Things to do in Chicago

Activities, attractions and tours

Chicago which includes a city and a high-rise building as well as a family
Chicago which includes a city, signage and heritage elements
Chicago
Chicago which includes a skyscraper and street scenes as well as a family
Willis Tower featuring a high-rise building, a city and mist or fog

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Most popular experiences in Chicago

Tours & day trips

See all 179 activities
Architecture River Tour

Architecture River Tour

Activity duration is 1 hour and 15 minutes
9.6 out of 10 with 1446 reviews
Free cancellation available
Price is S$63 per adult
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Food, drink & nightlife

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Chicago: Architecture Boat Tour with Drinks

Chicago: Architecture Boat Tour with Drinks

Activity duration is 1 hour and 30 minutes
8.8 out of 10 with 17 reviews
Free cancellation available
Price is S$54 per adult
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Private & custom tours

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Eastside Chicago The Heist Exploration Game and Tour

Eastside Chicago The Heist Exploration Game and Tour

Activity duration is 1 hour and 35 minutes
Free cancellation available
Price is S$13 per adult*
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Attractions

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360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

Activity duration is 30 minutes
8.4 out of 10 with 661 reviews
Free cancellation available
Price is S$39 per adult
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Adventure & outdoor

See all 16 activities
Rosemont: Two Flight Indoor Skydiving Experience

Rosemont: Two Flight Indoor Skydiving Experience

Activity duration is 1 hour
6.6 out of 10 with 7 reviews
Free cancellation available
Price is S$124 per traveller
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What to do in Chicago

Popular places to visit

Wrigley Field which includes a sporting event, a city and central business district

Wrigley Field

4.5/5(40 reviews)

Chicago’s world-renowned baseball ground, Wrigley Field is an iconic stadium where you can learn about the all-American sport and even catch a game.

Wrigley Field
Magnificent Mile - River North featuring street scenes, night scenes and signage

Michigan Avenue

4.5/5(14 reviews)

You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Navy Pier

Navy Pier

4/5(125 reviews)

A waterfront entertainment strip with fun diversions for both young and old, with shops, restaurants and even a Ferris wheel.

Navy Pier
McCormick Place

McCormick Place

4.5/5(36 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Millennium Park which includes modern architecture, a city and autumn leaves

Millennium Park

4.5/5(147 reviews)

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Millennium Park
Soldier Field showing a city, modern architecture and a skyscraper

Soldier Field

4/5(44 reviews)

Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.

Soldier Field
Grant Park

Grant Park

4.5/5(96 reviews)

Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.

Grant Park
Chicago Riverwalk featuring a bay or harbour, a city and a river or creek

Chicago Riverwalk

4.5/5(29 reviews)

Stroll along the waterfront of the Chicago River to pass some of the city’s most appealing attractions and appreciate how a once grim area has been successfully revamped.

Chicago Riverwalk
Six Flags Great America which includes rides

Six Flags Great America

Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.

Six Flags Great America

Areas of Chicago

Downtown Chicago which includes a city

Downtown Chicago

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Downtown Chicago
Magnificent Mile - River North

Magnificent Mile

A dazzling array of boutiques, luxury shops, famous department stores and pleasant cafés, where shopaholics can lose themselves for hours.

Magnificent Mile
The Loop - Downtown featuring a river or creek

The Loop

4.5/5(187 area reviews)

Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.

The Loop
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River North

Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.

River North
Chicago which includes a city and modern architecture

Lincoln Park

5/5(5 area reviews)

Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.

Lincoln Park
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Lakeview

4.5/5(8 area reviews)

Known for its lively bars and lake views, there's plenty to explore in Lakeview. Top attractions like Wrigley Field and Lake Michigan are major draws, and you can catch the metro at Southport Station or Addison Station (Red Line) to see more of the city.

Lakeview

 

Looking for fun things to do nearby? Check things to do near me to find and book the best things to do, fun activities, and top attractions wherever you happen to be.

 

 

Aurora which includes a city and a river or creek

Aurora

Photo by Evae

Buffalo Grove

Rosemont

Rosemont

Photo by Mark Lund

Elk Grove Village

Schaumburg showing farmland as well as an individual female

Schaumburg

Photo by Corinne Mason

Lombard

Frequently asked questions

Is Chicago worth visiting?
Offering a blend of views and dining, there's no shortage of things to do in Chicago. While you're here, head to Michigan Avenue, a major attraction in the area.
How do I spend a day in Chicago?
Once you've checked off top attractions like Michigan Avenue and Navy Pier, spend the rest of your day discovering Chicago's shopping and food scene.
What is the top tourist attraction in Chicago?
Michigan Avenue is one of the top tourist attractions in Chicago and should be high on every sightseeing list of the area.
Is three days enough to stay in Chicago?
Three days in Chicago is enough to visit the city's key attractions. Many guests book for two days on average. Michigan Avenue, Navy Pier and Millennium Park are highly rated sights. Like to discover more? Stick around a little longer to visit nearby hotspots such as Rosemont.
Is Chicago a walkable city?
Some key attractions in Chicago, like Michigan Avenue and Navy Pier, are within walking distance. You can also experience several of the city's neighbourhoods on foot. Just 2 kilometres from central Chicago is Central Chicago and Near North Side is 2 kilometres away.
What are some activities to do in Chicago with kids?
Planning what to do in Chicago with kids has never been easier. Whether you're holidaying with teenagers or toddlers, there's a range of family-friendly attractions to keep them entertained here.

What to do in Chicago for adults?
McCormick Place and Wintrust Arena are just a couple of the things to do in Chicago. With plenty of activities available, there's something here for everyone to experience.
Are there free things to do in Chicago?
In Chicago, Michigan Avenue is an unmissable spot for anyone wishing to tour the city without taking their wallet out. Also, stroll around the green spaces and other neighbourhoods, and ask a local tour guide for ideas. It's a simple way to discover the best free things to do in Chicago.