16 Must-See Attractions In Chicago

There are endless things to do in Chicago, Illinois, from exploring museums and galleries like the Art Institute of Chicago to playing tourist in Millennium Park to gorging on deep-dish pizza. The birthplace of the modern skyscraper also boasts an impressive skyline, which towers over the Magnificent Mile shopping stretch and Lake Michigan’s urban beaches. Lace up those walking shoes for a show-stopping tour of these top Chicago attractions.

1. The Art Institute of Chicago, for brushing up on art history

Art Gallery

This Chicago attraction is the crown jewel in the city’s cultural scene. The museum has more than 300,000 works in its permanent collection, spanning movements from the Renaissance to Surrealism, and a stellar roster of rotating exhibitions. Expect to see quintessential pieces by Edward Hopper, van Gogh, Picasso, Monet and Cézanne, plus a vast array of sculptures, ceramics and contemporary pieces. Book a fast-pass ticket before arriving to skip the line.

2. Skydeck Chicago, Willis Tower, for vertigo-inducing views

Building

Willis Tower Skydeck, Chicago, United States

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You’ll need a head for heights to ride to the top of the hulk of steel that is the Willis Tower. Standing at 1,450ft (442m), it is the tallest building in Chicago. Luckily, no physical exertion is required, as a 70-second elevator whizzes you to the 103rd-floor Skydeck. You’ll need to be strong in other ways to join the brave tourists posing on glass-enclosed ledges that jut out over the city streets below – an iconic Chicago attraction.

3. The Bean, for getting reflective

Architectural Landmark

The Bean, Cloud Gate, Chicago, United States

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Inspired by liquid mercury, this most recognizable of Chicago attractions is actually named Cloud Gate and is one of the best things you can do in Chicago for free. Adding shine to the lakefront Millennium Park, the surface of the colossal stainless steel bean by artist Anish Kapoor reflects the park, the sky and tourists who love to take a selfie here – don’t worry, cleaners buff up the exterior several times a day to remove all the sticky fingerprints. In the summer, take a relaxing stroll through the Lurie Garden, and enjoy picnics and open-air concerts in the pavilion. In the winter, go ice skating at the McCormick Tribune Ice Rink.

4. Navy Pier, for thrills ‘n’ spills

Memorial

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Jutting into Lake Michigan, this temple of fun is packed with Chicago attractions for kids and adults alike. Take in the view from the top of the whirring Ferris wheel, catch a movie at the IMAX, watch a production at Chicago Shakespeare Theater or quench your thirst in the beer garden. The Chicago Children’s Museum will hold the attention of the most fidgety little ones with hands-on exhibitions like the Dinosaur Expedition.

5. The Second City, for comedy club laughs

Theater

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The home of improv and the heart of the US comedy scene, the Second City Chicago has been a pioneering hilarity hub for over 50 years. With its very own special sauce of weird and wonderful Chicago-style sketch and improv comedy running every night of the week, there’s plenty of variety to keep you coming back for more. Book tickets online, as they can sell out fast.

6. Fat Johnnie's Hot Dogs, for classic street food

Architectural Landmark

Street Food Tours

Hot dogs are as much a part of Chicago as skyscrapers. Selling his own version from a ramshackle stand on Western Avenue for over 40 years, the eponymous Johnnie was the first to put a hot dog and a corn tamale in one bun, but it’s the Red Hot chili-topped hot dog that’s the star of the show. With no tables or chairs, you’ll need to eat on the sidewalk or at a nearby bench or save the joy for your hotel room (we bet you don’t).

7. Bike, run or walk the Lakefront Path

Natural Feature

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Chicago’s 18-mile (29km) lakefront path spans the entire east side of the city. It’s a picturesque place to spend a sunny day walking, biking or running beside beautiful Lake Michigan while also seeing gorgeous views of the Chicago skyline. Along the way, you’ll pass dozens of free parks and public beaches where you can take a rest, play some catch or go for a swim. The path recently underwent a massive expansion. Now, bikers and pedestrians use separate lanes, making it safer and more enjoyable for everyone. Recommended by Molly Sprayregen

8. Take the Chicago Architecture Center’s river cruise

Natural Feature, Architectural Landmark

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Hop aboard this boat cruise and spend time winding down the Chicago River while learning stories behind the fascinating architecture you see along the way. Chicago’s architecture is truly one-of-a-kind, and this fascinating tour is beloved by locals and tourists alike. If you’re interested in taking a cruise but architecture isn’t your thing, try a cocktail cruise or a sunset cruise, or one with live music. This city is interesting whether you see it late at night or early in the morning. Recommended by Molly Sprayregen

9. Explore the Riverwalk

Park, Architectural Landmark

River flowing through sky scrapers, Chicago riverwalk

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Along the most central part of the Chicago River, running right through downtown, is a pedestrian walkway stretching just over a mile (1.6km). It’s a lovely place for a stroll and offers a taste of nature in the city. There are any number of attractive waterside restaurants and bars to drop into while you’re there, or you could try renting a kayak to see the river from a different perspective. There are also lots of areas to simply sit back, relax and watch the boats drift by.

10. Attend a Cubs game at the Wrigley Field

Sports Center, Stadium

Wrigley Field (via Eisenhower), Chicago, United States

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As the second-oldest ballpark in Major League Baseball, Wrigley Field is more than worth an afternoon visit. Take in a game during the Cubs’ wildly successful season or go on an after-hours tour behind the scenes to soak in the park’s grandeur. Recommended by Elizabeth Newhart

11. Chicago Pizza and Oven Grinder Company, for pizza pot pie

Pizzeria

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Chicago is known for its deep-dish pizza, but this spot takes things to the next level with its pizza pot pie: a doughy bowl of melted cheese and tomato flipped tableside by your server. Located in the Lincoln Park neighborhood, the restaurant sits across the street from the site of the infamous St. Valentine’s Day Massacre, where Al Capone’s henchmen murdered seven rival gang members.

Garfield Park Conservatory, for a tropical escape

One of the country’s biggest conservatories, this epic botanical experience nestled in Garfield Park is home to a vast collection of plants from around the world. Explore the Palm House, Fern Room and Desert House before venturing outdoors to the gardens – if you’re looking for Chicago things to do with kids, seek out the children’s garden. Alongside the permanent display houses, seasonal dynamic exhibits and installations from local artists and community members are abundant. With no admission charge, this is one of the top Chicago things to do for free.

North Avenue Beach, for water sports

Chicago and beaches? We’re serious! Despite the sea of skyscrapers, the presence of Lake Michigan means 26 official sandy spots are within easy reach of the city. Ignore the weather, as the water is pretty icy year-round. Near Lincoln Park, North Avenue Beach is always buzzing and has plenty of places to rent kayaks and paddle boards, so you can be on the water – not in it. At the very least, take a waterside walk or rent a bicycle.

The DuSable Museum of African American History, for celebrating Black culture

Affiliated with the Smithsonian Institution, this was the first independent museum of Black history, culture and art in the United States when it opened in 1961. Founded by American visual artist and writer Margaret Taylor-Burroughs in her own home, the leafy Hyde Park site now holds 15,000 pieces, including paintings, sculptures, print works and historical memorabilia, and hosts regular workshops and discussions.

The Green Mill, for reveling in jazz history

Open since 1907, this Chicago institution has a rich history as a mobster hangout, a Prohibition-era speakeasy and a stage for some of the biggest names in jazz. These days, you can catch live music nightly from its time-worn booths. Do bring cash, but don’t ask to take a tour of the tunnels that Al Capone was rumored to escape through when trouble hit.

The Walnut Room, for dining on Midwestern classics

Despite the steely skyscrapers, there’s an old-school feel to Chicago you can mine unapologetically at the Walnut Room. Cocooned in wood paneling and chandeliers on the seventh floor of Macy’s on State Street, it serves traditional Midwestern staples like Mrs. Hering’s chicken pot pie and classic meatloaf, made using the same recipe as when the restaurant opened in 1905. Visiting at Christmas? Book well in advance to experience this holiday season favorite decked to the nines.

Find the awesome places to stay in the Windy City with our guide to the best boutique hotels in Chicago, the best hotels near Lake Michigan and the best hotels in the Loop, Chicago, all bookable with Culture Trip.

Tara Gardner contributed additional reporting to this article.