50 Things to Do Chicago in 2023 | Must-Do Activities

This post has information on the most fun things to do in Chicago today, tonight, tomorrow, or anytime.

We include nighttime, free, as well as family-friendly events and activities. Let's get started!

Top 10
Nighttime Activities
Free Things to Do
Family-Friendly
Top Attractions
By Month/Neighborhood
Suggested Itineraries

TOP 10 EVENTS AND ACTIVITIES

Planning a visit to Chicago can be overwhelming with the sheer number of world-class attractions.

Our suggestions for the top fun things to do in Chicago are listed below.

For more ideas on top popular attractions, check out our comparison guide on Ermäßigungsscheine für Touristen, which could help you save money on entry fees.

1. Watch 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.

Chicago White Sox | April - October
Chicago Cubs | April - October
Chicago Bears | September - January
Chicago Blackhawks | October - April
Chicago Bulls | October - April

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.

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. Attend a Concert

There is 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 the concerts in the city. No matter the genre you’re into, we’re sure you’ll find it!

4. 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:

5. Go to the Theater

Chicago’s theatre scene is a close second to New York’s Broadway (well, we think so!). Find all the theatrical performances in Chicago here.

We also recommend taking a tour of the Chicago Theatre before or after catching a show.

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 or Annoyance Theater, which all offer extremely affordable tickets!

The best way to see a show on a budget is during Chicago’s Theatre Week.

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 things to do at the Navy Pier.

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:

Each is included for free on at least a few of the tourist attraction 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.

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.

11. Honorable Mention: Take a Food Tour

If you want help finding the best dishes in Chicago, consider taking a Secret Food Tour.

This outing includes tastings at 6 different locations, giving you a good sense of the most popular meals in the city.

Guests can expect to enjoy samples of deep-dish pizza, Italian beef sandwiches, pierogis, multiple chocolates, and more.

In addition to all the great food, you can also get an upgraded drink package if you're interested in having a few good brews along the way.

For even more great options, check our post covering Chicago food tours.

THINGS TO DO AT NIGHT

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

Most of these activities are fun things to do in Chicago for adults.

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

12. Try to Escape from The Escape Game

From an art heist to prison break to special ops, you get an hour to go through this real-life puzzle.

The Escape Game Chicago has over 2300 5 star reviews - and don't worry if you don't make it, you'll get a discount to try again!

The Escape Game Chicago is fun for all ages.

13. Take a Chicago Ghost Tour

Discover the spooky history of Chicago and hear tales of the supernatural on a professionally guided ghost tour of the city.

In addition to learning about creepy myths and legends that were born in the area, you’ll also likely hear a lot about the more disturbing criminal history of Chi-town.

14. See a Live Performance in the Theatre District

No matter when you choose to visit Chicago, chances are you’ll have several opportunities to see a musical or other theatrical performance.

For more information about the best theatres in the windy city and excellent opportunities to save money on tickets, check our post covering the Chicago Theatre District.

15. Enjoy the City Lights From an Observation Deck

There are two really great observation decks in Chicago, and both of them are open after dark, giving you the opportunity to see the city as it lights up at night.

The Skydeck is open until 10 pm in the summer and 8 pm in the winter, while 360 Chicago is open until 11 pm on weekends.

16. Watch the Blue Man Group

This troupe has set up a semi-permanent residence in Chicago, which means that you can reasonably expect them to be performing whenever you choose to visit the windy city.

In addition to being an excellent nighttime activity, the Blue Man Group is also appropriate for kids and teens, which makes it a good choice for families as well.

17. Cheer on Your Favorite Team

As we mentioned in the top 10, there are a lot of great sports teams in Chi-town.

Many of them host games after dark, making this an excellent activity to enjoy at night.

Check this list of sporting events in Chicago to find a game that begins in the evening.

18. Go to a Chicago Symphony Orchestra Concert

This city tends to attract a lot of popular musicians throughout the year.

But, if you’re a fan of classical music, the Chicago Symphony Orchestra offers one of the best experiences in the area.

In addition to performing the works of beloved composers such as Mozart, Chopin, and more, this group also hosts movie concert events in which the music from the film is performed by the orchestra.

19. Go to a Museum After Dark

Some of the museums in Chicago offer fun activities in the evening.

The MCA has a summer jazz series called Tuesdays on the Terrace which typically starts at 5:30 pm and lasts about an hour.

It’s also worth noting that the Art Institute of Chicago is open until 8 pm on Thursday and Friday.

20. Enjoy a Chicago-Style Deep Dish Pizza

This is the only city in the world where you can order an authentic deep dish pizza, so why not make this popular dish part of your dinner plans?

If you want some help finding the best slice in town, make sure to read our post covering where you can find some delicious Chicago-style deep dish pizza.

21. See a Comedy Show at Second City

The Second City Theatre is one of the best comedy clubs in Chicago, and they host several great comedy shows throughout the year.

Many notable comedians have gotten their start here, and you might even see the next rising star when you visit!

Check this list of stand-up comedy shows to see who is performing in Chicago.

22. Take a Walk on the Chicago Riverwalk

If you’re looking for an affordable activity after dark, one of the best things to do is just walk down the Chicago Riverwalk.

This is a great location to enjoy watching the city light up as the sun goes down, and it’s also one of the best spots to either begin or end a romantic date.

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

THINGS TO DO FOR FREE

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 in Chicago:

23. Take a Free Walking Tour

There are a lot of interesting things to see in this city, and many of them are included on free walking tours.

We have pay-what-you-wish services covering a variety of subjects such as the architecture of the city, the Chicago Riverwalk, the Magnificent Mile, Millennium Park, and even a Ghost tour!

Check this list of free Chicago walking tours to find one you’ll enjoy.

24. Go to a Free Concert or Festival

During the summer months, there are often several free festivals held at various public squares and parks throughout the windy city.

Many of these events will also include free concerts, allowing you to enjoy some live music without worrying about ticket prices!

Check our monthly TTD posts to see what’s on the schedule when you plan to visit Chicago.

25. Explore a Free Museum

There are several museums in Chicago that offer free admission on either a daily basis or at least once a week.

No matter what you’re interested in learning about, chances are there is a museum you’ll enjoy exploring.

Some of the most notable examples include the Chicago Design Museum, the Museum of Contemporary Photography, the National Museum of Puerto Rican Arts and Culture, and many more.

26. Spend Some Time in Wicker Park

This is one of the trendiest areas in Chicago, and it’s full of interesting shops, restaurants, and even street art.

We currently offer a self-guided walking tour of Wicker Park which includes several popular stops, including the public park itself and its statue of Charles Wicker.

27. Discover the Architecture of Chicago

The windy city is home to some of the most impressive architectural feats of modern times, including a variety of notable skyscrapers.

We currently offer a free architectural walking tour of Chicago, and there are also self-guided tours covering locations such as Navy Pier, Millennium Park and the Downtown Theatre District.

28. Visit a Public Park

There are several excellent public parks in Chicago where you can enjoy a nice walk, perhaps go on a picnic, or even take your kids to a playground.

If you’re looking for help picking the best park to visit, check our post covering 6 of the best Chicago parks.

29. Enjoy Beautiful and Interesting Street Art

You’ll find a lot of unique artwork sprinkled across this city, including both planned out sculptures and original graffiti work from street artists.

Consider using our guide to public art in Chicago to find some of the most well known and high quality artwork which is entirely free to experience.

30. Get Free Entry to Popular Attractions

Depending on which service you choose and how you use it, you could easily use a Chicago tourist pass for enough different activities that eventually anything else you used it for would be entirely free.

31. Take a Free Brewery Tour

There are several great places to great beer in the windy city, and even some breweries that offer entirely free tours.

In addition to providing details about some of the best pubs and bars in the city, our guide to Chicago Craft Beer also includes information about local breweries and the (sometimes free) tours they offer.

32. Visit the Navy Pier

There are a lot of fun things to see and do at the Navy Pier, including a variety of notable sites like the Crystal Gardens, the Miller Lite Beer Garden, a Ferris Wheel and more.

If you’re looking for help finding the best places to visit, check our self-guided tour of Navy Pier for guidance.

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

THINGS TO DO WITH KIDS

Visiting Chicago with the kids?

Here are our top ten ideas for family-friendly Chicago activities that both children and their parents can enjoy.

Make sure you read our full post on things to do with kids in Chicago for more inspiration!

33. Take a Bike Tour of the City

With so many interesting things to see and do in Chicago, it can be difficult to get around and discover all the sites.

Thankfully, there are bike rental services which offer bicycles for both adults and children.

All bike rental companies provide helmets and other protective gear to keep everyone safe.

Kids love to ride bikes, so this is a fun way to explore the city and see some of the most notable landmarks as a family.

34. Visit the Chicago Children’s Museum

The Chicago Children’s Museum has a lot of fun, hands-on exhibits that are designed to help kids learn about the world around them.

If you’re looking for an activity that will engage the imaginations of your children, this is an excellent museum where they can go on a hunt for dinosaur bones, create art, play in a treehouse, and more.

Best of all, admission is free for children 15 and under on the first Sunday of every month, and they offer late hours every Thursday!

35. Cheer on a Chicago Sports Team

As we’ve mentioned before, Chicago is home to several great teams in multiple sports including baseball, basketball, hockey, and football.

No matter which sports your kids love, chances are you’ll have a chance to take them to a game during your trip to the windy city.

Check this list of sporting events in Chicago to find one that your children will enjoy.

36. Enjoy Family-Friendly Attractions For Less

There are a lot of popular kid-friendly activities and attractions which are included with Chicago tourist passes.

Depending on how you use these services, you could save anywhere from 20% - 50% off ticket prices.

If you plan to take your kids to locations such as Shedd Aquarium, 360 Chicago, Skydeck, LEGOLAND, Brookfield Zoo, Chicago Children’s Museum, or the Navy Pier, we recommend using a tourist pass to save money.

37) Explore the City Using Public Transportation

Chicago is well known for its public transportation system, which allows residents of the city to get around with ease.

Whether you want to hop on the train or take a bus, this is undoubtedly one of the most affordable ways to travel around Chi-town.

Check our post on the Chicago Public Transportation system for more information.

38. Spend Some Time on Lake Michigan

If you want a great view of the city skyline from the water, a cruise on Lake Michigan is an excellent and family-friendly activity.

There are several different Chicago cruises available, and there are also sailboat and kayak services you may want to consider.

39. Go to a Family-Friendly Comedy Show

Although most comedians tell jokes specifically for adult audiences, there are some comedy clubs and troupes that perform more family-friendly fare in Chicago.

CSZ offers excellent comedy shows aimed at all ages, and they also provide training for both adults and kids!

40. Take the Kids to Navy Pier

With its many family-friendly attractions and even amusement rides like a Ferris wheel and carousel, this is probably one of the most perfect locations in Chicago for children and their families.

In addition to all the traditional waterfront activities, there is also an IMAX Theatre, Funhouse Maze, the Chicago Children’s Museum, and more fun things to see and do at Navy Pier.

41. Discover the Tallest Buildings in Chicago

The windy city is home to some of the most historic skyscrapers in the world, and there are many different ways to see these landmarks.

Whether you’d rather save money with a self-guided tour, or you want to see these incredible buildings from the water on a cruise, there are several great Chicago architecture tours to choose from.

42. See a Live Magic Show

Give your kids the opportunity to be amazed at clever tricks and seemingly impossible feats performed by a live magician!

The Chicago Magic Lounge hosts a lot of great magic shows throughout the year, and these events are sure to be a hit with the family.

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

CHICAGO’S TOP ATTRACTIONS

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 Chicago 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:

MONTHLY THINGS TO DO IN CHICAGO

We think any time is the best time to visit Chicago. See our monthly posts to see what's happening when you are in town.

Winter Season (Nov, Dec, Jan, Feb)

Springtime (March, April, May)

Things to do in the Rain
St. Patrick's Day in Chicago
Easter in Chicago
Cinco de Mayo

Summer in the City (June July, Aug)

Fall (Sept, Oct)

Oktoberfest in Chicago
Join our Pay-What-You-Like Haunting History Ghost Tour
Run or cheer for the Chicago Marathon!
Halloween in Chicago
Top 10 Things to do in Chicago in the Fall

Let Us do the Planning | Itineraries for Chicago

Chicago in 24 hours | Budget Itinerary

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