22 best things to do in Chicago

Address: Goodman Theatre, 170 N Dearborn Street, Chicago, IL 60601
Website: goodmantheatre.org

Pizza City USA

In writing his book Pizza City USA, James Beard Award-winning food reporter Steve Dolinsky organised 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 three to four styles of pizza. A walking tour on Friday nights (downtown), a bus tour (various neighbourhoods), a walking tour on Saturdays (West Loop), and a walking tour on Sundays (Bucktown/Wicker Park). Though the venues vary by tour, you can expect stops at favourites 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.

Address: Pizza City USA, 1156 W Ohio St #1W, Chicago, IL 60647
Website: pizzacityusa.com

Green City Market

Today, the organisation’s mission remains steadfast: to champion sustainable farmers, educate the community, and expand access to locally grown food. Visitors can support the cause by attending the weekly markets or by purchasing tickets to their annual fundraiser, Chef BBQ. Held in early September at the Lincoln Park location, the event gathers the city’s best chefs, brewers, and distillers for an evening of bites and sips incorporating favourite market finds. The team works with 67 Midwest vendors across their locations, those who specialise in everything from jams and artisan breads to hyper-fresh produce and pastries. Whichever of the three markets you choose to visit, be sure to arrive early for the best picks of them all. Those looking to learn more about the Midwest's food system and enjoy some delicious tastes along the way will do well by a morning stroll or lunch outing here. And with ample local treasures like honey, hot sauce, and tea, consider your souvenir shopping complete.

Address: Green City Market, 1817 N Clark St., Chicago, Illinois 60614
Website: greencitymarket.org

Urban Kayaks

Kayaking on the Chicago River or the lakefront is one way to shake up your perspective while visiting. Urban Kayaks offers tours along either, including historic tours, and has options for sunset and nighttime trips. 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) for beautiful views before returning to the harbour. Not sure of your skill level? There are classes and excursions for all experience and fitness levels. A night tour on the river offers views of the glowing Merchandise Mart, which is illuminated by rotating digital art displays projected onto the building. A one-and-a-half-hour skyline paddle in Lake Michigan offers a unique perspective on the tourist sites, without the foot traffic and crowds, showcasing Grant Park and Navy Pier on a route few tourists venture.

Address: Urban Kayaks on the Chicago River, 435 E, Chicago Riverwalk, Chicago, IL 60601
Website: urbankayaks.com

The Salt Shed

The team responsible for some of Chicago’s best restaurants and concert halls (Empty Bottle, Thalia Hall, SPACE, The Promontory) is behind this hugely popular music venue, housed within the iconic Morton Salt building on the North Branch of the Chicago River. The indoor-outdoor space continues to welcome beloved acts like Jack White, PJ Harvey, Stephen Sanchez, Sharon Van Etten, Mt. Joy, and Gary Clark Jr. Expect a robust lineup of musical talent across several genres (namely rock, pop, and hip-hop). Beyond its concerts, the venue hosts year-round programming, including the SummerSalt Vintage Market and "Crying at the Shed,” a Valentine’s Day film festival featuring tearjerkers and musical performances. Gather a group of friends for a great night of music under the stars, or plan a date night to catch your favourite act.

Address: The Salt Shed, 1357 N Elston Ave, Chicago, IL 60642
Website: saltshedchicago.com

The 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 biannually and are inspired by the natural sciences and our relationships with the natural world. The new Vivid Creatures exhibition features five colourful, larger-than-life sculptures of animals native to northern Illinois, ranging in height from eight feet to 23 feet. Created by Portland, Oregon-based artists Heather BeGaetz and Fez BeGaetz, the sculptures range from a brittle button snail to a sandhill crane, fox squirrel, and white-tailed deer. They are on display in various locations across the arboretum's 1,700 acres, with four of the five sculptures accessible along paved, ADA-compliant paths. Open from 7am to sunset, daily – it's a relative bargain starting at around £13 a ticket for adults. With a maze garden and over 16 miles of hiking trails, this is the ideal urban getaway for outdoorsy sorts looking to decompress.

Address: The Morton Arboretum, 4100 IL-53, Lisle, IL 60532
Website: mortonarb.org

Wrigley Field

Iconic Wrigley Field is arguably one of Chicago's most storied landmarks, with millions of baseball fans flocking to the ballpark just to get a photo in front of the iconic Wrigley Field Marquee (whether they’re rooting for the Cubs or not). There's not a bad seat in the house, whether you're among the 40,000 within the ballpark or the lucky residents on a surrounding "Wrigley rooftop." And that's really saying something for a professional sports stadium in the United States. The ballpark anchors the Wrigleyville neighbourhood, which now comprises the adjacent outdoor plaza Gallagher Way, Hotel Zachary, and several surrounding bars and restaurants. Special programming at Gallagher Way – such as movie nights, fitness classes, kid-friendly events, and various markets on the outdoor plaza – makes the ballpark a draw for both baseball fans and non-sports enthusiasts. It all contributes to the game day experience, so consider making a day of it here.

Address: Wrigley Field, 1060 W Addison Street, Chicago, IL 60613
Website: mlb.com

Museum of Contemporary Art, Chicago

The MCA is one of the city’s museums that is 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 recognisable names. Past exhibits include “Nick Cave: Forothermore,” “Faith Ringgold: American People,” and “Forecast Form: Art in the Caribbean Diaspora, 1990s-Today.” 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. In 2025, the MCA hosts Paul Pfeiffer: Prologue to the Story of the Birth of Freedom, and Yoko Ono’s retrospective, Music of the Mind. The MCA is currently the only US venue for her exhibition.

Address: Museum of Contemporary Art, 220 E Chicago Ave, Chicago, IL 60611
Website: mcachicago.org

Lincoln Park Zoo

Located in the heart of Chicago's Lincoln Park, this zoo offers free, family-friendly entertainment year-round (with reservations required). The sprawling grounds are seamlessly incorporated within the park, and there's a nice balance of open, natural spaces and animal exhibits so kids can check out their favourite creatures. Don't miss the recently renovated Pepper Family Wildlife Center (home to two lion prides), Regenstein Center for African Apes (an indoor-outdoor space for endangered chimpanzees and western lowland gorillas), and the Houston Family Play Treehouse, a new, accessible play space in Pritzker Family Children’s Zoo. The zoo was recently recognised as an accredited botanical garden and arboretum, so be sure to take in sights of the thousands of different plants and flowers here, too.

Address: Lincoln Park Zoo, Chicago, IL 60614
Website: lpzoo.org

Art Institute of Chicago

The Art Institute is Chicago's grandest: a Beaux Arts gem flanked by two bronze lions that are as much a symbol of the city as the Willis Tower. The massive Renzo Piano-designed Modern Wing, opened in this century, significantly expanded its galleries and added a rooftop restaurant that feels like a find, even if it's hiding in plain sight. In short, if you're coming to Chicago for culture, you're hitting the Art Institute first. The collections at the Art Institute are numerous and diverse, ranging from the blockbuster Impressionist portfolio to the quirky Thorne Miniature Rooms, which capture global architecture from the 13th to the 20th century in dollhouse proportions. There's a Medieval armoury, modern furniture, a vast Asian collection, and photography that spans the history of the medium. It's particularly strong in mid-20th-century works, thanks to Georgia O'Keeffe's donation of the Alfred Stieglitz Collection. Comprehensive is a good word for what's within these walls.

Address: The Art Institute of Chicago, 111 S Michigan Avenue, Chicago, IL 60603
Website: artic.edu

Bloomingdale Trail (The 606)

Chicago's answer to New York's High Line, the Bloomingdale Trail (also known as the 606 trail), is just under three miles of manicured running, walking, and cycling trails. Planted with native flora and a number of art installations, the elevated park is a pedestrian-friendly, east-west thoroughfare that offers a green escape from city life, if only for a little while. Located at the southwest corner of Bloomingdale Avenue and Humboldt Boulevard, student-artists from the non-profit art educator Marwen created a mural on permanent display in the park. The students, ranging from grades six to 12, spent a week photographing the vibrant Humboldt Park neighbourhood and then assembling their work into an abstract collage. The park regularly invites artists to submit their large public works, which rotate on a temporary basis.

Address: Bloomingdale Trail (The 606), 1805 N. Ridgeway Ave., Chicago, Illinois 60647
Website: the606.org

3 Arts Club Café

Today, there are more than 20 RH restaurants across the nation, but Chicago’s 3 Arts Club Café, which opened in 2015, was the first. Guests will discover it within RH’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). Explore them all, and when hunger strikes, return to floor one – it’s here you’ll find the aforementioned restaurant, where guests settle in for brunch, lunch, or dinner in a fairytale setting, surrounded by running fountains, heritage olive trees, and opulent chandeliers.

Address: 3 Arts Club Cafe at RH Chicago, 1300 N Dearborn St, Chicago, IL 60610
Website: rh.com

The Second City

Housed in Pipers Alley Mall, this storied comedy theatre, which has launched the careers of the likes of Bill Murray, Chris Farley and Tina Fey, also houses a comedy school for budding comedians, writers, and filmmakers looking to make their mark. The improv and comedy writing programs are top-notch, funnelling their talents into a variety of comedy shows, from the mainstage sketch shows to the more intimate stand-up comedy club. The Mainstage show should be your first show here: it features the actors and players who have clawed their way to the top. The material is always changing and evolving, so don't expect the same sketch or even show twice. But if you want a glimpse at Chicago's hot comedy talent, visit the e.t.c Theater, where the shows are a touch more experimental as the players train and test material for the big stage.

Address: The Second City, 230 W North Ave, Chicago, IL 60614
Website: secondcity.com

Chicago Lakefront Trail

The 18-mile-long trail hugs the coast of Lake Michigan, offering a diverse range of experiences along the shore. From calm, sandy beaches to sprawling parkland 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 appreciate the ease of the trail, while teams utilise the numerous fields and sports complexes located along the route. The trail runs north-south, even when it cuts through downtown Streeterville, the Loop, and Grant Park. The public parkways are accessible to all, with numerous places to stop, rest, and grab a snack. There are also plenty of opportunities to catch some culture off and on the trail: There's the Theater on the Lake in Lincoln Park, and the Museum Campus to the south with the Field Museum, Adler Planetarium, and Shedd Aquarium.

Website: chicagoparkdistrict.com

Chicago Electric Boat Company

What started as a business with just two electric Duffy Boats has since grown to encompass more than 45 vessels with 10 types available, ranging to hold anywhere from four to 26 guests. Guests can set sail from five locations throughout the city. Three loop locations include Marina City, Chicago Water Plaza, and the Chicago Riverwalk. A Lakefront dock offers private and public Cycleboat cruises, and Rockwell on the River offers relaxed cruises along the river’s North Branch. To enhance the experience, bring along some sailing accompaniments, such as décor and playlists (a Bluetooth speaker is available on every vessel). All cruises are BYOB for food and drink. Consider these cruises an excellent opportunity to gather a group of friends or coworkers for a low-key evening on the water – it may just be the perfect way to escape the city while still taking it all in.

Address: Chicago Electric Boat Company, 300 North State Street, STE EE, Chicago, IL 60654
Website: chicagoboatcompany.com

The Auditorium

Inspired to build a theatre 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 and debuted the venue in 1889. Since then, it has been the site of major historical events, world-class performances, and has earned impressive titles along the way (including a National Historic Landmark designation). Credit its meticulous planning and the team behind it, who envisioned a building achieving modern architectural feats at the time, and whose design has resulted in a longstanding distinction in both acoustics and architecture. Some of the most notable artists and speakers of every generation and genre have graced this stage, including Aretha Franklin, The Doors, Ruth Bader Ginsburg, Theodore Roosevelt, Stevie Wonder, Prince, Alvin Ailey American Dance Theater, and Stephen Colbert, to name a few. Keep an eye on their calendar for events featuring musicians, orchestras, comedians, films, dance, and speakers.

Address: Auditorium Theatre, 50 East Ida B. Wells Drive, Chicago, IL 60605
Website: auditoriumtheatre.org

Chicago Architecture Foundation River Cruise

The Chicago Architecture Center (CAC) River Cruise aboard First Lady is one of the most polished and storied operations in town. Taking place on a river-ready barge in spring, summer, and nicer fall weather, the cruise explores Chicago's beginnings from along all three branches of the Chicago River. The groups are large, but 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 and about the figures behind their Art Deco, neoclassical, midcentury modern, and postmodern designs. You'll learn about a secret map of the river's topography (hidden in plain sight), the only skyscraper in the skyline designed by an award-winning female architect, and even the visual jokes designers played to leave their mark on the city.

Address: 111 E. Wacker Drive, Chicago IL 60601
Website: architecture.org

Poetry Foundation

When Harriet Monroe founded Poetry in 1912, she hoped the magazine would support the work of artists everywhere and celebrate the pursuit of poetry. Her vision has had ongoing impact – in 2003 with the arrival of Poetry Foundation, and in 2011 with the debut of the foundation’s building – Chicago’s first building dedicated to poetry, and the first permanent venue for the magazine in its 100-year history. The building encompasses 22,000 square feet (including offices), and comprises a courtyard, gallery, and library with more than 40,000 volumes of poetry for all ages. There is also the Pegasus Room, where the team hosts poetry performances and readings. The centre sees a range of visitors from near and far spending time here, whether it’s an afternoon in the library, lunch hour in the courtyard, or an evening event. They are open Wednesday through Saturday, so be sure to plan accordingly – and to keep an eye on their programming, which features engaging workshops and readings throughout the year.

Address: Poetry Foundation, 61 W Superior St, Chicago, IL 60654
Website: poetryfoundation.org

Promontory Point

Promontory Point, a man-made peninsula that juts into Lake Michigan, has become a favourite gathering and photo shoot spot for locals due to its manicured landscape and rock formations along the lakefront. Part of the larger Burnham Park, the point is just one of the attractions that renowned Chicago architect and planner Daniel H. Burnham envisioned for the South Side park. Fast-forward over 100 years, and the point and surrounding acreage are still committed to preservation. After a picnic at the point, walk among several public artworks 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 gathering spaces within the Burnham Wildlife Corridor. Comprising the Burnham Centennial Prairie, Burnham Nature Sanctuary, and McCormick Bird Sanctuary, the corridor encourages visitors to reconnect meaningfully and inspire engagement in green public spaces.

Address: Burnham Park Promontory Point, 5491 S DuSable Lake Shore Dr, Chicago, IL 60615
Website: chicagoparkdistrict.com

Chicago Symphony Orchestra at Symphony Center

Formed in 1891, this orchestra remains recognised as one of the best in the world, presenting over 150 concerts annually, spanning from Baroque to contemporary music. When you aren’t experiencing the ensemble onsite, look for them at performances around town (including several nights at Highland Park’s Ravinia Music Festival). The venue specialises in classical symphonies, collaborating with some of the globe’s most respected conductors and artists to offer regular programming. There are more than 2,500 seats across several sections, each providing its own unique vantage point (including the Gray Terrace, located behind the stage and offering up-close views of the orchestra). With the sounds of Tchaikovsky, Schumann, and the like, consider this a romantic evening for two – be it a 25th anniversary or a Tuesday night.

Address: Symphony Center, 220 S Michigan Ave, Chicago, IL 60604
Website: cso.org

Chicago Botanic Garden

The Chicago Botanic Garden, a 385-acre living museum, features 28 distinct gardens and four natural areas. It draws more than one million visitors annually, making it one of the most frequented public gardens in the United States. The Garden’s living collections feature more than 2.7 million plants from around the world that thrive in the Chicago area and are well-adapted to the Midwest climate and soils. Expect to see a lush array of trees, shrubs, vines, and tropical plants, as well as other diverse varieties. The team here makes a solid effort to accommodate everyone who visits, offering wheelchairs at the information desk, accessible parking, electric scooters, and the option to bring service animals. The Buehler Enabling Garden is particularly notable: It's a teaching garden that showcases green thumb techniques for individuals who use wheelchairs.

Address: Chicago Botanic Garden, 1000 Lake Cook Road, Glencoe, IL 60022
Website: chicagobotanic.org

This article was first published on Condé Nast Traveler.