that they put you in. This is where the bar is. It’s not like we were in a designated section. This is the signature

4 (28m 4s):
Lounge, the lounge. And it was a pretty view.

2 (28m 6s):
No, no doubt, no doubt. I’m just letting everybody know that I was under the impression when we went up that we’d probably have a 360 degree view. And we did

4 (28m 15s):
Right underneath the floor, 95th floors where they have the dining area and they do have that view of the other side of the city from there.

2 (28m 22s):
But you have to eat in the restaurant.

4 (28m 23s):
Exactly. So what did you guys think about the lounge? Because I know what I thought.

3 (28m 27s):
So it’s called the signature lounge

1 (28m 29s):
And I was expecting to be almost under dressed for going in there. But once I actually got in there, I felt like I was overdressed and it was outdated

4 (28m 39s):
And I thought it was a bowling alley lounge. It felt like a bowling alley lounge to me,

2 (28m 43s):
The old wooden tables kind of dingy chairs.

4 (28m 48s):

2 (28m 49s):
I mean, for the

4 (28m 51s):

2 (28m 51s):
For the John Hancock building, I feel like I would expect a little bit more, but we did go down to the floor below to the restaurant and the restaurant itself seemed nice. It did give you the 360 degree views. But again, when they advertise something as free with the view, I guess we learned our lesson on it because they charged us overpriced cocktails at $18 a cocktail.

3 (29m 10s):
That weren’t good. That at least mine wasn’t bad.

4 (29m 13s):

2 (29m 14s):
So that’s why I just want to say pro tip on my end. I don’t know how the ladies felt on it. In hindsight, when we go back, I think I should have just paid the $30 in gas.

4 (29m 23s):
I mean, I think I still do it. I would probably dinner there. Honestly.

2 (29m 27s):
Why would he dinner there too? No doubt. I’m just saying if you’re thinking about being savvy to save money, kind of how we got the recommendation of, I just think the people who told us that our people who live in Chicago or lived in Chicago and they think to themselves, oh, it’s just a building. It’s a tourist trap. It’s nothing special to them. But in hindsight, I think I would have enjoyed an observation deck view of a 360.

4 (29m 48s):
I do want to say we went there around four o’clock and we were able to get good views of the city from the windows that we did look out of when we left, it was about five 30 and all of the fog had rolled in from a storm that was coming in. There was absolutely no view. It was completely great out, but

3 (30m 7s):
You know, we’re so high that all you see are clouds that you don’t even know it’s raining. So when we finally got down, we’re like, oh wow, it’s raining. Yep.

4 (30m 15s):
And what did we do?

3 (30m 16s):
I think you guys had a freak out.

2 (30m 19s):
No, we knew after cocktails, but before we get into that, I just want to say fun, little bit of trivia about the John Hancock center. Do you know that that’s the building that Chris Farley was found dead and he lived in that building because it’s yeah.

3 (30m 34s):

2 (30m 35s):
Part residential, part commercial as well. And Chris Farley had an apartment in there and that’s the building he was found at that

4 (30m 41s):
Is Chris Farley.

2 (30m 43s):
Are you being serious?

4 (30m 44s):
Maybe? I know. I don’t know who Chris really is. This man

2 (30m 48s):
He’s like one of the most famous comedians. He died of a drug overdose

3 (30m 53s):
Down by the

2 (30m 54s):
River. He was on Saturday night live. He was in Tommy boy. He was in a lot of early nineties comedy movies. Wow.

3 (31m 2s):
You were just a shock. This was while you were joking.

2 (31m 6s):
I really thought she was joking.

3 (31m 8s):
Yeah. Oh my gosh. I was ready for you to be like, just kidding guys. Wow. Chris Farley was a huge,

4 (31m 13s):
I mean, I thought you guys were talking about a wrestler, but

2 (31m 17s):
No, we’re not. But to get back to it, it had started to rain. I think sane is saying, she thinks maybe we had a little bit of a freak out of sorts, but the plan was for us to go to a specific, fast food restaurant that Brittanie, and I really, really wanted to eat at

3 (31m 34s):

4 (31m 35s):
And geeking out over. I was

2 (31m 37s):
Kiki. I was geeking out over it because Brittanie and I first tried it along with Zayna when we were in Africa. Now this restaurant chain, I would equate it almost like a Boston market, but it’s not a Boston market. Cause it’s not rotisserie. So it’s hybrid KFC, Boston market point being it’s chicken, but it’s not fried

4 (31m 55s):

2 (31m 56s):
Sauce. Chicken. Yeah. Not artistic. Yeah. Hot sauce, style chicken and

3 (31m 59s):
African hot sauce. Style chicken.

2 (32m 2s):
Yes. And they only have it in a few cities in the United States and Chicago is one of them. So when we found that out Brittanie and I were like, oh, we definitely want to go back. So after the John Hancock center, we were going to go get dinner there. And then it started to rain and we were like, okay, should we walk it? Should we get a Lyft, Lyft? And Uber were having surcharges because of the high demand, because it started to rain and we knew it wasn’t too far. And yet they wanted to charge $25 for a ride to go half a mile. And we were being cheap and saying, I’m not going to pay 25 bucks for half a mile. So we were kind of in a wait game, sitting in the lobby, the John Hancock center waiting for it to die out until we finally said, fuck it.

2 (32m 43s):
Let’s walk in the rain, which we

3 (32m 45s):
Did. Let’s do it. Let’s do it. Let’s do it.

1 (32m 46s):
And by walking the rain, you mean running in the rain because that’s ultimately what we did on our way to Nando’s

3 (32m 51s):
In all fairness, the first half it did stop raining. So we were good. And then

2 (32m 55s):
It was still raining. It wasn’t as hard.

3 (32m 57s):
Okay. Well then it’s not until we got around the corner from Nando’s that it started to pour. And then by the time we got to Nando’s we were like soaked.

1 (33m 4s):
Sure. We’re

2 (33m 5s):
But how was Nando’s I can say I loved it. Delicious. I

3 (33m 8s):
Love the Perry Perry sauce.

1 (33m 10s):
Yeah. What’d you think cam as your first experience,

4 (33m 13s):
It was okay.

1 (33m 13s):
Would you eat again?

4 (33m 14s):
I would eat again, but I wouldn’t go out of my way to

3 (33m 18s):
Kim, would you have rather had a hot Italian and Italian

4 (33m 22s):
Beef sandwich? It

2 (33m 23s):
Knows what you’re thinking

3 (33m 24s):

4 (33m 27s):

2 (33m 29s):
And those for the wind.

1 (33m 31s):
So after Nando’s we did decide to take a Lyft back to our Airbnb. However, we really wanted to get out Kahal in particular, we were looking for white claws.

4 (33m 45s):
Okay. Jamal had never had white claw and I am white clubs c’est

1 (33m 49s):
So I looked for the nearest liquor store tour, Airbnb and I had the driver drop us off there rather than to our Airbnb so we can get the white claw. And then we walked to our Airbnb from the liquor store,

3 (34m 2s):
No law with the

4 (34m 3s):
Claw. Ain’t no love place when you drink in class.

2 (34m 6s):
So tagline

4 (34m 8s):
There’s a comedian, pretty famous comedian. Now who

2 (34m 11s):
Not as famous as Chris Farley. I’m sure.

4 (34m 13s):
Well there’s guys like up and coming, but he made a skit about white claw. It’s hilarious. And that’s his thing. And so I went viral,

1 (34m 20s):
So we tried the lime and mango. And when I say we, I mean, Jamal and I for the first time tried to the Lyman man, the

4 (34m 27s):
Word act,

1 (34m 28s):
They were delicious. I enjoyed them.

4 (34m 30s):
Now you guys are hooked, aren’t you?

1 (34m 32s):
Yes. And so we played Rummy and how to white claws before we ended our evening.

2 (34m 36s):
Well, the reason why we called it a night early, we had plans for the next day. The next day in the morning, we were going to be going to Indiana dunes national park to do some hiking. And before we can do that, we actually had to go back to the airport and pick up our rental car. The reason why we didn’t get it upon arrival was because by the time we landed, the rental car location was actually closed. So we had to go the next day, which was going to be Sunday morning. And

4 (35m 3s):
We didn’t need it for that first day. We only need it the second.

2 (35m 6s):
Yeah, definitely didn’t need it the first day anyway. But it was just kind of the inconvenience if you will of maybe going back. But we went in the morning to pick up the car

4 (35m 14s):
At the crack of Dawn,

2 (35m 15s):
The crack of Dawn.

3 (35m 16s):
No idea where to get dropped off at. It’s

4 (35m 18s):
A very creepy rideshare. Oh

2 (35m 20s):
Yeah. I’m getting ahead of myself. Yes. Let’s somebody talk about the rideshare driver.

1 (35m 25s):
So while we were walking around Millennium Park, people on the streets were handing out little cards with promo codes for their new ride sharing platform called via. And they were saying link it’s cheaper than Lyft. It’s cheaper than Uber. So I’m like, all right, can’t hurt to save a few bucks.

2 (35m 40s):
And it was $5 off your first five rides or something like that.

1 (35m 43s):
Yeah. So I downloaded the app and I request our via in the morning and I’m reading about it. And it was like, you have 30 seconds to get in the car. Once they say that they’ve arrived. And of course, you know, Kim and Zena are,

3 (35m 57s):
I was outside

1 (35m 59s):
Running late. And so finally

4 (36m 1s):
Like rolling my eyes right now, but you can’t see it

3 (36m 3s):
Just about to say, did you hear that viewers? Did you hear that? That was, those were my eyes rolling in the back of my head going Against my skull.

1 (36m 12s):
So I was telling everyone to get ready and Jamal’s like, you need to get down there. So Zaina did get down there with me. And he waited behind cause he had to lock up the house for Kim who was taking her. I was

4 (36m 24s):
Dealing with some

1 (36m 25s):
Issues time. So the guy arrives to her place and he is not friendly at all. First of all, there’s four of us and we’re going to take up every seat in his car and he has stuff all over his front seat. And I was like, Hey, just want to let you know, it’s four of us. And he’s just like, where are you going? I’m like, okay. So then I was like, it’ll be just a minute. And he did not seem to care. He looked like he was going to murder me. If I took the ride by myself

3 (36m 50s):
And Brittany even asked him, Hey, how are you doing? And he totally didn’t respond. And then said again, where are you going?

4 (36m 58s):
Thank you. Couldn’t see it in the app. Then he was driving like a maniac and we’re flying around his car.

2 (37m 3s):
It did make a quick swerve. He didn’t make a quick swerve.

4 (37m 6s):
And then he dropped us off at the rental car place in the middle of nowhere and was like, all right here, we’ll do.

2 (37m 13s):
Yeah, he dropped us off at the car return, but he couldn’t go in cause he didn’t even have a rental car. So he dropped us off out in the middle of nowhere. We had to kind of hike up and go through, find the elevator to get into the actual rental car place. So that in of itself was a debacle.

4 (37m 28s):
I think Jamal had a little mini freak out there too. Cause he didn’t want to go walk up the ramp, but he did it. He sure

1 (37m 35s):

2 (37m 35s):
We could have walked up and just find it’s in is freaking out Carter. Okay. So what walk along the side of it.

4 (37m 43s):
You want it to just go and get in a car without checking?

2 (37m 46s):
No, no, the Hertz, the Hertz one that was downstairs, that Hertz one that was downstairs had actual check-in locations in the garage. And I was under the assumption that ours Alamo was going to have the same thing if Hertz had it versus the general lobby area. So I thought, okay, we would be able to check in from there. That’s all that really happened, but

1 (38m 7s):
You can’t see my face right now, but I’m just giving Jamal this. What the fuck were you thinking?

3 (38m 13s):
And the cherry on top of all of this though, is we ended up saving money. Do you want to give our listeners that pro tip?

1 (38m 20s):
Yeah. So the night before we left for Chicago, we actually rebooked our rental car. We’ve said this before, and it was $20 cheaper the night before our flight. So we went ahead and rebooked it and canceled our old reservation. So that was great. Another tip that I learned was that when they charge you for your rental car, we only needed it for one day. So I had booked it so that we picked it up in the morning and dropped it off late that evening because it wasn’t allowing me to put in to drop it off the next day as early as I wanted to drop it off because they’re not open. So we actually learned that they charge you for a full 24 hours. And even though at this particular location, the rental car place is not open.

1 (39m 3s):
You can drop the car off at any time. So we were able to, instead of dropping it off that evening, drop it off when we left for our flight in the morning, which was clutch,

4 (39m 12s):
Which saved us from another near death experience.

2 (39m 15s):
Yeah. Well it saved us from a lift from the airport back to the Airbnb to only take another lift back to the airport.

4 (39m 22s):

2 (39m 23s):
So even us as the Travel Squad learn stuff new every day through adventures and travel. And that’s one thing that we picked up, even if your rental time is less than 24 hours for your pickup and drop off, technically when they rent it to you, they have to give it to you for 24 hours.

3 (39m 38s):
Yeah. So then we went to go get our car and they gave us what a Toyota, something rogue.

4 (39m 43s):
When you had the

3 (39m 43s):
Road, they wanted to give us a tiny little Toyota. And then she said, oh, there’s

2 (39m 47s):
We got the intermediate, we got the intermediate vehicle and the intermediate vehicle could have just fit us just fine. But then she figured, oh, there’s four of you. And I don’t know if they just didn’t have a lot of reservations that day, but she gave us a free upgrade there to give us the little hybrid mini SUV of sorts. So we got a Nissan rogue

4 (40m 3s):
Gotta say backseats comfortable.

1 (40m 5s):
I know I got video of you guys sleeping in the back seat on our way home.

3 (40m 9s):

2 (40m 10s):
So after we got the car, we made the quick one hour drive to Indiana dunes national park, Kim

1 (40m 17s):
Did you know we were going to Indiana on this trip?

4 (40m 19s):
I mean, yeah, of course. No, it wasn’t until I looked at the map and I was like, we were actually crossing the state line. We’re going to Indiana. Cool. Like I’ve never been to Indiana.

2 (40m 31s):
Hence the name Indiana dunes, national park, not Illinois, But this national park is actually the newest national park in the national park system. And it’s really, really cool. It sits on the Southern end of lake Michigan. And you would think along the lake, there’s going to be sand and beaches, which there definitely is. But I was taken aback with really how forested and wooded the area was. The trail that we did, which was the cows bog trail had tons of large Oak trees. Lots of deer are in the area and well mosquitoes definitely. But nonetheless again, taken completely aback with how forest and wooded that area was along the shores of lake Michigan.

2 (41m 11s):
I just wasn’t expecting that.

4 (41m 13s):
You guys, we made a bet who would get a mosquito bite and where would it be? And I think I said my ankle, but guess where I got one, your nipple, I wasn’t topless out there. I got one right on the front of my neck.

2 (41m 24s):
No, I ended up getting three. I got two on my elbow, one on each elbow. And then one on my wrist,

3 (41m 30s):
You know, I was wearing leggings and I still got one on the back of my leg

1 (41m 37s):
Winner winner chicken dinner. The trail that we did was called the cows bog trail system. And I did the research on this trail and I was really interested in it because it described the trail as going through several distinct habitats and it was supposed to have ponds, swamps, marshes, black Oak, Savannah, and beaches. And so the hike actually ends where there’s a final sand dune that you have to climb over to get onto the beach. And that’s why I picked this particular trail.

2 (42m 6s):
Well, before we were able to do the trail a shit show and sued,

3 (42m 10s):
We did a warmup

1 (42m 11s):
And a little warmup. So we get to the parking lot and immediately we get out of the car and we see that there is already a trail ahead. So we’re like, perfect. This is it. We’re going to hike this, no questions about it. And we’re probably what maybe 20, 25 minutes in, before we realize there isn’t any signs. And we aren’t following the map that I had looked up

3 (42m 34s):
Because it took us to the side of a road. And I think there was like this not argument, but this debate on whether or not we should be like a chicken and cross

2 (42m 45s):
Brittany wanted to cross the road. You know, what’s really funny is that there were a couple spots along the trail, which wasn’t the real trail that we did where you can veer to the left on, based on the map that Brittany had that was given to us by the ranger, she said everything is going to be staying straight or to the right. So we did do that.

4 (43m 5s):
Pretty sure Brittany said, I know the train. Yeah.

2 (43m 8s):
Yeah. And so we got to a second one. So we got to a second split point or fork, whatever you want to call it. And then I asked Brittanie where to go. And she says, go straight. I know the trail. And then I continue straight. And then maybe three minutes later, probably less than that. We come to a big road and I’m like, are we supposed to cross this or go down this little meandering, narrow path right here. But he’s like, I think we should cross it. Like cross it. Let me see the map. And nowhere on the map, did the trail cross a road? Brittany was really adamant about one of the process

1 (43m 43s):
When we were in the parking lot, we were supposed to cross the road.

3 (43m 49s):
Well, you guys are in such a good treat because you get to see Brittanie and Jamal have a freak out on the recording.

4 (43m 54s):
It’s hilarious because Brittanie has her phone map up. Jamal has the paper map that the ranger gave us and I walk over and Jamal is like, I don’t think this map is right. I think it’s like a mirror image it. Then the road is right here. And I look at the map after they’d been talking for a while and I’m like, you guys, this is not a mirror image map. We’re on the other side that we’re not supposed to be on. We’re supposed to be on the left side of this road. And then that’s when we realized we were on could the completely wrong trail.

2 (44m 21s):
So we had a double back the mile that we had already walked. So we added an extra two miles and I just, I just want to say very bad on the national park system. How can you put a parking lot on the opposite side of the trail and have a trail head? That’s not the trail of the trail, parking lots name, totally disoriented us. But nonetheless, we got onto the right trail hiked it, it was beautiful. And Brittany said the climax was the final hill that gives you the sand dune, overlooking lake Michigan,

1 (44m 52s):
Just a little tip guys, make sure to wear long sleeves and long pants because there are places where you will encounter poison Oak and poison Ivy along the way.

3 (45m 2s):
And lots of mosquitoes.

2 (45m 3s):

4 (45m 4s):
Yep. So we climbed down the sand dune, got to the edge of the water of the lake and just sat and enjoyed it for a moment

2 (45m 12s):
With a white claw, light

6 (45m 13s):
White claw.

3 (45m 15s):
It was so much more beautiful than what I was expecting. And I don’t know what I was expecting, but it was just so nice. It’s so huge. And you can see Chicago on the day that we were there. It was clear enough to where you could see Chicago across the lake and then you can see even see parts of Michigan. And once we saw Michigan, we’re like, holy shit, guys, that’s Michigan right there. Let’s go to Michigan and have lunch. Yeah.

1 (45m 37s):
So I looked it up on Google maps and I saw that one of the closest towns, only a 30 minute drive away. So we’re like, all right, we’re going to Michigan for lunch

2 (45m 45s):
And we’ve never been to Michigan. So we were all like, let’s go to Michigan.

4 (45m 48s):
And it had a rooftop restaurant

3 (45m 50s):
Before. Obviously we have to, you know, double back to get to the car and, you know, just because the important stuff, they do have a very nice porta-potty in the parking area where there’s a wrong Trailhead.

4 (46m 4s):
Of course you have to talk about the bathroom on this podcast or wouldn’t be the Travel Squad Podcast. Right?

3 (46m 9s):
Exactly. I would say that the porta-potty, it doesn’t have a sink and it doesn’t have soap. Some do you know, but it was tolerable the smell. And I would give it like seven out of 10

2 (46m 20s):
For what it was. It was a good port-a-potty. And I just want to say, since Zana circled back around this, before we get back to going to Michigan, all the more reason why I was confused, I always see porta-potties or toilets at a trail head. And there it is in the parking lot by that trail. So that led me to believe that we were on the right path when we weren’t. There

3 (46m 38s):
You go. All right, guys, let’s go to Michigan. Now

1 (46m 40s):
Did the 30 minute drive to Michigan. We crossed the state line while we were on Instagram, live Xena hosting the live video. And we went to the stray dog bar and grill and ate on the rooftop.

2 (46m 54s):
You have to be 21 or above to eat on the rooftop. If you go to the stray dog bar and grill,

4 (46m 59s):
It was pretty though. You could have a view of like this river that was next to it. They had a bunch of yachts out there. So for what we did get to see of Michigan for about an hour, it was,

2 (47m 7s):
Yeah, we really didn’t do much. I think we just kind of went for the novelty of saying we went to Michigan and just beyond crossing the state line, we felt like we had to do something and we were hungry after the hike. So it was let’s just eat and Michigan. And when you look it up online at advertise itself as having a rooftop bar with views of lake Michigan, which it does, but lake Michigan is far off in the distance and obstructed by some trees and condo developments. Not that I’ve ever been to Rhode Island, but the photos I’ve seen it had a Rhode Island desk feel to it. And that’s what we got when we were at the stray dog bar and grill

3 (47m 41s):
New Buffalo man,

2 (47m 43s):
New Buffalo, Michigan.

1 (47m 44s):
So then after we ate lunch, we all got back in the car and we drove back to Chicago because we had reservations at the London house for High tea. Yeah.

4 (47m 54s):
Yeah. This was my suggestion. I love doing afternoon team. We all actually enjoy it. So we made reservations for 3:00 PM, but we were on a time crunch as usual. So we jammed back to the Airbnb showered. I got ready faster than I’ve ever gotten ready in my life. Thank

1 (48m 8s):

2 (48m 9s):
It was on time for this

1 (48m 11s):

4 (48m 13s):
Actually, we said, we’re going to leave at two 30. And I was like, I think we should leave at two 20.

2 (48m 18s):
I did.

4 (48m 18s):
You were in the shower when I said it, but I said it to say that

3 (48m 20s):
I do remember you saying let’s leave by two 20. And I, I remember thinking to myself, can we do it? Can we do it? But

4 (48m 26s):
We did it. We all were ready. We zipped out of there. Jamal was pretty brave in wanting to drive the robe downtown.

1 (48m 34s):
Tell us about driving downtown. Jamal,

2 (48m 36s):
What a shit show. I don’t know what else to say. Other than that, you know, we’ve mentioned this numerous times before we’re from Northern California. I’ve driven in San Francisco. Many, many times. Everyone says driving in San Francisco is tough. It’s hard. Let me tell you something. San Francisco is a cake walk to downtown Chicago

4 (48m 53s):
And equate it to driving in downtown of New York city Manhattan.

2 (48m 57s):
I’ve never done that. I could imagine just it’s such a mass, but at least Manhattan is set up in a grid fashion. And I could probably understand it. Whereas Chicago, I don’t really know. It’s really weird how they have their streets laid out. They’ll have a top level and then they’ll have an underground level. That’s the same road. And when you have the GPS going, unless you really know the area, you can’t tell am I supposed to be on top of my, supposed to be to the bottom. There’s exits out of the bottom areas in the middle of the road. So if you’re coming and need to make a left or right, you don’t really know how you’re supposed to get up there. It’s just really, really confusing. So if you don’t have to definitely don’t drive it downtown Chicago. That’s all I have to say.

1 (49m 36s):
And we had read that there was free street parking on Sundays and Sunday was the day that we went downtown. We ended up just valuing our car because it was just much easier to,

4 (49m 44s):
We did go into one lot and I think it was like $58 would have been the cost. So we zipped out of there real quick.

3 (49m 50s):
But wait, before we went into the parking lot, what did you say, Kim?

4 (49m 55s):
Oh, it was a mall parking lot. So I was like, you would expect that the parking rates would be reasonable because it’s a mall and they want your money. So

3 (50m 1s):
Kim got us like super hyped up, like, yeah, we’re going to find great cheap parking. And then we get in and we’re like 58.

2 (50m 8s):
It was $58 for 30 minutes or more

4 (50m 11s):
Ballet was cheaper.

3 (50m 12s):
I mean, I think we going to have to pay 20 for zero to 20 minutes or something like that. Right. So there’s no way to turn around. So we have to grab a ticket and go through. And what did you say, Jamal?

2 (50m 22s):
I don’t remember. What did I say? He

3 (50m 23s):
Said, I’m not going to pay this fucking shit.

2 (50m 25s):
Oh yeah. I said, if they charged me, I’m going to fight it with my credit card company

4 (50m 30s):
Time, Jamal was pissed off about something. He’s like, I’m calling my credit card company to get this charge removed.

2 (50m 36s):
Has he ever,

4 (50m 37s):

3 (50m 39s):
I mean, like we were in and out in about five minutes and it didn’t charge us.

2 (50m 44s):
I think by law, they can’t charge you if you’re in and out within the first five minutes, especially if they have no place to park in there for you and they let you go in, they can’t do

3 (50m 51s):
That, especially if you can’t even fucking U-turn.

2 (50m 53s):
Yeah. So anyway, we got out of that hot mess real quick. And after that bullshit, we just said, fuck it. We’re going to valet. So we did valet in front of the London house and the guy who was there as the valet attendant was in love with Kim. And I don’t know if he gave us a special rate or not, but I think we only paid, what was it? $26, $26 to

4 (51m 13s):
Valet with Kim

3 (51m 16s):
$26. And we all like high fived each other. And we’re like, what a steal For 2,600

2 (51m 24s):
Never been ripped off for parking so hard. And I felt like I just had a major victory right there.

1 (51m 28s):
So then we went up to the second story of the London house and we had High tea, Kim take us through with spread.

4 (51m 36s):
So this was a modern approach to High tea. And it started with a choice of maybe 10 or so decadent teas. Yours was like a hot chocolate tea was really good. I had a really nice Earl gray tea. And then they brought out the basket and they had a green tea muffin. They had a Mingo scone and then they had another chocolate scone. All of which I thought were pretty good. The green tea muffin, oh, could have been better. Yeah. The clotted cream left much to be desired. The lemon curd was bomb. And then they had like a Blackberry blueberry jam. That was pretty good too. Then we moved on to the tiered tray, which is the highlight of the afternoon tea, of course.

4 (52m 21s):
And in this, there were a bunch of weird things. One thing that I remember was an egg salad cannoli that had, what are those little fish eggs

3 (52m 30s):

2 (52m 31s):
That was actually one of my favorite things.

4 (52m 32s):
Yeah, that was good. First time I ever had caviar, man,

3 (52m 39s):
And they also had a horseradish in zucchini tart with mustard greens. And I

4 (52m 44s):
Liked that you guys didn’t like it. That

2 (52m 46s):
Was the worst thing on the tray

3 (52m 48s):
And our waiter.

2 (52m 49s):
Yeah. When the waiter came out with it, he said, oh, this one’s my personal favorite. Because again, as he sat down the tray, he was going over to the spread himself one by one telling us at what it was. He said, it’s his favorite?

4 (53m 0s):
It was delicious. It was this little mini thing with tiny little pieces of Kenya, a little flower on top. And it was so cute.

2 (53m 7s):
It was pretty garbage. I thought

3 (53m 8s):
What I loved was Brittany got the 2012 vintage, hot chocolate poo air T air. And our waiter highly recommended that. And Jamal didn’t like it. And then what else did he recommend? I liked it. There was some that, well, Jamal didn’t like

2 (53m 24s):
It. I didn’t like it. I think that was the only thing, but I know where you’re going with this story and I don’t want to take it away from you, but I am. So I tried Brittany’s tea and I didn’t like it one bit whatsoever. Oh yes. I remember the second thing now I asked him, I said, oh, do you guys have any clotted cream? And he said, oh, let me go check in the back. Because when he brought it out, he described it as creme fresh and it definitely had the texture of it. And so I asked him again, do you have clotted cream? He said, let me go check in the back, comes back and says, oh, that actually is the clotted cream. We usually do do the crim fresh. And that’s what I thought it was too. I described it as that, but that’s the clotted cream. I said, oh, okay. Thank you.

2 (54m 4s):
And then when he walked away, he said, oh, that’s definitely not clotting.

4 (54m 8s):
Not at all.

2 (54m 8s):
Definitely wasn’t clotted cream. So after having experienced that and then trying Brittany’s tea and realizing it was garbage, I said, Oh, in my opinion, to each their own, I can smell.

3 (54m 19s):
I guess the Marusha has half of the same palette because it wasn’t my thing.

2 (54m 23s):

4 (54m 23s):
This tells me a lot about your palette.

2 (54m 26s):
That’s not what we were saying all about each other when we were there. But anyway, once I tried the tea, I said, you know what, screw that I’m going to try the zucchini tart thing or whatever it is, because if he thinks this is his best thing, I bet you it’s trash. And so I ate it and it was the thing that I hated the most on

4 (54m 42s):
It. It was my second favorite thing was that there was a spec crepe, which was interesting. There was a little mini slider with bison. That was interesting. It was almost like jerky. And then there was this weird little chip thing that was very sure. And it was a Lotus chip. It had little grapes, it had a call for a crumble. It was very odd. It reminds me of something you see in one of those space movies where they’re like this little drop is a cheeseburger. And it was like, no, this isn’t food. But anyway,

7 (55m 10s):
The next period,

3 (55m 13s):
The spec crepe, he described as what was it again?

4 (55m 18s):
It was like a spec mousse and then it had

2 (55m 21s):

3 (55m 22s):
That’s it. Okay. Okay. So he described it as a BLT and I didn’t realize that it was moose. So when I took a bite of it, it was just very, the texture didn’t hit the spot.

2 (55m 33s):
Yeah. For me, the modern approach to High tea really didn’t do it for me whatsoever. The tea itself was good, but in terms of their actual sweets and savories that they had on the tray left much to be desired. Yeah.

4 (55m 45s):
This weights are pretty good. The best part about it was that I got a free glass of champagne.

2 (55m 49s):
Yeah. He told us what the price was. Kim ordered it. And yet when he brought out the bill, didn’t put it on. But the selling point of the High tea, if there was one is the view that you get from the London house overlooking the Chicago river

3 (56m 4s):
And the Trump tower,

2 (56m 5s):
Trump towers right there. Right. But beyond that, it has a beautiful lineup of the bridges. And from the level that you’re on, you can just see them all lined up in the back. And it was a really cool view of Chicago.

1 (56m 16s):
So if you guys want to skip out on the T because you didn’t find our description was that appetite thing, the London house does have a rooftop

4 (56m 24s):
Bar, a great rooftop

2 (56m 26s):

1 (56m 27s):
So go up to the rooftop and look out, grab a drink, look out at the views. It was beautiful.

4 (56m 33s):
Has a very hipster vibe and amazing backdrop for photos.

1 (56m 37s):
And so we figured while we’re downtown, why don’t we take advantage of our $26 valet parking and walk around the river again? So we just walked around downtown a little bit more before heading over to Wrigley Field.

4 (56m 49s):
Yeah. The Riverwalk was awesome. People just drinking, eating and enjoying life was so beautiful. But you can’t go to Chicago without seeing Wrigley Field.

2 (56m 57s):
Yeah. So Wrigley Field was Kim and I is thing that we wanted to do because Kim and I are more baseball fans than Brittanie. And Zayna

4 (57m 4s):

2 (57m 5s):
Yeah. What’s more iconic than Wrigley Field, maybe Fenway park, but Fenway parks and Boston. So in Chicago, we went to go see Wrigley Field and around Wrigley Field, even though the Cubs had already been eliminated, they didn’t make the postseason. Didn’t make the wild card. The area around Wrigley Field is called Wrigleyville. And it has a really awesome vibe in terms of bars, nightlife, restaurants. So we went to go see the stadium, walk around it, just experience the ambience of the area.

4 (57m 35s):
And this is also where we got to experience a classic Chicago hot dog.

1 (57m 39s):
What did you think, Kim?

4 (57m 40s):
I liked it. Yeah. I was into it. The pepper, like give it a nice kid.

1 (57m 44s):
I actually enjoyed it too, but we only got two hot dogs amongst the four of us because we had just finished with afternoon tea. So we just wanted a quick little buyer

4 (57m 54s):
Saving room for all that Italian beef

2 (57m 59s):
Telling be filled you up off.

1 (58m 2s):
So after we had our hot dog Xena, what was on your list of musty?

3 (58m 8s):
One is you go to the family matters house so bad. I don’t think you guys know Jamal. And I grew up watching family matters. Yes. I mean, even to this day, Jamal and I still quote that TV show.

2 (58m 22s):
You’re lucky. That was a clip on, I know you get the reference. I know

3 (58m 27s):
Jamal and I, because we grew up together because we watched the same things. We will move and especially family matters quotes all the time. And I know that Kim and Brittany sometimes look at us and they’re like, huh, but Jamal just gets it.

4 (58m 41s):
Right. You never know what you guys are referencing.

2 (58m 43s):
It gave me the crazy look when I said the thing about the clip on right now, I saw you and Kim look at each other,

3 (58m 49s):
Brush your teeth.

4 (58m 51s):
Only one. I really know.

3 (58m 55s):
So anyways, I really wanted to see the family matters house. And so we definitely went there. We didn’t know whether or not it was going to be up because we read an article that in 2017, it was approved to tear the house down. They tried to save it, but it was going to be easier to build a new condo building in the spot than to renovate it. So we were like, okay, well, is it still going to be standing or is it going to be the new house? So it did turn out to be the new house, but they do pay homage to it. By having the family matters, logo on the building and going to the building. I kept playing the family matters theme song. And you

4 (59m 32s):
Probably listened to it like 30 times. It was

3 (59m 34s):
So fun. How did it knock it? You guys in the moving,

2 (59m 38s):
I enjoyed it, even though that’s just the outside exterior and they never filmed a thing in that house. It was still exciting to see because it was nostalgic for me. I grew up watching that TV show as a kid, every Friday, TGI family matters. That was my favorite one on the lineup.

1 (59m 52s):
It might not have gotten Kim in the mood to see the house, but it got her in the mood for a Italian beef.

3 (59m 58s):
Finally, you guys, we keep teasing you with all this Italian beef. And now we’re going to take you to the moment where we put it in our mouth.

2 (1h 0m 5s):
Kim was the one really hankering for the,

4 (1h 0m 7s):
My friend. Tony was like raving about this Italian beef sandwich. Like you have to have it go to Portillo’s is the big place there to get. It’s a fast food restaurant, but it kind of had like a fifties Hollywood vibe. I don’t know. Anyway, we finally went on our last night. Very last thing we did. It was very busy there. And so we were like, this is a good sign. Seems popular. We get up there. We order, you got to know, it only comes with beef and odd Jew sauce, which they call gravy, which is very confusing. So you got to put cheese on it. If you want it, you gotta put peppers on it. If you want that,

2 (1h 0m 40s):
That’s extra. Both of those things cost.

1 (1h 0m 42s):
Yeah. And then they have sweet peppers or hot pepper peppers

4 (1h 0m 46s):
And both what

1 (1h 0m 47s):
Kind of peppers do I want for my Italian beef?

2 (1h 0m 49s):
And when I asked the lady that when I bought my peppers, I said, which one’s better. She just didn’t even verbally answer. She tried. And I’m like, oh no.

4 (1h 0m 56s):
Yeah. Service was ma in any way, we got our beef and There’s just so much beef. And honestly, like it was a let down.

3 (1h 1m 5s):
Could you not handle all that beef? I

4 (1h 1m 7s):
Took half the beef out.

1 (1h 1m 8s):
Couldn’t actually, when she got her sandwich, she was rummaging through her beef

4 (1h 1m 13s):
Stack and I was rubbing the beef and

2 (1h 1m 17s):
Italian beef was,

4 (1h 1m 19s):
Yeah, I’ve had better beef.

2 (1h 1m 25s):
I’ll tell you what though. I definitely wasn’t a fan of that either

8 (1h 1m 30s):
Kim, you killed it with,

1 (1h 1m 34s):
So Kim, what did Tony say when you told him about your Portillo’s experience?

4 (1h 1m 39s):
Well, I like Philly cheese steak. So I told him, yeah, we went there. You’re going to hate me for saying this. But I think that Philly cheese steaks are better. And all he said was, fuck you.

3 (1h 1m 49s):
I didn’t get a sandwich. Cause at that point, like I was so stuffed, I was Stofle. So since I was so stuffed and so full, I thought, why don’t I get a milkshake? So pro tip, if you’ve never been there, I was waiting and waiting and waiting. Everyone was getting their food, except for me

2 (1h 2m 2s):
Calling numbers.

3 (1h 2m 3s):
Exactly. Yeah. So you order in one side of the restaurant and then you go to the other side to pick it up and that’s where they’re calling your numbers and they weren’t calling mine. So finally I went and I was like, Hey, everyone’s been pretty much called who came after me? And so if you order just a milkshake or a drink, you have to go up and give it to them. Otherwise it’s not going to be on their screen. And I got the vanilla milkshake and it was not very good. In fact, to be vanilla latte that I got with Kim at the step-down cafe was better.

4 (1h 2m 33s):

2 (1h 2m 35s):
Portillo’s just letting him down on the beef and everything. Huh? I

3 (1h 2m 38s):

2 (1h 2m 39s):
So that called it an evening for our last evening in Chicago. And we had an early morning flight, luckily with the pro tip, we just discovered we were able to take the rental car back. And even though it wasn’t open for turn the vehicle there, but before we caught that flight home, I just want to give us an opportunity to say any last thoughts or anything about the trip

3 (1h 2m 60s):
Party foul on our end. We forgot that home alone was filmed in Chicago. And so next trip we’re coming for that house to check it out.

2 (1h 3m 7s):
Yeah. I said that in the morning, as we were driving to the airport, I said, oh shit, we didn’t go check out the home alone house.

3 (1h 3m 14s):
So no, I mean, great trip guys. Next time we’re going, we’re going to see the home alone house.

4 (1h 3m 19s):
Yeah. I definitely give Chicago 10 out of 10 would return love it.

1 (1h 3m 22s):
Absolutely. I agree. It was one of my favorite cities now that

2 (1h 3m 25s):
I was really pleasantly surprised. I knew I was going to like Chicago. I didn’t know how much and I definitely do want to go back.

4 (1h 3m 31s):
Well, we’re not going to have a question of the week this week and I’m really sad about it. But if you want to ask us something, you can DM us or comment on our Instagram at Travel Squad Podcast, and we’ll get it into the next episode. But thank you so much for tuning in and listening. We had so much fun sharing our trip with you. We hope you enjoyed learning about Chicago with us.

2 (1h 3m 51s):
Please subscribe to our podcast, leave a review, tell us what you like and tune in every travel Tuesday for new episodes.

3 (1h 3m 58s):
And if you aren’t already be sure to follow us on Instagram at Travel Squad Podcast, send us your questions there too. And join us live. As we get up to our crazy shenanigans, traveling

1 (1h 4m 7s):
And make sure to pack your bags and grab your passports. Because next week we are taking you chip Bennetts Italy

4 (1h 4m 13s):
With Tahlia. Bye everyone.

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