What to do in Chicago, IL

Activities, attractions and tours

A city skyline with modern skyscrapers and a river with boats and people in the foreground.
The Adler School's 2012 Commencement Ceremony at the Chicago Theatre.
A nighttime cityscape with illuminated skyscrapers and a river.
A modern building with a glass facade and a Ferris wheel in the background.
A cityscape with tall buildings partially obscured by clouds.

Places to Visit in Chicago

Ready for the adventure of a lifetime? Let Expedia.co.nz help you find the most exciting and fun things to do in Chicago, Illinois while also allowing you to save a ton on travel arrangements. Regardless of whether you’re an urban explorer or an intrepid outdoor enthusiast, we can help you decide exactly what to do and see during your time in town.

Our thorough travel guides offer you an insider’s perspective on all of the best Chicago attractions from NZ$2, making it easy for you to decide which places to visit and when. And by using Expedia.co.nz to set your sightseeing schedule, you can take in more of the enchanting attractions this area is famous for.

From group Chicago tours and must-see landmarks to personal guides who take you off-the-beaten track, Expedia.co.nz offers you over 358 of the most popular events, activities, and attractions in this corner of the world. So whether you’re travelling alone, alongside a loved one, or with the whole family in tow, be sure to browse through our extensive travel guides prior to your plane touching down in this spectacular Chicago. We even have a massive selection of flights, car hires, and accommodation for you to choose from. So what are you waiting for? Start your search today, and you’ll be having the time of your life before you know it.

Activities

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

NZ$47
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

NZ$42
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Art Institute of Chicago

Art Institute of Chicago

NZ$69
per adult
92% of travellers recommend
Art Institute of Chicago
Flyover in Chicago

Flyover in Chicago

NZ$54
per adult
96% of travellers recommend
Flyover in Chicago
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

NZ$70
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Chicago C3® : Save on admission to your choice of 3 top attractactions

Chicago C3® by CityPASS®

NZ$189
per adult
88% of travellers recommend
Chicago C3® by CityPASS®
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

NZ$80
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
See all activities in Chicago
  • find price illustration

    Explore activities

    Explore thousands of experiences from activities and attractions to day tours and transfer.
  • calendar shield illustration

    Book with ease

    Skip the line- book tickets online in minutes to top attractions with free cancellation on many activities.
  • trophy illustration

    Treat yourself

    Members save % or more when you book activities.

Top places to visit

1. Wrigley Field

For sports-fans, Chicago is about one of two things – the Bears or the Cubs. But while the Chicago Bears football team switched from Wrigley Park in 1971, its legendary baseball team, the Chicago Cubs, have stuck true to their long heritage here. They've stayed put at one of America's most iconic sports fields, ever since it was built in 1914. After all, Wrigley Park has legendary sporting triumphs (and disasters) steeped into every seat, and written on every leaf of its ivy-covered outfield walls.
Learn more
An aerial view of a baseball stadium surrounded by urban buildings.

2. Navy Pier

Navy Pier has been many things to Chicago, since it first struck out its 1006 metres into Lake Michigan in 1916. It was once a transport hub, a navy training centre, and even a place for the city to cool down in the days before air-conditioning. Now it’s the capital of fun for Chicagoans, home to circuses, fun fairs, fireworks and flower shows. It's one of the city's most popular attractions when summer arrives, and its twice-weekly firework shows begin. It's also a great launching off point for getting all nautical along Lake Michigan's 483-kilometre length.
Learn more
A Ferris wheel and a carousel at a fairground.

3. Soldier Field

Soldier Field has been one of Chicago’s most well-known landmarks since its construction in 1924 and is the oldest NFL stadium in the country.
Learn more
A large stadium surrounded by a cityscape with modern buildings.

4. Chicago Riverwalk

Get a sense of the culture and character of the Windy City by wandering along the Chicago Riverwalk. This scenic stretch of the city follows the banks of the Chicago River from near the edge of Lake Michigan through Downtown to where the river splits. As you follow the walkway, pass impressive bridges, fascinating museums and trendy dining spots.
Learn more
A river with boats, surrounded by tall buildings and a clear sky.

5. McCormick Place

McCormick Place is both the biggest convention center in Chicago and the biggest one anywhere in the U.S. This vast, sprawling complex is an impressive feat of architecture and engineering that was founded well over half a century ago. Attend an event here to get a sense of its incredible scale.
Learn more
A modern cityscape with tall buildings, a clear sky, and a tree-lined street.

6. Millennium Park

You may know Chicago as the Windy City. But its motto is actually Urbs in Horto - or 'City in a Garden.' And parks, large and small, abound in this surprisingly spacious city on Lake Michigan's shore. But none is quite like the Millennium Park, which was added to Chicago's long park list just this side of the new millennium (2004 to be exact – punctuality isn't big with Chicagoans). Less a park, more a 'new kind of town square', Millennium Park is a very 21st-century blend of art, open-spaces, dramatic vistas and engrossing events.
Learn more
A cityscape with modern skyscrapers and the Cloud Gate sculpture.

7. Six Flags Great America

Locals and visitors come to Six Flags Great America to escape the heat during Milwaukee’s summer months. The theme park has almost 7 miles (11 kilometers) of roller coaster track alongside a host of other family attractions and entertainment set over a sprawling area close to the Wisconsin–Illinois state line.
Learn more
A roller coaster in motion against a clear blue sky.

8. Grant Park

Grant Park is one of Chicago’s most loved and diverse public parks, with a host of family-friendly attractions and activities. It spreads across 319 acres (129 hectares) between Michigan Avenue and the banks of Lake Michigan. Grant Park is a scenic area blessed with everything from concert venues and museums to public art, statues and well-groomed lawns. Walk along wide tree-lined promenades dissecting the park.
Learn more
A park with walking paths, trees, and benches. In the background, there are tall buildings, including a prominent skyscraper.

What to do in Chicago

Stay near popular Chicago attractions

An aerial view of a baseball stadium surrounded by urban buildings.
Photo by © City of Chicago
Open Photo by © City of Chicago

Wrigley Field

9.0/10 (11,704 reviews)
Step into baseball's living museum where ivy-covered walls and a hand-operated scoreboard create timeless charm. Experience the electrifying atmosphere of Cubs games in this century-old "Friendly Confines."
See properties

Our guide on where to stay in Chicago

Find the best Chicago areas for the activities you enjoy most. Learn more about Chicago
Learn more about Chicago
A river with yellow boats, a bridge, and tall buildings.

The Loop

Michigan Avenue and Lake Michigan are a few top attractions in The Loop. Hop around the city on the metro at Washington Station or Lake Station and check out the area's fascinating museums, popular shops and acclaimed art galleries.

A city street with a train passing overhead, cars, pedestrians, and a red brick building.

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.

A historic castle-like building with intricate stonework and a paved walkway.

Magnificent Mile

Are you interested in fascinating museums, panoramic lake views and popular shops? A visit to Magnificent Mile might be the perfect thing. You can also explore top sights like Michigan Avenue and Chicago Water Tower.

A cityscape with modern skyscrapers and a curved highway.

West Loop

Consider a visit to Milwaukee Avenue and take some time to enjoy the abundant dining options during your time in West Loop. If you want to see more of the city, jump on the metro at Racine Station or Ogilvie Transportation Center.

A river with a city skyline in the background, surrounded by green trees and grass.

Lincoln Park

Known for its ample dining options and fantastic lake views, there's plenty to explore in Lincoln Park. You can visit top attractions like Lake Michigan and Lincoln Hall, and jump on the metro at Fullerton Station or Armitage Station to see more of the city.

 

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.

 

 

Day trip destinations from Chicago

A cityscape with a bridge over a river, a historic building with arches, and modern high-rise buildings.

Aurora

A serene garden with a pond, neatly trimmed bushes, and a stone bridge.

Arlington Heights

A frozen river with ducks, snow-covered trees, and a clear sky.

Burr Ridge

A park with picnic tables, a gazebo, playground equipment, and a large tree.

Vernon Hills

A hilly landscape with a person walking on a path, surrounded by trees and grass.

Rolling Meadows

A city skyline with modern skyscrapers, a marina with boats, and a coastal park.

Schiller Park

A neon sign for Old Warsaw Polish Style Smorgasbord.

Broadview

A modern building with a glass facade and a large tree in front.

Rosemont

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.

Explore a world of travel with Expedia