Travel Itineraries  /  Chicago Itinerary 
Travel Itineraries  > Chicago Itinerary 

This comprehensive 2 day guide has you sight seeing & touristing your way through Chicago. This guide can be used as a guide even if your trip is not 2 days. It is good for both tourists as well as locals looking to explore in their own backyard. 

This Chicago Itinerary will take you to:
-Chicago Riverwalk
-Navy Pier  
-Millenium Park
-Lake Michigan
-Willis Tower 

Where the Chicago Itinerary Goes:

               14-pages of expert advice to help you navigate your Chicago trip and maximize your experience. This guide includes recommendations to make the most out of two days in Chicago. In this itinerary you'll find recommended activities, areas to visit and restaurants in the heart of the city. 


December 2023

Last Updated:  


2 Day Chicago Itinerary
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How this Itinerary will help you

Plan your day perfectly to see the best highlights of Chicago in just one day, ideal for day trippers, those visiting for a short time, or locals exploring their own backyard.

Exact location of each attraction, estimated length of time to spend there.

Hours and best time of year for the recommended things to see and do in Chicago. 

Recommended activities, including fees, how long to allot to experience it.

Recommended dining options 

Distance and travel time between locations.

Where to eat


Follow this itinerary! We have visited different parts of Chicago numerous times and these are some of the best highlights of Chicago that we want to continue going back to.

What should I do with 2 days in Chicago?

Although this itinerary is just a quick 2 day snapshot, it is free so you can use it as a guide to make your stay in Chicago longer by adding to it.

What if I want to spend more time in Chicago?

There are so many great areas of Chicago, and you won't be able to fit them all in within 2 days. We have focused this itinerary around iconic easy activities in Chicago as we feel it captures the essence of Chicago and highlights what the city has to offer.  

What are the best areas to visit in Chicago?

No, you don't need a car in Chicago. You can easily get around Chicago using the metro, ride share apps, taxis, or busses. You can rent a car, but please note that most places charge for parking. 

Do you need a car in Chicago?

Chicago F.A.Q.

This itinerary breaks down everything in one PDF guide. The itinerary adds even more value by planning every detail of a 2 day trip to Chicago so all you have to do is truly book it, show up and enjoy the trip. We learn a lot on our trips about things that were worth it, things we wish we did, and the optimal route to take if we could do it over. You benefit from those learnings with this itinerary! Our podcast episode of Chicago, gives you highlights but not to the level of detail you’ll find within our itinerary. 

What's different about your itinerary from your podcast episode?

Very helpful tips. I know my trip to Utah will be even more enjoyable after listening to your podcast.
Thank you!

Great Travel Podcast



The Reviews


Zion National Park

2 Day Chicago Itinerary
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 Download Here