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A view of the Chicago skyline pictured from Lincoln Park.

Things to do in  Chicago

Welcome to Chicago

Located along the shores of Lake Michigan, Chicago—the largest city in Illinois and the third largest in the United States—offers a wealth of art, music, historical, and architectural experiences. Culture lovers can stroll through Millennium Park and the Loop to view outdoor art (including the iconic “Bean”), tour world-class museums such as the Art Institute of Chicago, or cruise the Chicago River to see modern landmark gems. To meet the locals, buy a ticket for a ball game; catch some live blues or jazz (both of which have deep roots in Chicago) at a club; or laugh at the comedy acts at Second City, where many top comedians launched their careers.

Top 15 attractions in Chicago

Skydeck Chicago at Willis Tower (Sears Tower)

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Once the world’s tallest building, Willis Tower is still way up in the clouds. Though it functions as an office building, the skyscraper’s 103rd-floor Skydeck Chicago draws 1.7 million annual visitors for a trip out onto The Ledge, an enclosed glass balcony extending 4 feet (1.2 meters) out over the city, as well as panoramic views that—on clear days—extend as far as Indiana, Michigan, Iowa, and Wisconsin.More

The Magnificent Mile

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Fashion, architecture, and history in Chicago come together on this renowned stretch of Michigan Avenue nicknamed the Magnificent Mile. As you walk from the Chicago River to Oak Street, you’ll pass several Windy City landmarks, including the Water Tower, John Hancock Center, and Tribune Tower, as well as numerous luxury brand retailers.More

Chicago River

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Winding its way through the heart of the Windy City, the Chicago River flows past some of the city’s most notable architecture, including the Willis Tower (formerly the Sears Tower), Wrigley Building, and Navy Pier. The river also offers opportunities for exploration, such as river cruises, kayaking, and canoeing, along a revamped riverfront.More

Navy Pier

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Navy Pier is one of Chicago’s most popular tourist destinations—and with good reason. The 3,300-foot (1,010-meter) pier jutting into the waters of Lake Michigan, originally constructed in 1916 as a freight dock and public space, encompasses almost 50 acres (20 hectares) of exhibits, rides, parks, and family attractions.More

Chicago Riverwalk

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Connecting Lake Michigan to downtown, the Chicago Riverwalk is an open-air pedestrian-friendly walkway that runs along the Chicago River. Composed of six main sections, the Riverwalk is a main hub for entertainment. Head to the Marina Plaza section for restaurants, outdoor seating, and boat access. Take a stroll through a series of piers and floating wetland gardens at the Riverbank, or head to the Water Plaza where the kids can splash in water fountains.More

Millennium Park

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Located just a block away from Lake Michigan in the heart of downtown Chicago, Millennium Park showcases world-class art, music, architecture, and landscape design. Completed in 2004, the 24.5-acre (10-hectare) park is one of Chicago’s most popular destinations, drawing 25 million visitors per year.More

Chicago Cultural Center

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Opened in 1897 as Chicago’s first public library, the Chicago Cultural Center is the city’s hub for arts and cultural events as well as one of the city’s most beloved architectural monuments. The center is among Chicago’s most popular tourist attractions and features more than 1,000 free concerts, films, art exhibits, and other cultural events each year.More

Hard Rock Cafe Chicago

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The Hard Rock Cafe Chicago has been serving the Chicago River North area since its opening in 1986. River North borders the Magnificent Mile, is just across from the Loop, and a few blocks west of Michigan Avenue, a vibrant and popular dining and nightlife district.Be sure to order Hard Rock’s signature food offerings like the Legendary Burger and drinks like Rockarita. Check the menu for house made local entrees that have a touch of Chicago flavor as well.Like other Hard Rock Cafes around the world, the Hard Rock Cafe Chicago features music memorabilia on the walls, with an emphasis on funky styles. Be sure to tour the restaurant and see various guitars, platinum records, and more.There are numerous concerts and events taking place at the cafethroughout the year, so be sure to check the Hard Rock Cafe Chicago events page for details and reservations.More

Chicago Loop

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Chicago’s central business district, the Loop, is home to many of the city’s most recognizable landmarks, from museums and skyscrapers to parks and outdoor sculptures. Renowned for highlights like Grant Park, City Hall, and the Willis Tower, the Loop attracts both locals and visitors with its culture and entertainment offerings.More

Art Institute of Chicago

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Located in Chicago’s Grant Park, the Art Institute showcases 300,000 works of art ranging from ancient works to pieces created by today’s foremost artists. More than 1.5 million visitors from across the globe flock to the museum annually, making it one of Chicago’s most-visited destinations.More

Wrigley Building

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The 1920s were an important time for Chicago architecture, and when the Wrigley Building opened in 1925, it set the pace for the city’s development. When owner William Wrigley Jr. (of the Wrigley gum company) scouted locations for the building that would become his company’s headquarters, he chose a unique triangle shape of land that eventually became the bustling Magnificent Mile.More

360 Chicago Observation Deck (Formerly John Hancock Observatory)

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Formerly known as the John Hancock Observatory, 360 Chicago offers an interactive experience of the Windy City’s history and culture on the way up to its 94th-floor observation deck. From here, sweeping views of the Chicago skyline and Lake Michigan are enhanced by Tilt—moving glass lookouts that that literally tilt you out 1,000 feet (305 meters) above the Magnificent Mile.More

Grant Park

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Known as “Chicago’s Front Yard,” Grant Park stretches over 300 acres (121 hectares), and is the city’s primary downtown park. Located in the Loop, Grant Park is sandwiched between Lake Michigan and soaring skyscrapers. Its cultural highlights include the Art Institute of Chicago, the Museum Campus, and Millennium Park.More

Tribune Tower

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Once home to the Chicago Tribune, this neo-Gothic landmark was built as a result of the International Design Competition in 1922. Before this 462-foot (141-meter) building was constructed, reporters from the paper brought back pieces of rock from important landmarks around the world like the Taj Mahal, the Hagia Sophia, the Great Wall of China, and more.More

Chicago Theatre

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The historic Chicago Theatre, which dates back to 1921, is a popular downtown architectural landmark. With its famous dazzling marquee, French baroque architecture, and lobby modeled on a Versailles chapel, this picturesque structure today hosts concerts and comedy shows, as well as daily tours of its spectacular interior.More

Trip ideas

Top activities in Chicago

Chicago Architecture River Cruise
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Lake Michigan Sightseeing Cruise
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Lake Michigan Sightseeing Cruise

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Chicago Crime and Mob Bus Tour

Chicago Crime and Mob Bus Tour

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Chicago CityPASS

Chicago CityPASS

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90-Minute Chicago River Architecture Tour
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45-Minute Chicago River Architecture Tour from Magnificent Mile
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Chicago Craft Brewery Barrel Bus Tour
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Chicago in a Day: Food, History and Architecture Walking Tour
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Field Museum of Natural History Admission Tickets
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Underground Donut Tour: Chicago's First Donut Tour
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Chicago Premier Dinner Cruise on Lake Michigan
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Chicago City Minibus Tour

Chicago City Minibus Tour

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Operators have paid Viator more to have their experiences featured here

Recent reviews from experiences in Chicago

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Must do!
Adrienne_E, Nov 2022
Private Chicago Tour with Driver and tour Guide. Hotel pick up included
We learned so much and got to see all the sights!
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the tour was great we...
Sara_L, Nov 2022
90-Minute Chicago River Architecture Tour
the tour was great we were lucky the weather was nice we got to see the skyline of Chicago and enjoyed the history of the city the tour guide was really good making jokes and answer all the questions
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Worthwhile tour!
Jennifer_K, Nov 2022
Untouchable Tours Chicago's Original Gangster Tour
Also got to see many Chicago neighborhoods.
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To see all the buildings...
Jeffrey_O, Nov 2022
Chicago Architecture River Cruise
To see all the buildings and know all the history about Chicago was very interesting, even though it was freezing it was worth it to experience it.
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just amazing
REMINGTON_M, Nov 2022
90-Minute Chicago River Architecture Tour
was a very fun tour the tour guide Bobby made it that much more fun informative and really fun was all in all an amazing way to see an learn about chicago i plan to go again at night to see the city all lit up
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Close up views!
Tamara_D, Nov 2022
Big Bus Chicago Hop-On Hop-Off Tour
Excellent way to see Chicago!
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Beautiful Day on the River
William_L, Nov 2022
Chicago Architecture River Cruise
It’s a great way to see the city and learn about Chicago.
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Perfect 2 hour tour, lots of fun, especially on rainy day
Patrick_T, Nov 2022
Chicago Crime and Mob Bus Tour
Enjoyed this trip; a nice way to see the area of Chicago north of the river, with bonus views of the lakeshore.
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Most Awesome Tour of Chicago!!!!
Eric_B, Nov 2022
Chicago Small-Group City Tour with Optional Architecture River Cruise
pickup was on time and we got to see some of the best of Chicago and comical, informing commentary from our host.
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There is no better place...
Colin_M, Oct 2022
Lake Michigan Sightseeing Cruise
There is no better place to see the Chicago City Tall Skyscrapers than the Lake Michigan Boat Cruise.
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A must do if you’re in Chicago!
Shaun_C, Nov 2022
90-Minute Chicago River Architecture Tour
A great way to see a beautiful city.
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We took our kids to see...
Cassandra_K, Oct 2022
Gangsters and Ghosts Tour in Chicago
We took our kids to see Chicago and did this walking tour.
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Great experience
MJ_K, Oct 2022
Full-Day Small-Group Tour of Chicago Neighborhoods with Lunch and Dinner
I was born and raised in Chicago, but it was really fascinating to see how the city has changed since I left.
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Great overview of the city as seen from the river.
Cathleen_A, Nov 2022
90-Minute Chicago River Architecture Tour
Great way to see the city.
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Billy's 41st Birthday Surprise 🥳
Kiffany_G, Oct 2022
Helicopter Tour - Downtown Chicago
For my husband's 41st birthday he's not from Chicago so he was amazed to see it from above our favs of course was Riding over Lake Michigan 😎 An the view of Soldier Field from above.
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Great way to see downtown Chicago
Peter_B, Oct 2022
Big Bus Chicago Hop-On Hop-Off Tour
Enjoyed the convenience of being able to get off and back on at any of the attractions.
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Uplifting Chicago through urban art.
Constance_L, Oct 2022
Offbeat Street Art Tour of Chicago: Urban Graffiti, Art, and Murals
The spectacular mural in the park was beautiful aligning with the changing fall tree colors.
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Michael was a great tour...
Margo_K, Oct 2022
Chicago Crime and Mob Bus Tour
It was nice to be on a bus because we got to see quite a lot of the city.
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Beautiful Fall Day on a Boat ride
Mary_H, Oct 2022
Chicago Urban Adventure River and Lake Cruise
We had a beautiful fall day to take a boat ride down the river and along lake front.
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Chicago at it best!
Brenda_M, Nov 2022
Chicago Architecture River Cruise
A perfect way to see Chicago in a short amount of time.
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All about Chicago

When to visit

After being cooped up all winter, Chicago is ready to party when the sun comes out (sometime during May). Summer highlights include the annual Taste of Chicago, Chicago Blues Festival, Andersonville’s Midsommarfest, and the Chicago Air and Water Show. Alternatively, fall brings fewer crowds and brisker weather, perfect for exploring neighborhoods on foot and watching the trees turn colors along the quaint neighborhood streets.

Getting around

The Chicago Transit Authority (CTA) is your best friend when traveling around Chicago. You’ll see many references to “the Loop,” the circle elevated train tracks that define the city’s downtown area. From there, train lines (both underground and elevated) shoot out to the airport and the nearby suburbs. The CTA also has a robust network of bus lines that make all corners of the city easily accessible. The Loop itself is very walkable, and if you’re there in the dead of winter and your toes are frozen, hailing a cab is a cinch.

Traveler tips

The best place for a chargrilled Chicago hot dog after bar closing time (2am) is the Weiner’s Circle in Lincoln Park. The dog is served with a pickle, tomato wedges, chopped onions, sweet peppers, celery salt, and a side of major sass from the counterperson. If you know what’s good for you, never ever ask for ketchup—Chicago is a mustard town.

Currency
US Dollar ($)
Time Zone
CST (UTC -6)
Country Code
+1
Language(s)
English

A local’s pocket guide to Chicago

Claire Bullen

Born and raised in Chicago, Claire can claim city roots that go back at least three generations. The writer and editor currently calls London her home, but she's still a Chicagoan at heart.

The first thing you should do in Chicago is...

eat—after all, Chicago is a food lover’s paradise. While pizza and hot dogs are a starting point, you can find everything from top-notch Mexican food in Pilsen to exceptional dim sum in Chinatown and Michelin-starred fine-dining destinations around town.

A perfect Saturday in Chicago...

begins with brunch at Lula Cafe in Logan Square (definitely book ahead). After another coffee at Gaslight Coffee Roasters, go for a dose of culture at the Art Institute before cocktails at the Violet Hour ahead of a decadent dinner.

One touristy thing that lives up to the hype is...

the architectural boat tours, a genuinely great way to admire Chicago’s skyline and coast along the Chicago River. And don't forget deep-dish pizza—while many locals prefer tavern-style pizza, good deep-dish or stuffed pizza is special occasion-worthy.

To discover the "real" Chicago...

don’t just stay around the Loop. Chicago is a city of neighborhoods—from Chinatown to Hyde Park, Bronzeville to Humboldt Park, Lincoln Park to Wrigleyville — and the city’s real breadth and scope only come into focus when you leave downtown.

For the best view of the city...

The obvious choice is to head to the 360 CHICAGO Observation Deck in the Hancock Building or the Skydeck Chicago in the Willis Tower. But for fewer crowds, venture to Ping Tom Memorial Park in Chinatown for picture-perfect skyline views.

One thing people get wrong...

is assuming Chicago isn’t welcoming. Chicago combines big-city savvy and world-class cultural attractions with a real Midwestern warmth that comes through when you strike up a conversation with locals and listen to their stories.

People Also Ask

What is Chicago famous for?

Chicago is famous for its architecture—skyscrapers like the Willis Tower and John Hancock Center dominate its skyline, and architectural boat tours chart the Chicago River. The Windy City is also known for its signature bites like deep-dish pizza, its world-class museums, dynamic and diverse neighborhoods, and views overlooking Lake Michigan.

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How can I spend a day in Chicago?

If you have just one day in Chicago, start at the Skydeck Chicago at the Willis Tower for panoramic city views. Stroll through the Loop to Millennium Park and pose near "The Bean" before exploring the Art Institute of Chicago. Be sure to try Chicago's famous deep-dish pizza before leaving.

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How can I have fun in Chicago?

For a fun-filled day in Chicago, visit the attractions of Navy Pier, embark on a sightseeing boat tour of Lake Michigan, or head to the 360 Chicago Observation Deck for aerial views. Alternatively, go on a Segway tour of the Lakefront—and even see a Cubs game at Wrigley Field.

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What is the number 1 attraction in Chicago?

Chicago's number-one attraction is Millennium Park. This relaxing green space, steps from Lake Michigan, is home to many famous public artworks, including Anish Kapoor's "Cloud Gate"—better known as "The Bean." Right next door is the Art Institute of Chicago, where you can continue your cultural immersion indoors.

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What is there to do in Chicago in the winter?

Chicago is known for its snowy winters. For a winter-wonderland experience, discover the ice rink in Millennium Park or hit the Soldier Field Sledding Hill. Then, warm up in a top-rated museum, like the Art Institute of Chicago or Field Museum. End the evening with a musical or comedy show.

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