Definitive Guide to Things to Do in Chicago (2019)

This post has information on the best things to do in Chicago. Use this guide to find links to detailed information about what to do in Chicago at night, by month, and plan a budget or kid friendly visit. Be sure to consider one of our pay-what-you-wish tours to explore these neighborhoods.


The Top 7 Things To Do in Chicago For the Best Trip Ever!

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 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.

Explore Chicago by Boat, Bus, Segway and Bike

If you’re not up for walking, there are many ways to explore the city.

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.

Chicago Skyline
3. See Chicago’s skyline from above

Chicago’s skyline is best scene from high up in one of the tallest buildings in the city. There are a few options to get you the best view.

Skydeck vs. Hancock 360*

4. Eat!

What else should you do when visiting a new city? If nothing else, make sure you try some of the famous Chicago Style Deep Dish Pizza, but if you’re still hungry, sample your way with these self guided food tours of Chicago neighborhoods.

Greektown Food Tour

Little Italy Food Tour

Andersonville Food Tour

Mexican Pilsen Food Tour

On a budget? You can still get a taste of Chicago with some of the Best Cheap Eats in the city. Or if you want to get background with your brunch, take one of the Best Chicago Food Tours. And when you’ve finished sampling, relax with something from a Local Coffee Shop.

5. Take Public Transportation

Chicago is too large to get around entirely by foot so we recommend experiencing the above ground elevated train, known as the El around Chicago. Before you go, be sure to learn how to use the El and other local public transportation in Chicago.

Navy Pier in Chicago6. Visit Chicago’s Navy Pier

One of the most well known attractions in Chicago is Navy Pier. With Winter Wonderland when its cold out and fireworks in the summer, it is a highlight of every visit to the Lake Michigan shore. Here you’ll find boat tours (it’s an actual pier), the Chicago Children’s Museum, restaurants and entertainment.

Chicago Navy Pier Things do Do

7. Check out a show in the Theatre District

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. Don’t only see a show, tour these historic theatres.

Self Guided Tour of Chicago Theatre District

Chicago Theatre’s Marquee Tour

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The Places You Must See in Chicago

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 be taken to another post with information such as:

  • ticket prices and ways you can find discounts or visit for free.
  • days and hours the attraction
  • directions on how to get to there.
  • tips and suggestions on how to make the most of your visit.
  • and in many cases, we include reviews of tour companies that offer tours of the attraction and self-guided tours.

As you plan your trip, you might also decide to consider purchasing a discount pass. These tourist passes help you save money by packaging attractions together for one flat price. So many of attractions and activities listed in this post are included in the various tourist passes. We encourage you to read our post comparing the different Chicago Attraction Passes. These passes are great deals for some and not for others.

Top Chicago AttractionsChicago Architecture

Free Things to Do in Chicago

Free Chicago Attractions & Museums

While not every museum in Chicago is free, there are some options on Free Chicago Museum Days.

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Make Sure Your Kids Love Visiting Chicago

A great place to start is to look at our kid-friendly itinerary.  There you will find many of the top attractions, best times to go and also alternatives depending on the age your children.  The fun never ends for kids in the Chicago.

Museums in Chicago with Kids

Below are the most satisfying and kid-friendly experiences just click on the links below to be taken to our posts on that specific attraction and you will find useful information about these attractions such as best times to go, prices and hours, discounts, directions to get there and other nearby activities. 

Lincoln Park Zoo | Lincoln Park Conservatory

Adler Planetarium

Chicago Bus Tours

Take a Bus Tour

Bus tours are great when traveling with kids because it gives the little ones a chance to rest up a bit during a day of sightseeing. Since Hop-on, hop-off bus tours generally stop at the popular attraction locations, you can use the bus to move from destination to destination and it is a lot more interesting for your child to look out a bus window then stand in a crowded subway.  

Our post The Best Hop-On, Hop-Off Chicago Bus Tours can help you decide which is best for you and your child.

Get Outside

Let the little legs run wild and get some fresh air. Even though Chicago is a large city, there are some great outdoor activities and places to visit.

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Find the Top Nighttime Events in Chicago

Chicago at Night

There are many great things to do at night in Chicago, visit our full post Top 10 Things to do in Chicago at Night.

Nighttime Tours

Ghost tours, strolls on the Riverwalk and architecture cruises on the Chicago River are just some of the great nighttime tours that you could take. Free Tours By Foot offers this pay what you like walking tour seasonally, so check out the calendar and see what other tours we have!  Be sure to check out our guide to choosing which Chicago boat tours are best, including a fireworks cruise.  We also list and compare the best night bus tours.

Take in a show at one of the Best Chicago Blues Club.

Chicago is considered by many as the blues capital of the world. As the blues evolved and developed, many talented Blues musicians left the south and spent their most influential years in Chicago. Some of those musicians include Buddy Guy, Muddy Waters, Willie Dixon, Howlin’ Wolf, Charlie Musselwhite, and Little Walter

Have a drink!

Chicago has speakeasies – fitting for the mobster history of the Windy City, some of the Best Rooftop Bars. In our Guide to Chicago Bars you can find out about historic bars, game bars and where to have a pint while playing some trivia. If you’re looking for more than just atmosphere and want to find one of the best Craft Beers, we can make sure you find a local pint.

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Discover More of Chicago


Chicago is a big city with lots of great neighborhoods that have their own style – and flavor.

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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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