Chicago River
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The 32 best Chicago attractions

The best Chicago attractions include museums, vast city parks, jazz clubs and theaters

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Chicago might be the Second City, but our attractions are first class. Need proof? Just take a look at the many Chicago museums, where you'll find everything from the best-preserved T.Rex skeleton ever discovered, to paintings from Van Gogh and Picasso. Or if nature's more your thing, take a walk through the mesmerizing parks and gardens, home to some of the best public art in Chicago (hello, The Bean).

You can also spend a day swimming in Lake Michigan's surprisingly huge freshwater waves at one of the many Chicago beaches, see a jazz show at a bar once frequented by Al Capone, or have a Michelin-starred meal at one of the best Chicago restaurants... the list goes on. Whether it's your first time on Chicago or you want to see more of the city you live in, check out our curated list of the best attractions in Chicago.

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This guide was written by Zach Long, an editor based in Chicago. At Time Out, all of our travel guides are written by local writers who know their cities inside out. For more about how we curate, see our editorial guidelines.

Best Chicago attractions

  • Museums
  • Art and design
  • Grant Park
  • price 2 of 4

What is it? Located in downtown Chicago, the Art Institute is a great art museum that is home to more than 300,000 artworks that span centuries.

Why go? Here, you can find some of the world’s most iconic paintings like Georges Seurat’s A Sunday on La Grande Jatte (which you may have seen in the cinematic classic Ferris Bueller’s Day Off), Edward Hopper's Nighthawks and Grant Wood's American Gothic. Afterwards, explore the stunning Modern Wing, itself a work of art by architect Renzo Piano, or special exhibitions like Life and Afterlife in Ancient Egypt, featuring artworks and artifacts spanning 3,000 years.

  • Things to do
  • Streeterville
  • price 2 of 4

What is it? Sitting right at the top of the towering 875 N Michigan Avenue building (formerly the John Hancock building), this observation deck places you 1,030 feet in the air. On a clear day, visitors can see four different states (Illinois, Indiana, Wisconsin and Michigan).

Why go? If you want to do more than just take a really good look at the view then you should probably test your mettle on 360 Chicago’s TILT attraction, which dares guests to not freak out as the observation deck is tilted (duh) out over the busy streets below. If you’ve got a fear of heights, this may not be for you.

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  • Museums
  • Science and technology
  • Museum Campus
  • price 2 of 4

What is it? In 1893, this huge natural history museum was created to become the home to biological and anthropological collections. And, fun fact: It has more dinosaur bones and ancient artifacts than any other institution in Chicago.

Why go? Take a trip here and be transported back in time. Here, you'll find a recreation of an ancient Egyptian tomb, stand beneath a towering skeleton of Máximo the titanosaur, or encounter Chicago's most famous prehistoric resident, SUE the T. Rex, the largest and most complete T. Rex fossil skeleton ever found. Fuel your passion for discovery with dinosaurs, ancient artifacts, cultural insights and groundbreaking science.

  • Attractions
  • Parks and gardens
  • Millennium Park

What is it? One of the most popular places to spend time outdoors in the city, Millennium Park really is vast, covering a massive 24.5 acres. It hosts well-known pieces of public art and a long list of special events, including free concerts and movie screenings in the summer—plus it’s also very good for a nice sit-down.

Why go? Snap a requisite selfie in front of the hulking Cloud Gate (a.k.a. the Bean), take a walk to the Boeing Galleries, go for a stroll through the serene Lurie Gardens or relax on the lawn in front of the Frank Gehry-designed Jay Pritzker Pavilion.

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  • Museums
  • Science and technology
  • Hyde Park
  • price 2 of 4

What is it? Interactivity is the name of the game at the Museum of Science and Industry, a long-running Hyde Park institution and the largest science center in the Western Hemisphere. It boasts such attractions as a mirror maze, a simulated tornado and an entire WWII-era U-505 submarine.

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. Right now MSI is hosting Pompeii: The Exhibition, dedicated to the ancient Roman city that was destroyed by a volcanic eruption 1,900 years ago.

  • Sports and fitness
  • Baseball & softball
  • Wrigleyville
  • price 1 of 4

What is it? Built in 1914, this timeless institution is home to the city’s North Side baseball team, the Chicago Cubs.

Why go? Whether it’s a weekday afternoon or a Saturday night game, expect a sold-out crowd of faithful fans as well as out-of-towners who have made the pilgrimage just to visit the venerable stadium. Even if you have no interest in baseball, you can grab a Chicago-style hot dog and soak in the electric atmosphere. And when the last out has been recorded, head over to the myriad of neighborinig bars and restaurants to keep the good times going.

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  • Attractions
  • Parks and gardens
  • Humboldt Park

What is it? This is Chicago’s version of NYC's High Line,  a 2.7-mile stretch of an abandoned elevated rail line. It has now been revamped into a pedestrian path that connects Logan Square, Humboldt Park, Bucktown and Wicker Park.

Why go? Try coming here for a run, or even take a bike along and quickly get around to many different neighborhoods, with more than a dozen entrance and exit points along the route. You'll see some great art on your journey.

  • Attractions
  • Zoo and aquariums
  • Museum Campus
  • price 3 of 4

What is it? This Museum Campus staple is the home to thousands of aquatic creatures from all around the world, including adorable rockhopper penguins, a truly impressive selection of sharks 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 penguin, otter or an adorable beluga whale.

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  • Things to do

What is it? One of the oldest Chinese-American communities in the country.

Why go? Explore a variety of Asian businesses, learn about Chinese culture by checking out a museum or have a picnic in a beautiful park when you visit Chinatown. There’s no shortage of things to do and you can easily spend an entire day wandering the South Side neighborhood. Best of all, a seemingly endless wealth of restaurants are at the ready to help you refuel once you’re worked up an appetite, so prepare to feast on dumplings, noodles, barbecued meats and much more. 

  • Cocktail bars
  • Uptown
  • price 2 of 4

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—his associate ‘Machine Gun’ Jack McGurn was even a part-owner).

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—weekdays it shuts at a whimsical 1:11am—but you’ll usually need to show up early if you want to score a good seat.

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  • Things to do
  • South Shore

What is it? This epic 18-mile trail stretches all the way from Hollywood Avenue to 71st Street. On it you'll find walkers, runners and cyclists, getting their daily exercise and soaking in the glorious lakeside views.

Why go? Unsurprisingly the trail is hugely popular—prepare to fend off crowds in summer, though it's worthwhile to make a trip for the view and easy access to the lake for a dip. 

  • Dive bars
  • River West/West Town
  • price 1 of 4

What is it? Situated in a tiny house on a nondescript industrial corridor is one of Chicago's smallest and most hallowed independent music venues.

Why go? It can be difficult to reach this tucked-away spot via public transportation, but it is worth it for the cheap beer, fresh sounds and DJs dropping nostalgia, from Prince to Devo.

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13. Chicago Architecture Center River Cruise

What is it? A 90-minute boat tour on the Chicago River.

Why go? You may be familiar with the city’s gorgeous skyline, but do you know the deep history behind it? The Chicago Architecture Center's renowned boat cruise will take you down the Chicago River and give you the fascinating scoop on more than 50 buildings along the way. It’s the perfect way to see the city from new angles and learn something in the process.

  • 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. Want to snag a souvenir? Stop by Buddy, a shop showcasing local artists.

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  • Things to do
  • Loop

What is it? The Riverwalk provides a pedestrian path along the city’s most popular waterway as it hugs the banks of the main branch of the Chicago River. It’s 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. Plus, it's the best spot to take in the late night Art on theMart, which projects images on the side of Merchandise Mart in the evenings.

  • Music
  • Music venues
  • Loop
  • price 3 of 4

What is it? A hundred-year-old theater in the heart of downtown.

Why go? From Aretha Franklin to Frank Sinatra, some of the biggest names in the world have performed at this legendary, 3,600-seat theater. You can catch all types of concerts and stand-up sets here every week. If you’re more interested in the history side of things, book a tour that lets you explore the venue and even stand on the historic stage!

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  • Things to do
  • Literary events
  • Pullman
  • price 1 of 4

What is it? This destination houses exhibits about the growth and preservation of this historic South Side neighborhood, site of the 1894 Pullman Strike and other important moments in U.S. labor history.

Why go? Back in the 1880s, businessman George Pullman built a company town to house employees for his eponymous railroad sleeper car company. The town was annexed into Chicago at the turn of the 20th century, and the industrial complex has since been designated a National Monument. Swing by the Visitors Center on the first Sunday of every month for a guided tour.

  • Museums
  • History
  • Lincoln Park

What is it: Once upon a time this museum was just the stodgy old Chicago Historical Society, which let you sift 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 fascinating historical objects, including a chunk of the original Fort Dearborn.

Why go: If you want an in-depth look at the people, places and things that make Chicago what it is today, the History Museum is well worth a visit.

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  • Comedy
  • Comedy clubs
  • Lincoln Park
  • price 2 of 4

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.

  • Things to do
  • Literary events
  • Streeterville

What is it? Navy Pier is a popular spot for tourists to flock to, and it stretches out into the waters of Lake Michigan. It's also home to a 200-foot Ferris wheel, Chicago Children's Museum, Chicago Shakespeare Theater and plentiful dining options.

Why go? This is a great place to bring the whole family along to, as there's something to do for everyone. You can take a ride on the Ferris wheel, take a boat tour or even visit the world's largest rooftop bar, Offshore.

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  • Museums
  • Art and design
  • Streeterville
  • price 1 of 4

What is it? This iconic Chicago museum mainstay is a destination for cutting edge exhibitions and programming. It hosts one of the largest collections of contemporary art in the United States.

Why go? Take in a constantly shifting lineup of exhibitions, including touring shows from the likes of Takashi Murakami and Kerry James Marshall, or stop by the MCA Store, where you'll find everything from ceramics made by local artists to apparel from internationally-renowned designers.

What is it? Founded in 1961 by educator and artist Margaret Taylor Burroughs, the DuSable Museum is the country's oldest independent African American museum. The museum is named for Jean Baptiste Point DuSable, a Haitian trader who is considered the first permanent resident of Chicago, and holds more than 15,000 pieces. Pay a visit to see paintings, sculptures, print works and historical memorabilia relating to the history, contributions and experiences of African and African American people.

Why go? The DuSable Museum hosts a variety of exhibitions focusing on national, local and global Black history and culture, as well as timely programming—current highlights include "Fighting Racism in the Trenches," which chronicles the story of World War I veteran Kathryn Magnolia Johnson.

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  • Attractions
  • Historic buildings and sites
  • Hyde Park
  • price 1 of 4

What is it? This house is widely considered to be the greatest example of architect Frank Lloyd Wright's signature Prairie-style architecture. It was inspired by the flat Midwestern plains when it was constructed in 1910.

Why go? It's free to admire the building from outside. But if you want to get the full experience, snag a ticket for a tour offered by the Frank Lloyd Wright Trust, you can go inside and see the original art glass accents, restored furniture and a fireplace that divides the home's living and dining areas.

  • Art
  • Installation

What is it? An interactive experience based around art and technology that encourages guests to reconsider the world around them.

Why go? The WNDR Museum is the home of Chicago's largest infinity mirror room, LOVE IS CALLING, created by Japanese artist Yayoi Kusama. After you snap a selfie inside of it, check out more one-of-a-kind art installations, including a room dedicated to the work of artist Keith Haring and a hallway that features a light-up floor.

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  • Movie theaters
  • Independent
  • Wrigleyville

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

Why go? The Music Box is one of the best spots in town to see movies that don't typically make it to the multiplex. Think arthouse releases, documentaries and foreign language films. It’s also got a comfortable lounge and garden, perfect for killing some time before or after a film. If you don't feel like leaving the house to see a flick, you can rent one through the Music Box Direct streaming platform.

  • Things to do
  • Literary events
  • Woodlawn

What is it? You might know Jackson Park best for the fact that it served as the site of the World’s Columbian Exposition of 1893. It's also a great place to visit to get lost in nature, without even having to leave the city.

Why go? Take a walk through the Garden of the Phoenix and see Yoko Ono's stunning Skylanding sculpture. Or head over to the iconic Statue of the Republic at the intersection of Hayes and Richards Drives. Or, if you’re really looking for a ramble, take a detour to the nearby Midway Plaisance Park, which leads to Washington Park.

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  • Museums
  • Art and design
  • Lower West Side

What is it? Located in the Latino neighborhood of Pilsen, this cultural institution hosts one of the country’s largest collections 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 Héctor Duarte and imagist Errol Ortiz.

  • Attractions
  • Parks and gardens
  • East Garfield Park

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

Why go? Make sure to secure a (free!) reservation online and then stop by to admire the gigantic trees that fill the Palm House, or the Jurassic Park-evoking Fern Room, designed to show you what Illinois may have looked like millions of years in the past. In the warmer months, be sure to make time to explore the sprawling outdoor gardens too. 

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  • Things to do
  • Lincoln Park

What is it? It's located smack dab in the middle of Lincoln Park, and is home to more than 1,000 animals, including lions, bears, apes and red pandas! 

Why go? You don't even need to open your purse to come here, as it's the only remaining free zoo in Chicago, so just walk right in! It's a great place to take the kids to and requires very little planning. They even offer parties for adults at night, if that's your bag. 

  • Things to do
  • Humboldt Park

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

Why go? Humboldt Park is especially great in the warmer months, when it becomes something of a community hub, attracting crowds who come to enjoy the views of the lagoons from the boathouse, eat Puerto Rican food sold by vendors throughout the park and ramble along the winding paths.

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  • Breweries
  • United Center

What is it? Goose Island, one of Chicago's oldest craft breweries, produces many of its beloved beers at this facility. It also contains a barrel aging warehouse and a sleek taproom where visitors can pop in for a drink.

Why go? Whether you’re after a fresh-poured Goose Island beer or you’re on the lookout for a rarity (including the sought-after Bourbon County Stout and its many variants), you can grab a seat in the Fulton Street brewery's taproom or patio. 

32. The B_Line (Hubbard Street Murals)

What is it? Back in 1971, artist Ricardo Alonzo and local volunteers from the West Town Community Art Center filled a stretch of Hubbard Street in the West Loop with vivid murals on environmental themes as a street art project. Now, with curator and managing director Levar Hoard at the helm, local artists have been working to restore and reimagine this open-air street art gallery since 2019.

Why go? There are many incredible places to view street art in Chicago, but The B_Line, which runs along West Hubbard Street roughly between Racine and Halsted, is diverse, vivid and a clash of past and present—you'll see some of the original works alongside newer landmarks, including a powerful tribute to late Chicago rapper Juice WRLD.

GYG Chicago TTD

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