There are endless things to do in Chicago and the city surprised us (in a good way) with its bustling downtown core, expansive green spaces, modern art displays, Michelin-starred restaurants and charming neighbourhoods!
No matter your age or travel style, you’ll find sights and activities in Chicago that will pique your interest. It’s no wonder the city is firmly on the list of the 101 best places to visit in the US.
We recently spent a week in the Windy City and could have lingered much longer. With so many exciting things to do in Chicago (and eat!), try to give yourself at least 5 days to explore.
And, contrary to belief, this city is actually one of the best places to visit in January due to having so many indoor sights and amazing festivals during that time.
In this article, I’m going to list not only the obvious things to do in Chicago, but some of the more off-track sites and experiences that we had — and highly recommend.
Note: Don’t miss our travel video of Chicago at the end of this post!
Top 25 Must-Experience Things To Do in Chicago
Here’s my guide for the top 25 things to do in Chicago during your next trip after being shown around the city by a group of locals and the Chicago Tourism Board.
1. Walk – Everywhere!
I had to put this first on the list.
Taking transport is a great way to get around the city, but by walking, you’ll be able to experience all of the in-between bits that makes Chicago so great.
Plus, you’ll be able to burn off some of those calories you’ve consumed after eating so well!
Gaze up at the towering skyscrapers in the downtown area, or saunter down quiet streets in one of the 77+ surrounding neighbourhoods.
There are no real hills in Chicago, the sidewalks are well taken care of and you don’t need to worry about falling off any uneven curbs. If you get tired, call an Uber or hop on the train.
2. Attend a Festival
Chicago is known for hosting many, many festivals.
There are too many to list here, but if you’re interested in music, food, fashion, film, sports, culture, flowers and everything in between, you’ll find a festival that you enjoy.
During the summer months, don’t miss these events:
1. Taste of Chicago
This food/music festival has been running since 1980 and is the largest food festival in the world!
Here you’ll enjoy cuisine from around the globe — Indian, Thai, American, Caribbean, Mexican, European, and…