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Things to do in Chicago

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.

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.

Top 10 attractions in Chicago

#1
Navy Pier

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
#2
Skydeck Chicago at Willis Tower (Sears Tower)

Skydeck Chicago at Willis Tower (Sears Tower)

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Once the world’s tallest building when it opened in 1973 as Sears Tower, Willis Tower is still way up in the clouds. The 1,454-foot (443-meter) skyscraper reigns as the third tallest building in all of North America with its spires just 325 feet (99 meters) shorter than Manhattan’s One World Trade Center. Though it functions as an office tower, 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 four feet (1.2 meters) outside the 103rd floor, and for panoramic views that, on clear days, extend as far as Indiana, Michigan, Iowa, and Wisconsin.More
#3
Marina City

Marina City

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The dueling main columns of Marina City overlook the Chicago River. Its scalloped “corn-on-the-cob” exterior, formed by undulating half-moon balconies, has made it instantly recognizable and a popular setting in movies such as Batman Begins, Ferris Bueller’s Day Off, and The Blues Brothers. While the historic buildings are largely residential—some 1,400 people call Marina City home today—visitors are welcome to the complex. You can head up to roof decks for 360 degree views of the city skyline, rent boats in the attached marina to explore the Chicago river, dine in restaurants like Smith and Wollensky’s Grill, catch a concert in the House of Blues, and even use the structures’ ice skating rink, swimming pool, and bowling alley.Marina City’s 588-foot towers, designed by great Chicago architect Bertrand Goldberg, were the tallest residential structures and the tallest concrete buildings in the world when they were constructed in the early 1960s. Forty-stories of pie-shaped apartments, designed to emphasize city views, sit atop twenty stories of parking. Designed as a “city within a city,” with shopping, dining, office buildings, recreational spaces, and entertainment for its residents, the then-novel concept was part of a movement encouraging Chicagoans to return to downtown from the suburbs.More
#4
Millennium Park

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
#5
Chicago River

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
#6
Chicago Riverwalk

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
#7
Wrigley Building

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
#8
Grant Park

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
#9
The Magnificent Mile

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
#10
Chicago Cultural Center

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

Trip ideas

Don’t-Miss Dishes in Chicago

Don’t-Miss Dishes in Chicago

Recent reviews from experiences in Chicago

star-5
A must if you're new in Chicago!
Katherine_C, Dec 2020
Chicago Architecture River Cruise
The views are impressive and the history behind the buildings you get to see is really enjoyable, Recommended for those who like history, architecture and photography.
star-4
Great Skyline
David_O, Nov 2020
Chicago Architecture River Cruise
And dress warmly if’ not in summer
star-5
Beautiful
David_E, Nov 2020
Chicago Lake and River Architecture Tour
If you want to see the beauty of Chicago I recommend you see it from the river view.
star-5
Fun evening activity
Tyler_G, Oct 2020
Gangsters and Ghosts Tour in Chicago
Really informational tour, gave us a good insight into the history and interesting facts about Chicago that we didn't hear about during other activities that we did their during our visit.
star-5
Good Times!
Emily, Oct 2020
Bikes, Bites, and Brews: Chicago's Signature Dishes Bike Tour
The bike ride portion was way easier than expected and we got to see so much of the city.
star-5
Easy Chicago Touring
Keith_M, Oct 2020
Chicago CityPASS
This is the easiest and most cost effective way to see multiple Chicago attractions.
star-5
Awesome time
Rodney_J, Nov 2020
Chicago Architecture River Cruise
It was very enjoyable to see the different buildings and learn some history
star-5
A must
Visitor, Oct 2020
90-Minute Chicago River Architecture Tour
Fun way to see Chicago’s incredible architecture.
star-5
Super - will recommend
Marci, Sep 2020
Gangsters and Ghosts Tour in Chicago
Lastly, walking around the beautiful Chicago downtown on a late summer night - what could be better?!
star-5
Great evening!
Allie, Feb 2021
Traveling Spoon Chicago-Style Deep Dish Pizza Private Online Cooking Class
My boyfriend and I (who are missing Illinois, having been unable to visit for over a year now) had a great evening making Chicago-style pizza with Nancy!
star-5
Great Use of Four Hours!
Shawnte, Sep 2020
Bikes, Bites, and Brews: Chicago's Signature Dishes Bike Tour
This is probably obvious, but worth noting is that this tour is in non-congested locations, which is great, but if you are expecting to see city landmarks, you will need to supplement this tour with another.
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Awesome
Clare_L, Aug 2020
90-Minute Chicago River Architecture Tour
A fun and unique way to see the city of Chicago and learn its history.
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Nice for calm evening cruise
Atcope, Oct 2020
Chicago Architecture River Cruise
I just decided to try at last minute for my last days off of fall, and enjoyed as a beginner just has been interested in architecture to take an advantage moved in Chicago.
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Totally Worth it.
niazikhan, Jan 2020
Chicago in a Day: Food, History and Architecture Combo Tour
He showed us some wonderful places in Chicago and made me fall in love with the city's architecture.
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Good Activity for an Overcast Day8
6243310, Nov 2019
Chicago City Minibus Tour with Optional Architecture River Cruise
Tour was a great way to see Chicago neighborhoods and important architectural sites on a drizzly day.
star-5
Awesome sights great views
Dawn M, Oct 2019
Big Bus Chicago Hop-On Hop-Off Tour
Would highly recommend to anyone who wants to see a little bit in a short time.
star-5
Entertaining and informative
Joseph_D, Sep 2020
Gangsters and Ghosts Tour in Chicago
Not being from Chicago, it was a nice (and entertaining) way to see some of downtown.
star-5
Excellent Pass to see Chicago
Randy G, Oct 2019
Chicago CityPASS
The Chicago CityPASS was an excellent way to see some of the best museums and landmarks for the city.
star-5
Big Bus tour
306Martha123, Sep 2019
Big Bus Chicago Hop-On Hop-Off Tour
Chicago is a beautiful city and there is no better way to see it than through this hop on bus company.
star-5
Definitely a Bucket List Add On
idw87, Sep 2019
Chicago River Floating Tiki Bar Cruise
Great for out of town guests to see Chicago’s beautiful architecture along the Chicago River.

Frequently Asked Questions

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