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The Bean
Photograph: Neal O'Bryan

The 24 best Chicago attractions

The best Chicago attractions include vast city parks, intriguing museums, soaring skyscrapers and sightseeing venues

By Zach Long and Morgan Olsen

It’s no surprise that Chicago is one of the finest tourist destinations in the country. There are miles of beautiful Chicago beaches, Chicago museums that rank among the world's best and the friendliest city-dwellers out there (if we do say so ourselves). With so much to see and do, it can be tough for visitors to decide which Chicago attractions are really worth experiencing. Whether you’re an out-of-towner or a tried-and-true Chicagoan planning a staycation, we’ve assembled the 25 best Chicago attractions for your touring convenience. Oh, and if you’re feeling decadent, cap off your day of sightseeing with a meal at one of the best restaurants in Chicago. Ready to dive in to the windy city? Here are the Chicago attractions you simply shouldn't miss.

Best of the city under one roof

Time Out Market Chicago Atmosphere
Jack Li

Time Out Market Chicago

We've rounded up the best chefs in the city to join us at Time Out Market Chicago, a culinary and cultural destination in the heart of Fulton Market. The 50,000-square-foot space houses 18 kitchens, three bars and one drop-dead gorgeous rooftop terrace—all spread across three floors.

The mission behind Time Out Market Chicago is simple: Our local editors taste their way through town, and if we discover something that’s great, it goes in our magazine and all of our coverage; if it’s unmissable, it also goes in Time Out Market Chicago. It's so much more than the F-word (food hall); it's a culinary and cultural epicenter that's packed with amazing things to eat, drink and do. Where else can you eat a slice from Art of Pizza, pop dumplings from Bill Kim, wash it all down with a Malört cocktail and then take an art class?

Best Chicago attractions

Millennium Park
Photograph: Neal O'Bryan

1. Millennium Park

Attractions Parks and gardens Millennium Park

What is it? This vast 24.5-acre section of Chicago’s front yard is one of the most popular places to spend time outdoors in the city, look at public art and attend special events.

Why go? To take a selfie in front of Cloud Gate (a.k.a. the Bean), go for a stroll through the serene Lurie Gardens, catch a free concert in the Frank Gehry-designed Jay Pritzker Pavilion (in the summer) or skate on the McCormick Tribune Ice Rink (in the winter).

2. Art Institute of Chicago

Museums Art and design Grant Park

What is it? One of the city’s most well-known cultural institutions, which houses more than 300,000 artworks and an on-site restaurant, Terzo Piano (Italian-Mediterranean food).

Why go? Acquaint yourself with classic paintings like Georges Seurat’s A Sunday on La Grande Jatte (as seen in Ferris Bueller’s Day Off) and Grant Wood's American Gothic, or explore an expansive collection of contemporary works in the museum’s Modern Wing. Check the museum's website for more information on temporary exhibitions.

Zoo animals
Photograph: Nicola Dreyer on Unsplash

3. Lincoln Park Zoo

Things to do Lincoln Park

What is it? Located in the middle of Lincoln Park, this 35-acre zoo houses more than 1,000 animals and is one of the few remaining free zoos in the country.

Why go? Watch cute African penguins frolicking in Penguin Cove, observe majestic cats in the Kovler Lion House or visit the scaled residents of the McCormick Reptile House—all entirely free of charge. Trust us, it’ll get wild.

4. Garfield Park Conservatory

Attractions Parks and gardens East Garfield Park

What is it? Among the largest conservatories in the United States, this giant greenhouse in Garfield Park provides a home for some 600 species of plants (most of which aren’t indigenous to the region).

Why go? Stop by 365 days a year to admire the gigantic trees that fill the Palm Room, see a depiction of ancient Illinois vegetation in the Fern Room or window shop for succulents and cacti in the Desert Room.

Photograph: Neal O'Bryan

5. Wrigley Field

Sports and fitness Baseball & softball Wrigleyville

What is it? Built in 1914, Wrigley Field has been the home of North Side baseball team the Chicago Cubs for more than 100 years.

Why go? To watch baseball at one of the oldest ballparks in America, sing along during the seventh-inning stretch and see one of the only manually operated scoreboards in existence, controlled by three members of the Cubs staff.

Photograph: Callie Lipkin Photography, Inc.

6. Museum of Contemporary Art

Museums Art and design Streeterville

What is it? Hosting one of the largest collections of contemporary art in the United States, this Chicago museum is a destination for cutting edge exhibitions and programming.

Why go? Take in a constantly changing lineup of exhibitions, including touring shows from the likes of Takashi Murakami and Kerry James Marshall, or stop by the museum’s in-house restaurant, Marisol, where chef Lula Cafe chef Jason Hammel serves an inventive menu.


7. The Second City

Comedy Comedy clubs Lincoln Park

What is it? Bill Murray, Tina Fey, Stephen Colbert and Joan Rivers are just a few of the famous folks who honed their talents onstage at this theater devoted to sketch and improvised comedy.

Why go? You’ll see some of the most talented rising comedic talents (and maybe a couple future Saturday Night Live cast members) on the Second City’s Mainstage. If you want to learn more about improv, stand-up or sketch writing, you can sign up for a class at the Training Center.

Turning Sky
Photograph: Neal O'Bryan

8. The 606

Attractions Parks and gardens Humboldt Park

What is it? A 2.7-mile stretch of an abandoned elevated rail line that has been transformed into a pedestrian path that connects Logan Square, Humboldt Park, Bucktown and Wicker Park.

Why go? It’s a great place to go for a jog, zip around on your bicycle and quickly transverse some of the most popular North Side neighborhoods. Plus, you’ll spot some art installations as you go.

Photograph: Martha Williams

9. The Green Mill

Bars Cocktail bars Uptown

What is it? This Uptown cocktail lounge is a fixture of Chicago’s live jazz scene and has been slinging drinks since before Prohibition (Al Capone and other gangsters used to hang out at the Green Mill).

Why go? Once you’ve snapped a picture of the iconic Green Mill marquee, head inside, order a cocktail and take in a set from some of the city’s top jazz musicians. The music typically goes late, but you’ll need to show up early if you want to score a good seat.

Photograph: Grace DuVal

10. The Field Museum

Museums Science and technology Museum Campus

What is it? Founded to house the biological and anthropological collections assembled for the World’s Columbian Exposition of 1893, this massive natural history museum has more dinosaur bones and ancient artifacts than any other institution in Chicago.

Why go? Travel back in time by descending into a recreation of an ancient Egyptian tomb, stand beneath a towering titanosaur skeleton or stare at sparkling stones in the Grainger Hall of Gems.

Chicago Riverwalk
Photograph: Jaclyn Rivas

11. Chicago Riverwalk

Things to do Loop

What is it? Hugging the banks of the main branch of the Chicago River, the Riverwalk provides a pedestrian path along the city’s most popular waterway, lined with restaurants, bars and gathering spaces.

Why go? The waterside walkway allows you to observe some of the city’s most gorgeous architecture from a new perspective. You can also sip a glass of merlot at City Winery, take in the Art on theMart projections on the side of Merchandise Mart or board a Water Taxi for a leisurely trip to Chinatown.

Shedd Aquarium
Photograph: Neal O'Bryan

12. Shedd Aquarium

Attractions Zoo and aquariums Museum Campus

What is it? This Museum Campus staple is the home to thousands of aquatic creatures from all around the world, including adorable otters and a giant Pacific octopus.

Why go? Watch tropical fish swim through a 90,000-gallon aquarium in the gigantic Caribbean Reef exhibition or pony up some extra cash to have a face-to-face encounter with a beluga whale.

Museum of Science and Industry
Photograph: J.B. Spector

13. Museum of Science and Industry

Museums Science and technology Hyde Park

What is it? Interactivity is the name of the game at the Museum of Science and Industry, a Hyde Park institution that boasts a mirror maze, a simulated tornado and a WWII-era U-505 German on display.

Why go? Step inside a building that dates back to the World’s Columbian Exposition of 1893 and explore exhibits that depict a Chicago street circa 1910 and a massive model railroad that depicts the 2,200-mile journey from Seattle to Chicago.

Nick Cave at Chicago Theatre | March 31, 2013
Photograph: Josh Mellin

14. Chicago Theatre

Music Music venues Loop

What is it? A 3,600-seat theater that was established in the 1920s as a movie palace. There days, you're more likely to see for concerts, comedians and dance performances in the venue.

Why go? Find a spot on the sidewalk to snap a photo in front of the Chicago Theatre's iconic marquee, take a tour of the venue (which includes a chance to stand on stage and peek inside the dressing rooms) or catch a set from acts like Wilco, John Mulaney and Madonna.

National Museum of Mexican Art
Photograph: Jaclyn Rivas

15. National Museum of Mexican Art

Museums Art and design Lower West Side

What is it? Located in the traditionally Hispanic neighborhood of Pilsen, this cultural institution hosts one of the country’s largest collection of Mexican art—and admission is always free.

Why go? Inside the permanent “Nuestras Historias” exhibition, you’ll see work from famous artists like José de Páez and Miguel Cabrera as well modern pieces by Chicago-based talent such as muralist Hector Duarte and imagist Errol Ortiz.

16. 360 CHICAGO

Things to do Streeterville

What is it? Sitting atop one of the tallest buildings on Michigan Avenue, this observatory places you 1,000 feet in the air, allowing visitors to see four different states on a clear day.

Why go? Daredevils will want to test their mettle on 360 CHICAGO’s TILT attraction, which dares guests to lean over the side of the building and look down at the busy streets below. If you’ve got a fear of heights, you might want to rethink your trip.


17. Adler Planetarium

Museums Science and technology Museum Campus

What is it? Visitors can explore astronomy and astrophysics at the Adler Planetarium, which sits at the outermost tip of Museum Campus (and offers some amazing views of the Chicago skyline).

Why go? Learn about the history of U.S. space exploration and take peek inside the tiny Gemini 12 capsule (which took two astronauts to space and back) in the “Mission Moon” exhibition. Then head over to the museum’s Grainger Sky Theater, which uses multiple projectors to screen immersive films on a 70-foot-diameter dome.

18. Goose Island Fulton Street Brewery

Bars Breweries United Center

What is it? One of Chicago's oldest craft breweries produces beloved beers at this facility, which also contains a barrel aging warehouse and a sleek taproom where visitors can grab a drink.

Why go? Show up Wednesday through Sunday to take a tour of Goose Island's brewery, where you'll learn about how beer is developed, produced and bottled (or canned). After the tour, ask a bartender in the taproom if there's any Bourbon County Brand Stout available for tasting.


19. Willis Tower Skydeck

Things to do Loop

What is it? You can’t get much higher in Chicago than the Willis Tower’s Skydeck, which is located on the building’s 103rd floor—1,353 feet above the city.

Why go? You’re essentially obligated to snap a selfie in the Skydeck’s Ledge—a glass box that hangs over the side of the building, giving you some breathtaking views of the urban expanse surrounding you (and beneath you). Bella vista.

Photograph: Martha Williams

20. Chicago Cultural Center

Museums Art and design Loop

What is it? Cultural events and the arts are the focus of this public building, which also happens to contain the world’s largest stained glass Tiffany dome.

Why go? There’s always something happening in the Chicago Cultural Center, including free concerts in the Preston Bradley Hall and art exhibitions on the third floor. Best of all, you’ll never have to pay admission.

Photograph: Max Herman

21. Music Box Theatre

Movie theaters Independent Wrigleyville

What is it? This beloved two-screen Lakeview movie house doesn’t usually show the latest blockbusters, but it does screen a curated selection of films in a vintage theater with clouds projected on its ceiling.

Why go? Fans of arthouse, limited-release and 70mm films will love the Music Box’s lineup of screenings and midnight movies. Before (or after) the show, check out the adjacent lounge, where you can order a beer and munch on popcorn topped with real butter.

navy pier fountain
Photograph: Jordan Avery

22. Navy Pier

Things to do Literary events Streeterville

What is it? Tourists flock to this stretch of attractions, which juts out into the waters of Lake Michigan. Navy Pier is home to a 200-foot Ferris wheel, the city’s only real IMAX screen, Chicago Children's Museum, Chicago Shakespeare Theater and plentiful dining options.

Why go? The sheer concentration of interesting things to do makes Navy Pier a great place for the whole family. See the city from a new perspective on the Ferris wheel, book a show at the Chicago Shakespeare Theater, board a boat tour or sip a drink at Offshore—the world's largest rooftop bar.

Humboldt Park
Photograph: Jaclyn Rivas

23. Humboldt Park

Things to do Humboldt Park

What is it? Filled with lagoons, pedestrian paths, wide-open fields and a boathouse, Humboldt Park is one of the biggest stretches of green space on Chicago’s West Side.

Why go? Set in a predominantly Puerto Rican neighborhood, this park comes alive in the summer. You’ll find vendors selling mofongo (fried plantains are stuffed with meat), dogs running through the fields and people dining at the boathouse’s restaurant.

Chicago History Museum
Photograph: Joseph Aaron Campbell

24. Chicago History Museum

Museums History Lincoln Park

What is it: Not so long ago this vibrant museum was the stodgy ol' Chicago Historical Society, which let you cull through thousands of archived photographs and curio. That library still exists, but joining it are several permanent and temporary exhibits, the largest of which is "Chicago: Crossroads of America," a treasure trove of historical objects, including a chunk of the original Fort Dearborn.

Why go: Calling all history buffs...if you want an in-depth look at the places and people that make Chicago what it is today, it's worth a visit.

GYG Chicago TTD


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