What to Do in Chicago (2019)

This post has information on the best things to do in Chicago. Use this guide to find information and inspiration about what to do in Chicago at night, by month, and plan a budget or kid-friendly visit.




Planning a visit to Chicago can be overwhelming with the sheer number of world-class attractions. Our suggestions for the top things to do in Chicago are listed below.

For more ideas on top popular attractions, check out our comparison guide on tourist discount passes, which could help you save money on entry fees. 

(1) Take a Sightseeing Tour

The best introduction to Chicago is to take a tour. Free Tours by Foot offers walking tours of Chicago of various neighborhoods, including the Loop, the Riverwalk, and specialty tours like an evening Chicago Ghost Tour.



If you’re looking for something a bit more exciting than walking, there are many ways to explore the city:

Foodies can get excited about Chicago’s culinary culture on food tours, as well. You can sample your way through different neighborhoods with these self-guided food tours:

(2) Learn about Chicago Architecture

One of the top things Chicago is known for is the diverse and impressive architecture you’ll find around the city. Learn about the different styles and time periods on a guided Architecture Tour of Chicago.



Just as there are many diverse bridges, buildings, and structures, there are diverse ways of seeing it all and learning about the architects. Architecture tours come in multiple forms like river tours, which give an interesting perspective, as well as free walking tours.

The biggest architecture enthusiasts will enjoy the Chicago Architecture Foundation’s over 3-hour bus tour

(3) See a Concert

There are an abundance of great venues where you can find live music in Chicago. The city has a wealth of local bands and also frequently attracts big-name artists.



If you’re interested in going to a concert, make sure to check and see what’s on at the following venues:

Click here to find all concerts in the city. No matter the genre you’re into, we’re sure you’ll find it!  

(4) See a Pro Sports Game

Chicago has multiple well-loved professional sports teams, which means that no matter when you come to the city there will most likely be a game happening somewhere. 



Click here to see all the matches in Chicago.

Many of these teams will play evening games during their regular seasons, so this could be an excellent activity to enjoy after dark.

For more things to do in the evening, please read our nighttime activities section.

(5) Go to the Theater

Chicago’s theatre scene is a close second to New York’s Broadway (well, we think so!). The best way to see a show on a budget is during Chicago’s Theatre Week. We also recommend taking a tour of the Chicago Theatre before or after catching a show. This self guided tour of the Chicago Theatre District is perfect for theatre fans. 



The crowd-pleasing Blue Man Group has year-round shows in Chicago. If you book soon enough, you could get seats in the Splash Zone and end up covered in colorful paint! 

And comedy fans will love seeing a performance at Second City, iO, or Annoyance Theater, which all offer extremely affordable tickets! 

Find all the theatrical performances in Chicago here.

(6) Visit Chicago’s Navy Pier

One of the most well-known attractions in Chicago is the Navy Pier. It is a highlight of visitors’ visits to the Lake Michigan shore at any time of year, thanks to Winter Wonderland when it’s cold out and fireworks in the summer. 



Here you’ll find boat tours (it’s an actual pier), the Chicago Children’s Museum, restaurants, and entertainment.

Find out more about how you can spend a few hours at the pier with our post about  Navy Pier Things to Do.

(7) Find an Observation Deck

Chicago has an impressive skyline day or night. And you can see it all from a birds-eye view and marvel at the architecture from one of the city’s observation decks.



The main Observation Decks in Chicago are:

There’s something thrilling and peaceful at the same time about being so high above the ground. If you’re a fan of heights, you should definitely try out at least one. They’re included for free on at least a few of the tourist discount passes.

(8) Enjoy a Dinner or Boat Cruise

From river cruises to the waters of Lake Michigan, there are multiple boat tours available to take



One of the most popular options is to have an enjoyable lunch or dinner on the water to relax and have fun with your travel buddies or family. These lunch and dinner cruises usually last 2 to 3 hours. Many of them are family-friendly.

(9) See the Most Popular Attractions in the City

From interesting architecture and museums to public art and sports stadiums, Chicago has plenty of popular attractions to see. 



Some of the Popular Attractions Include: 

For a list of even more fun attractions take a look at the section below.

(10) Save Money with a Tourist Discount Pass

Visitors can save up to 50% on retail admission prices with a Chicago tourist pass. These services provide heavy discounts at some of the most popular attractions in the city.



Here are a few of the sites you can visit with various discount passes, which include great year-round activities such as:

If you plan to visit even a few of these attractions, you could easily save quite a few dollars as well as time, since select attractions on these cards have skip-the-line passes. To find out which city pass will save you the most, read our full post


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Chicago has some exciting nightlife and entertainment to enjoy, from tours to live music and open-late attractions.



See our full post on things to do in Chicago at night for more ideas on what to do.

For more detail, take a look at our full post on things to do in Chicago at night.


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There are plenty of things to see and do while visiting Chicago on a budget!



Read our full free things to do in Chicago post for more details. Listed in this section are our top 10 free activities: 

For more budget-friendly activities, check out our full free things to do in Chicago post.


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Visiting Chicago with the kids? Here are our top ten ideas for family-friendly activities.



Make sure you read our full family-friendly post for more trip inspiration!

For more things to do with the kids, read our family-friendly activities in Chicago post.


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Below is a list of many of the best things to see and places to visit in Chicago. For in-depth information on how to visit these attractions, simply click on the site’s name and you will find ticket prices, tips on getting discounts, and what you can see while there. 

Top Chicago Attractions:


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Find Chicago Events For The Month You’re Visiting

We think any time is the best time to visit Chicago and to make sure you know the best things to do while you’re in town.

Winter Season (Nov, Dec, Jan, Feb)

Springtime (March, April, May)

Summer in the City (June July, Aug)

Fall (Sept, Oct)


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Let Us do the Planning | Itineraries for Chicago


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