23 Best Things to Do in Chicago
Home to 77 neighborhoods, a robust lineup of festivals, a sprawling waterfront, and charming parks and walkways throughout, Chicago packs in something for every one of its locals. Add to that list award-winning theaters, iconic architecture, and a dynamic dining scene, and you’re looking at a world-class destination, too—smack dab in America’s heartland. The city’s draws only continue to grow, thanks to arrivals in everything from music venues to Michelin-starred restaurants—and the town’s hospitality remains strong, invested in helping others to enjoy those experiences across the board. From an education in the arts to an entirely outdoors itinerary (and plenty of easy-to-elegant noshes along the way), here are some of the best things to do in Chicago now.
Read our complete Chicago travel guide here.
This gallery has been updated with new information since its original publish date.
Brian kinyonactivityGarfield Park Conservatory
Step into the humid, glass-enclosed domes of Garfield Park where the air is clean thanks to thousands of jewel-toned plant specimens filtering toxins throughout. The space is fashionably untamed across its verdant showcase of flora from wet and dry environments, and those between. Spread across twelve acres, there's abundance year-round, from the colorful spring flower show to permanent indoor exhibits and holiday displays. Plant and garden enthusiasts should make the conservatory—easily accessed by Green Line—one of their stops.
Huge Galdones/Pizza City USAactivityPizza City USA
In writing his book Pizza City USA, James Beard Award-winning food reporter Steve Dolinsky had organized the city into 10 different styles of pizza, quickly understanding Chicago’s wide array of pie styles. That research led him to start a tour showcasing that range, offering him and a team of “doughcents” a chance to tout Chicago’s diverse pizza scene to visitors and locals alike. There are four different kinds of tours, each exploring 3-4 styles of pizza. A walking tour Friday nights (downtown), a bus tour (various neighborhoods), and a walking tour (West Loop) on Saturdays, and a walking tour on Sundays (Bucktown/Wicker Park). Though the venues vary by tour, you can expect stops at favorites like Labriola (deep pan), My Pi (deep-dish), Robert’s (artisan), Paulie Gee’s Logan Square (Detroit-style), Eataly, and Bar Cargo (Roman). Get ready to grow your pizza IQ—in addition to discussing the range of pie styles, the team shares plenty of ‘za terminology and local history.
GettyactivityUrban Kayaks
Kayaking on the Chicago River or lake front is one way to shake up your perspective while visiting. Urban Kayaks offers tours along either. Move through the pulsing heart of the city on the river or travel Lake Michigan and circle Museum Campus (featuring the Field Museum, Adler Planetarium, Shedd Aquarium and Soldier Field). A night tour on the river boasts views of the glowing Merchandise Mart, which is showered in rotating, digital art displays projected onto the building. A one and a half hour skyline paddle in Lake Michigan gives you all the tourist sites without the foot traffic and crowds, showing you Grant Park and Navy Pier on a route few tourists trek.
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Catalina Florea/The Salt ShedactivityThe Salt Shed
The team responsible for some of Chicago’s best restaurants and concert halls is behind this hugely popular newcomer, housed within the iconic Morton Salt building on the North Branch of the Chicago River. The indoor-outdoor space made a soft debut last summer and continues those rollouts this year, with indoor shows this past winter and a full lineup this summer (including acts like First Aid Kit, Pretty Lights, Caamp, and Tash Sultana). Multi-level ticketing tiers help guests in selecting their vantage point for shows. Even if you don’t have prime sightlines every time (now considered the largest independent concert venue in Chicago, the space has a capacity of 5,000 for outdoor shows and 3,500 for indoors), you’re still in luck: They feature a state-of-the-art sound system by L-Acoustics. The venue also features a solid lineup of local food options, including Pizza Friendly Pizza and Café Tola. Find them in the outdoor Fairgrounds space (perfect for grabbing a bite pre-show).
©2022 The Morton ArboretumactivityThe Morton Arboretum
Located about 30 minutes west of downtown Chicago, the Morton Arboretum feels like a world away. It's a pastoral escape that feeds the mind and heart. Art installations on site are rotated seasonally, several of them are dedicated to the natural sciences, such as the living exhibit dedicated to tree growth. 'Human+Nature' is the current installation here, showcasing the work of acclaimed sculptor Daniel Popper. Five pieces are currently on display in various locations across the arboretum's 1,700 acres, making this Popper's largest exhibition to date anywhere in the world. Open from 7:00 a.m. to sunset, daily—it's a relative bargain at $16 a ticket. With a maze garden and over 16 miles of hiking trail, this is the ideal urban getaway for outdoorsy sorts looking to decompress.
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Stephen GreenactivityWrigley Field
Iconic Wrigley Field is arguably one of Chicago's most storied landmarks, with millions of baseball fans flocking to the stadium just to get a photo in front of the iconic Wrigley Field Marquee (whether they’re rooting for the Cubs or not). The stadium anchors the Wrigleyville neighborhood, which has experienced a boon in development. A new outdoor plaza, luxury hotels, and an influx of restaurants/bars have boosted the area's cultural cachet, so it's worth hanging around before or after your stop at the stadium.
Peter McCulloughactivityMuseum of Contemporary Art, Chicago
$The MCA is one of the city’s museums that’s in a near constant state of transition. With its relatively small permanent collection, it relies on special shows—from large scale installations to video, fashion, music, photography, and more—that showcase just as many rising local talents and underground, avant-garde renegades as recognizable names. Past exhibits include David Bowie Is, Takashi Murakami: The Octopus Eats Its Own Leg, and Virgil Abloh: Figures of Speech. It also has one of the best gift shops (ever) and is home to Marisol, where chef Jason Hammel puts forth thoughtful, seasonal cuisine. Come summer, visit for their “Tuesday on the Terrace” music series, along with 21 Minus, an annual festival celebrating the next generation of artists.
GettyactivityMidway Plaisance
Known simply as the Midway, this mile-long natural stretch on the South Side connects the east end's Washington Park to Jackson Park on the west. Once the site of amusements during the 1893 Columbian World's Exposition (AKA World's Fair), the Midway is flanked by Hyde Park's noted gothic architecture, particularly the University of Chicago campus, and tree-lined boulevards, as well as outfitted with an ice skating rink and other facilities to keep folks visiting year-round.
Todd RosenbergactivityLincoln Park Zoo
Located in the heart of Chicago's Lincoln Park, this zoo offers free, family-friendly entertainment year-round including the festive Zoolights around the holidays (reservations are required for all visits though). The sprawling grounds are seamlessly woven into the park’s landscape, balancing open, natural spaces and numerous animal exhibits. If you skip the pricey concessions (but maybe spring for a paddle boat ride), Lincoln Park Zoo is a great option to keep all ages occupied while staying on a budget. Visit the animals, take a spin on the AT&T Endangered Species Carousel or the Lionel Train Adventure, and enjoy family-friendly dining options, such as Bird’s Eye Bar & Grill or the Patio at Café Brauer.
Courtesy Art Institute of ChicagoactivityArt Institute of Chicago
$If you're coming to Chicago for culture, you're hitting the Art Institute first. It is the city's grandest museum, a Beaux Arts gem flanked by two bronze lions that are as much a symbol of the city as the Willis Tower and it has as fine an impressionist collection as you'll find anywhere. While you're there, plan to take a stroll through Millennium Park next door.
Adam AlexanderactivityBloomingdale Trail (The 606)
Chicago's answer to New York's High Line, the Bloomingdale Trail—a.k.a. The 606—is a nearly three-mile, elevated greenway running west and east on the city’s North Side. Unlike its NYC counterpart, the trails are wide enough to accommodate active patrons running, walking and cycling without running off more casual strollers, the formerly abandoned rail line is also lined with public art installations and gardens. During fairer weather, the trail also hosts various free events for families with young children.
Restoration Hardware/3 Arts Club Caferestaurant3 Arts Club Cafe
$$$Today there are more than 15 RH restaurants across the nation, but Chicago’s 3 Arts Club Café, which opened in 2015, was the first. Guests will discover it within Restoration Hardware’s 70,000-square-foot design gallery, which formerly functioned as the Three Arts Club, a residence built in 1914 for young women studying music, drama and the visual arts. Today, that space has been royally reimagined in the hands of RH, turning the six-story building into a lavishly outfitted labyrinth featuring its myriad décor whimsies (from the brand’s Design Atelier line to its children’s collections). Come here with friends or a special plus one, and arrive early—you'll want to factor in time for grabbing a coupe and perusing the historic property as you await your table.
GettyactivityHumboldt Park
One of Chicago's prettiest parks, this nearly 200-acre green space is located within the larger neighborhood of Humboldt Park (both are named for German naturalist Alexander von Humboldt). It's home to several statues—including one of its namesake, and two bison that were placed there during the 1893 World's Fair—as well as the National Museum of Puerto Rican Arts & Culture, located in the park's former stables. It's easy to drop in if you're headed down the 606 trail, but the park is big enough that it could take more than half a day to do all of it, so it's best if you're not in a rush.
Kirsten MiccoliactivityThe Second City
$$Tina Fey, Bill Murray, and Chris Farley all grew out of the scene at Second City and it continues to nurture some of the country's best comedy talent. Over three stages and four intimate studio theaters, there's plenty to see. The Mainstage show, featuring that season's top billed act, features long-form improv sketch, and is often packed on marquee nights. The same can be said for the e.t.c. Theater, which showcases up-and-comers, and the Up Comedy Club, for stand-up comic acts. The shows tend to be full, and ticketed for general admission, so come early to snag a prime seat. (Pro-tip: Avoid front row if you don't want to crane your neck all night.)
Courtesy Lakeshore TrailactivityChicago Lakefront Trail
The 18-mile long trail hugs the coast of Lake Michigan, offering almost all manner of activity along the shore. From sandy beaches and sprawling parks, to some of the best views of the Chicago skyline, the Lakefront Path is one of the city's great public treasures, enjoyed by visitors and locals alike. Runners and cyclists love the width and ease of use of the trail, while intramural type teams make use of the many open spaces found up and down the path. If you don't want to run around, there’s plenty of room to just sit and people watch, as well as check out a number of art installations that pop up throughout the year.
Todd Rosenberg/Auditorium TheatreactivityAuditorium Theatre
Inspired to build a theater that would benefit the city and serve as the world’s largest and most ornate building, Chicago businessman Ferdinand Wythe Peck began plans for the Auditorium Theatre and debuted the venue in 1889. Since then, the theater has been the site of major historical events and performances and earned impressive titles along the way (including a National Historic Landmark designation). Keep an eye on this season's calendar for events with Tom Hanks, The National, and Loreena McKennitt, among others. Anyone seeking a dose of the arts in elevated, historic environs will do well by a visit here. Gather friends for a speaker event or concert, or make it a date night.
GettybarGreen Mill
$Do not come here expecting fancy drinks—or anything fancy, really. This is living, breathing history. And it's a rocking good time. The Green Mill is a warm and inviting throwback to a bygone era. There’s live jazz, cheap drinks, and loads of local history (Al Capone used to have a booth reserved here during Prohibition); what's not to love? Bar eats are not on the menu here. Bring your own potato chips if you think you'll need a snack (no one will judge you). The craft beer list has expanded commendably over the past few years. So grab yourself a cold one or a whiskey soda and see where the night takes you.
Courtesy Chicago Architecture Foundation RiveractivityChicago Architecture Foundation River Cruise
Run by the Chicago Architecture Center, the Architecture River Tour is one of the most polished operations in town (and a wonderful alternative to some of the cheesier tours). Taking place on a barge in spring, summer, and fairer fall weather, the cruise explores Chicago's beginnings from various branches of the Chicago River—offering both day and evening tours. While groups are typically large, the Architecture Center-trained docent speaks via loudspeaker, audible from throughout the boat. (Pro-tip: Head straight upstairs when you board and snag a seat in the rear for optimal views.) In 90 minutes, you'll get to know 50 buildings along the Chicago River, hear secrets about a map of the river's topography hidden in plain sight, and learn about the only skyscraper in the skyline designed by an award-winning female architect.
AlamyactivityPromontory Point
This man-made peninsula in Burnham Park has become a favorite gathering and photo shoot spot for locals due to its manicured landscape and rock formations along the lakefront. Our plan of attack here is to have a picnic at the point, then walk among a number of public art works edging the surrounding park. Some of the most interesting public art installations and gathering spaces, such as Sounding Bronzeville and La Ronda Parakata, are actually within the Burnham Wildlife Corridor, which is composed of the Burnham Centennial Prairie, Burnham Nature Sanctuary, and McCormick Bird Sanctuary.
Courtesy Intuit: The Center for Intuitive and Outsider ArtactivityIntuit: The Center for Intuitive and Outsider Art
Among the only museums in the world dedicated wholly to outsider art, Intuit is an impressive shrine to self-taught creators across all forms of media. Beyond an unassuming, brick facade, you’ll brush up against a concise-yet-vibrant collection of paintings, sculptures and assorted ephemera. The collected work draws you in with an air of unconventional audacity. This is a whimsical environment with an industrial edge. Exhibits are spread out with ample room for wandering and gazing at your leisure. The museum is curated by passionate docents who are committed to the cause of promoting the artistic output of marginalized creatives.
Courtesy Chicago Botanic GardenactivityChicago Botanic Garden
The Chicago Botanic Garden, a 385-acre living plant museum, features 28 distinct gardens and four natural areas. Those figures are impressive enough to draw more than one million visitors annually, making it one of the most frequented botanical gardens in the United States. Inside the gates, the Garden’s living collections feature more than 2.8 million plants from around the world that grow well in the Chicago area and are adapted to Midwest climate and soils. Expect to see a lush array of trees, shrubs, vines, and tropical plants, among other varieties.
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