What to do in Chicago, IL

Activities, attractions and tours

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

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$9, 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 175 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.

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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.
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Wrigley Field showing a city and landscape views

2. 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.
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McCormick Place showing a high rise building and a city

3. 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.
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Navy Pier featuring a sunset and rides

4. 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.
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Reflection of a Chicago buildings in a mirror of Chicago Bean, Millennium Park, Chicago city, USA., Shutterstock ID 1129809965, Purchase Order: SP-2109, Order Number: SP-2109 Qantas AU US Sale New Ads

5. 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.
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Soldier Field showing a city and landscape views

6. 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.
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Chicago Riverwalk showing a city, a river or creek and a ferry

7. 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.
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Grant Park showing landscape views, a park and a city

Recommended things to do in Chicago

Number of things to do
175
Cheapest thing to do on Expedia
A Storied Area: A Self-Guided Audio Tour with Bill Ayers: NZ$9
Top 5 things to do
Half-day tours
With kids

What to do in Chicago

Discover the most popular places to visit in Chicago

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

5/5(5 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
Wrigley Field which includes a city, central business district and a sporting event

Wrigley Field

4.5/5(21 reviews)

A big piece of Chicago's soul, an ancient stadium that keeps alive the quirky, edgy madness of baseball.

Wrigley Field
McCormick Place showing a high rise building and a city

McCormick Place

4.5/5(21 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

4.5/5(64 reviews)

One of Chicago’s most popular attractions, especially on a hot day, with its fun fair, boats, circus and theatre.

Navy Pier
Millennium Park showing modern architecture, a city and street scenes

Millennium Park

4.5/5(73 reviews)

See mind-bending sculptures, a musically-inspired lawn and giant water fountains that double-up as video screens.

Millennium Park
Soldier Field featuring a city, modern architecture and a high-rise building

Soldier Field

4/5(13 reviews)

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

Soldier Field
Chicago Riverwalk featuring a bay or harbour, a city and a river or creek

Chicago Riverwalk

4.5/5(26 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
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United Center

5/5(8 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
Grant Park showing a garden and night scenes

Grant Park

4.5/5(47 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

Explore areas of Chicago

Downtown Chicago featuring 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

An avenue brimming with superb shops and restaurants, the Magnificent Mile more than lives up to its name.

Magnificent Mile
The Loop - Downtown which includes a river or creek

The Loop

4.5/5(93 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
The dinosaur is ready for American football season.

O'Hare

3.5/5(9 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
Beautiful fireworks

Theatre District

While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more of the city at Washington Station or Monroe Station (Blue Line).

Theatre District

 

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

Aurora which includes a city and a river or creek

Aurora

It's fun to watch and bet on the horses

Arlington Heights

I like the architecture of this airport. I always find myself snapping pics at O'Hare

Schiller Park

Authentic polish smorgasbord. They have ghost tours followed by a meal, too.

Broadview

Rosemont

Rosemont

The beginning of fall

Elk Grove Village

Prairie Lakes Park in Des Plaines Town of Illinois

Des Plaines

Grosse Point Lighthouse featuring a lighthouse and a house

Evanston

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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