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 and a high-rise building as well as a family
Chicago which includes a city, signage and heritage elements
Lake Michigan showing city views, a river or creek and night scenes
Chicago which includes a skyscraper and street scenes as well as a family
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Most popular experiences in Chicago

Tours & day trips

See all 157 activities
Flyover in Chicago

Flyover in Chicago

Activity duration is 30 minutes
9.8 out of 10 with 13 reviews
Free cancellation available
Price is S$48 per adult
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Private & custom tours

See all 61 activities
Chicago Cocktail Adventure Part 1

Chicago Cocktail Adventure Part 1

Activity duration is 3 hours
Free cancellation available
Price is S$6 per adult
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Food, drink & nightlife

See all 26 activities
Chicago's Chinatown Food and Walking Tour

Chicago's Chinatown Food and Walking Tour

Activity duration is 3 hours
10.0 out of 10 with 263 reviews
Free cancellation available
Price is S$102 per adult
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Attractions

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360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

Activity duration is 30 minutes
8.6 out of 10 with 699 reviews
Free cancellation available
Price is S$37 per adult
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Classes & workshops

See all 16 activities
BYOB Spray Paint and Sip at Studio W.I.P.

BYOB Spray Paint and Sip at Studio W.I.P.

Activity duration is 1 hour and 30 minutes
9.8 out of 10 with 235 reviews
Free cancellation available
Price is S$57 per adult
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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
Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

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
McCormick Place showing a high rise building and a city

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
Navy Pier featuring a sunset and rides

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
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
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
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
Grant Park showing a garden and night scenes

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_UnitedCenter_6064077_01

United Center

4.5/5(15 reviews)

Catch an event at United Center during your trip to Chicago. Amble around this vibrant area's lakeside or experience its entertainment choices.

United Center

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
River North showing railway items, street scenes and a city

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
Underground passage in the Chicago O'Hare airport

O'Hare

3.5/5(10 area reviews)

Travellers choose O'Hare for its abundant dining options. Hop aboard the metro at Cumberland Station or Remote Parking Station and check out top sights like Fashion Outlets of Chicago.

O'Hare
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

 

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

Kishwaukee River in Northern Illinois

Buffalo Grove

Reflection on Lake at Dusk at Turtlehead Lake Nature Preserve in Orland Park, IL (Suburban Chicago)

Crestwood

Rosemont

Rosemont

sunrise at Busse Lake Elk Grove Village, Illinois USA

Elk Grove Village

Schaumburg showing farmland as well as an individual female

Schaumburg

Lilacia Park

Lombard

Ultra-wide panorama of Turner Lake and native prairie grasses and trees in autumn at Moraine Hills State Park in McHenry County, Illinois

Libertyville

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.

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