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?

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?