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The 27 best Chicago attractions

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

Written by
Zach Long
Contributors
Emma Krupp
&
Rhys Thomas
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Chicago might be the Second City, but our attractions are first class. Need evidence of that fact? Look no further than the many Chicago museums, where you'll find everything from the best-preserved T.Rex skeleton ever found to paintings from Van Gogh and Picasso. Or take a stroll through our gorgeous parks and gardens, home to some of the best public art in Chicago (hello to The Bean). Or spend a day swimming in Lake Michigan's surprisingly huge freshwater waves at one of the many Chicago beaches, or 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 you’re from out of town and visiting for the first time or a lifelong Chicagoan looking to see a little more of their home city, we’ve curated a list of the very best attracts Chicago has to offer, just for you.

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Best Chicago attractions

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

What is it? There are more than 300,000 artworks housed inside the Art Institiute, one of the city’s – and, indeed, the country’s best-known cultural institutions.

Why go? You can finally come face to face with one of the world’s most iconic 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. Once you’ve done that, try exploring the expansive collection of contemporary works in the museum’s Modern Wing. Its current exhibition Fantastic Landscapes: Hokusai and Hiroshige collects fantastical landscapes by the legendary Japanese printmakers.

  • Things to do
  • Lincoln Park

What is it? Located smack bang in the middle of Lincoln Park, this 35-acre zoo houses more than 1,000 animals. Even better: it’s absolutely free, one of the last remaining great free zoos in the country.

Why go? Most of the zoo’s Covid restrictions are now gone, meaning you don’t need a reservation and the indoor exhibits are open—though mask-wearing is advised. It’s the perfect no-planning-needed day out with the kids. Or as a special treat for adults, why not book in to one of the block party-style after hours adult nights.

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  • Things to do
  • Streeterville
  • price 2 of 4

What is it? Sitting right at the top of the towering 875 N Michigan Avenue building (f.k.a. the John Hancock building), this observation deck places you 1,000 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.

  • 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 reservation online and then stop by to admire the gigantic trees that fill the Palm Room, or the Fern Room, designed to show you what Illinois may have looked like millions of years in the past.

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

What is it? This massive natural history museum was founded to house the biological and anthropological collections assembled for the World’s Columbian Exposition of 1893. It 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 skeleton of Máximo the titanosaur or stare at the myriad sparkling stones in the Grainger Hall of Gems. And don't forget to visit Sue the T. rex, the iconic lizard king who also apparently finds time to maintain a sassy Twitter account.

  • 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—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), catch free live music as part of the Millennium Park Summer Music Series, 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 a traveling exhibit devoted to Marvel superheroes—it’s very popular but you might just snag a ticket before it leaves in October

  • Attractions
  • Parks and gardens
  • Humboldt Park

What is it? Chicago’s answer to the High Line in NYC, this 2.7-mile stretch of an abandoned elevated rail line 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 traverse some of the most popular North Side neighborhoods. Plus, you’ll spot some art installations as you go.

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  • 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, 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 an adorable beluga whale.

  • 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 comfortable seeing a flick in-person, you can rent one through the Music Box Direct streaming platform.

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  • Bars
  • 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.

  • Art
  • Old Town

What is it? Animated versions of Vincent Van Gogh's iconic paintings are projected on the 35-foot walls of a space within the Germania Club Building in Old Town.

Why go? If you want to feel like you’re literally standing inside such trippily magnificent works as Starry Night and The Bedroom in Arles—which are beamed through more than 50 digital projectors —"Immersive Van Gogh" is a feast for the eyes and ears (thanks to its booming classical and electronic soundtrack). The price of admission is a bit steep, but the 35-minute show is unlike anything else on display in Chicago.

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  • Things to do
  • Literary events
  • Woodlawn

What is it? This sprawling park is perhaps best known for having served as the site of the World’s Columbian Exposition of 1893. But history aside, Jackson Park is one of our favorite spots to get lost in nature without leaving 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.

  • 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. When chilly weather sets in, the Lakefront Trail becomes markedly less crowded, while still offering the same dazzling views.

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  • Museums
  • Art and design
  • Lower West Side

What is it? Located in the traditionally Latino 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.

  • Bars
  • 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? The Hideout is open again after being closed by the pandemic, but it’s taking things cautiously: while the weather allows, shows are taking place on its outdoor patio stage (and proof of vaccination is required).

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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.

  • 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.

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  • 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 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.

  • 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 artist that opened inside the Center this year. 

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  • 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.

  • Art
  • Installation
  • West Loop

What is it? An interactive experince based around art and technology that encourages guests to reconsider the world around them. Currently, all of the installations on display are touchless.

Why go? The WNDR Musuem is the home of Chicago's only Infinity Mirror Room, 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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  • 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.

  • 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, or on your computer screen via the club's virtual shows. If you want to learn more about improv, stand-up or sketch writing, you can sign up for a class at the Training Center.

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  • Bars
  • 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 make a reservation and grab a seat on the Fulton Street Brewery's patio. 

  • 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’s inspired by the flat Midwestern plains when it was constructed in 1910.

Why go? It is of course 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.

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  • 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, 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, board a boat tour or sip a drink at Offshore—the world's largest rooftop bar.

GYG Chicago TTD

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