57 Coolest Things to Do in Chicago for 2026

ByVictoria Philpott Last Updated:

There are so many cool things to do in Chicago, I’ve been twice and I’d totally go back for the hat trick. I love it there. 

If you’re looking for what to do in Chicago, then read on my friend. I’ve listed all the coolest activities in Chicago worth doing so you can have the best trip ever. You’re welcome. 

things to do chicago

This big, beautiful, lakeside city in the state of Illinois deserves a whole lot of cheesy love because it’s one of the quirkiest around. Home to dozens of museums, deep dish pizza and the Obamas, Jennifer Hudson and Bill Murray, it’s just that bit cooler than New York IMHO. 

I love the fact there’s a beach, the views from the high points are amazing, and once you’re done with the bright lights of the city centre, you can go and explore the unique personalities of the 77 Chicago neighbourhoods.

Coolest Things to Do in Chicago

Visit The Bean in Chicago