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Things to do in Chicago: Your guide to the city's best activities

Whether you're a local or tourist, make the most of this city with your checklist of quintessential things to do in Chicago.

CAF River Cruise

Looking for things to do in Chicago? We've got you. This is, after all, what we spend the live-long day doing: seeking out the coolest stuff in our city to share with you-everything from must-see Chicago attractions, parks, museums and tours to the best art galleries, brunch spotsfood trucks and comedy clubs. If you're a seasoned Chicagoan, you might feel that, sightseeing-wise, you've bean there, done that. But read on: Our to-dos are designed to appeal to both first-time visitors and experienced Windy Citizens. Besides classic experiences, such as exploring Millennium Park and eating a Chicago-style dog, you'll find some insider-y, more off-the-beaten-path suggestions, too. Now get out there and get doin'.

RECOMMENDED: The top 10 best museums in Chicago
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Explore Millennium Park.
Things to do Buy tickets

Explore Millennium Park.

Users say
  • 5 out of 5 stars
Take in the light and music display at Buckingham Fountain.
Things to do

Take in the light and music display at Buckingham Fountain.

Make like Ferris Bueller and see iconic artworks at the Art Institute of Chicago.
Things to do Buy tickets

Make like Ferris Bueller and see iconic artworks at the Art Institute of Chicago.

Users say
  • 5 out of 5 stars
Taste a Chicago-style hot dog.
Restaurants

Taste a Chicago-style hot dog.

Drink in the views at the Hancock Building's Signature Lounge.
Bars

Drink in the views at the Hancock Building's Signature Lounge.

Users say
  • 4 out of 5 stars
Take a Segway tour of local attractions.
Things to do

Take a Segway tour of local attractions.

Dine on Devon Avenue.
Restaurants

Dine on Devon Avenue.

View cutting-edge art at the Museum of Contemporary Art Chicago.
Museums

View cutting-edge art at the Museum of Contemporary Art Chicago.

Users say
  • 5 out of 5 stars
Get down at Windy City Soul Club.

Get down at Windy City Soul Club.

Root for the home team at Wrigley Field.
Sports and fitness Buy tickets

Root for the home team at Wrigley Field.

Users say
  • 4 out of 5 stars
Go to a performance of the Neofuturists' Too Much Light Makes the Baby Go Blind.
Theater

Go to a performance of the Neofuturists' Too Much Light Makes the Baby Go Blind.

Users say
  • 4 out of 5 stars
LOL at a Second City show.
Comedy

LOL at a Second City show.

Users say
  • 5 out of 5 stars
Get lost in Lincoln Park.
Things to do

Get lost in Lincoln Park.

Eat a burger to the tune of deafening heavy metal at Kuma's.
Restaurants

Eat a burger to the tune of deafening heavy metal at Kuma's.

Users say
  • 5 out of 5 stars
Things to do

Stroll around Promontory Point.

Users say
  • 5 out of 5 stars
Hit the beach. (There are plenty to choose from.)
Things to do

Hit the beach. (There are plenty to choose from.)

Go vintage shopping on 18th Street in Pilsen.
Things to do

Go vintage shopping on 18th Street in Pilsen.

Browse independent lit at Quimby's in Wicker Park.
Shopping

Browse independent lit at Quimby's in Wicker Park.

Users say
  • 4 out of 5 stars
Shake up your cocktail game at the Violet Hour.
Bars

Shake up your cocktail game at the Violet Hour.

Users say
  • 4 out of 5 stars
Get your brunch on.
Restaurants

Get your brunch on.

Eat banh mi at Nhu Lan Bakery.
Restaurants

Eat banh mi at Nhu Lan Bakery.

Users say
  • 4 out of 5 stars
Have an Ethiopian feast.
Restaurants

Have an Ethiopian feast.

Users say
  • 5 out of 5 stars
Bike the Lakefront Trail.
Things to do Buy tickets

Bike the Lakefront Trail.

Users say
  • 4 out of 5 stars
Get a diver's eye view of marine life at Shedd Aquarium's Wild Reef.
Attractions Buy tickets

Get a diver's eye view of marine life at Shedd Aquarium's Wild Reef.

Users say
  • 5 out of 5 stars
Get a natural history lesson at the Field Museum.

Get a natural history lesson at the Field Museum.

Users say
  • 4 out of 5 stars
Have an Americano at the original Intelligentsia.
Restaurants

Have an Americano at the original Intelligentsia.

Users say
  • 4 out of 5 stars
Live on the edge on the Willis Tower Ledge.
Things to do Buy tickets

Live on the edge on the Willis Tower Ledge.

Users say
  • 5 out of 5 stars
Eat at one of Randolph Street's many fine restaurants.
Restaurants

Eat at one of Randolph Street's many fine restaurants.

See stars at the Adler Planetarium.

See stars at the Adler Planetarium.

Users say
  • 5 out of 5 stars
See a midnight movie.
Movie theaters

See a midnight movie.

Users say
  • 5 out of 5 stars
Shop for farm-fresh food at Green City Market in Lincoln Park.
Shopping

Shop for farm-fresh food at Green City Market in Lincoln Park.

Users say
  • 5 out of 5 stars
Feast on Chicago-style pizza.
Restaurants

Feast on Chicago-style pizza.

Watch runners go the distance at the Chicago Marathon.
Sports and fitness

Watch runners go the distance at the Chicago Marathon.

Take a shot of Jeppson's Malört.
Things to do

Take a shot of Jeppson's Malört.

  Visit Gene's Sausage Shop in Lincoln Square, Chicago's German neighborhood.
Restaurants

Visit Gene's Sausage Shop in Lincoln Square, Chicago's German neighborhood.

Users say
  • 5 out of 5 stars
Things to do

Discover Historic Pullman.

Users say
  • 4 out of 5 stars
Visit the DuSable Museum, America's foremost museum of African-American history.
Things to do

Visit the DuSable Museum, America's foremost museum of African-American history.

Users say
  • 5 out of 5 stars
Indulge your curiosity at the Museum of Science and Industry.
Museums

Indulge your curiosity at the Museum of Science and Industry.

Users say
  • 5 out of 5 stars
Take in a CSO show.
Music

Take in a CSO show.

Swim in a Chicago Park District pool.
Things to do

Swim in a Chicago Park District pool.

Catch a Bulls game at United Center.
Things to do

Catch a Bulls game at United Center.

Users say
  • 3 out of 5 stars
Dine at a Rick Bayless restaurant.
Things to do

Dine at a Rick Bayless restaurant.

Watch improv (and future SNL cast members) at iO.
Comedy

Watch improv (and future SNL cast members) at iO.

Users say
  • 4 out of 5 stars
Cheer on da Bears at Soldier Field.
Things to do

Cheer on da Bears at Soldier Field.

See Chicago theater.
Theater

See Chicago theater.

Watch the South Siders play ball at the Cell.
Sports and fitness

Watch the South Siders play ball at the Cell.

Users say
  • 4 out of 5 stars
Karaoke with the locals.

Karaoke with the locals.

Comments

1 comments
Orin K
Orin K

One of the Best Ways to have fun on one of the Greatest Lakes in the World is to Join Sail Chicago.  It's the best bang for the buck in Learning-How-To-Sail, getting your Skipper's Card so that you can use the 24 hr phone line to rent several types of deep-keel sail boats, join other members on various sails around the harbors, take out your friends who may have never sailed before... and teach them how to help you handle the boat as you sail along the lake for several hours of great views, great fun, picture-taking, and great conversations.  Kick back and enjoy the Greatest City in America.  If you choose, you can also learn how to race, or help "crew" in a race sanctioned by official groups like US Sail.


           Sail Chicago is easily found on FaceBook, and has its own web site  for current members and interested folks.

Just Google Sail Chicago to start the ball rolling... :)