You may not have come to Chicago for its piles of teeth. Its living-room-sized theaters. Its late-night cafe jazz concerts. Its sculpture designed by Yoko Ono.
We certainly didn’t come for them—but we found them anyway, and now they’re some of our favorite art spots across the South Side and throughout the city of Chicago. Here are ten of the Maroon Arts staff’s favorite arts and culture spots across Chicago. From each spot, you’ll spot two more, and the journey into the heart of artness has begun.
They’re Just Making It Up As They Go Along: Chicago’s improv comedy legacy runs deep, with roots tracing back to the University of Chicago alumni who founded the influential Compass Players in 1955—a group that would evolve into the iconic Second City Theater. Although the Second City Theater may be the most famous improv venue in the country, second only to the Second City is the iO Theater. The International Olympic Theater, commonly referred to as the iO, is located in the Goose Island neighborhood on the North Side, just a five-minute walk from North/Clybourn on the Red Line. If you are looking to see improv for the first time or you’re a comedy geek, the iO’s a great place to learn about the art (and chaos) of improv without having to pay too much. The theater offers a wide array of shows, from Jane Austen–inspired sketches to Shakespearean parodies, American history reenactments to their signature long-form improvisation, where they come up with a whole play on the spot. There are shows every night from Wednesday to Sunday, and student tickets are just $10. If you catch the 8 p.m. show, you can stick around for the 10 p.m. performance for free. —Adera Craig, Senior Arts Reporter
Free, Free, Free, Free: Free books! If those two words catch your attention, check out Open Books, a nonprofit bookstore that uses its proceeds selling donated books to fund literacy programs across Chicago. Many of their titles are free, while some are sold for just a few dollars. Some of my favorite finds include a copy of Granta magazine and Michael Chabon’s Moonglow. They have two locations, one in Pilsen and one in the West Loop. —Miki Mukawa, Arts Editor
A Maroon’s Trusty Sidekick: Dora has the Map, Aladdin has the Genie, Iron Man has J.A.R.V.I.S, and the arts-inquisitive UChicago student has… the ArtsPass? Maybe it’s not the best analogy, but you get the point: ArtsPass is something you have to consult. On the ArtsPass website, you’ll find a map with an array of partner institutions around the city, many of whom offer free or heavily discounted admissions to UChicago students. It’s a great place to start if you’re looking for a one-stop shop for all things arts related in Chicago. If you attend five organizations during the year and register on Canvas, you can get free merch and treats at Café Logan! —Nolan Shaffer, Arts Editor
Flight Club: After a few weeks in Hyde Park, you’re going to want a date night away from Nella or Small Cheval. It’s a good thing that one of Chicago’s buzziest restaurants, Bronzeville Winery, is just ten blocks north of campus in the South Side’s historic Bronzeville neighborhood. Classic new age bites—blood orange brussels sprouts and sea bass with salsa verde—complement a stellar wine list that features Black-owned vineyards from across the world. A wine flight will carry you from Spain to South Africa to California. On the weekends, expect a live DJ set to fill the bright, wood-paneled dining room. Be sure to place a reservation in advance. The restaurant is an easy walk, bike, or Lyft from campus. —Noah Glasgow, Lead Arts Editor
Businéss School des Beaux Arts: The Harper Center, home to the Booth School of Business, is the last place you’d expect to find a world-famous collection of contemporary art. And yet, thanks to generous donations and the work of a five-member collections committee including the president of the Art Institute of Chicago, the school has amassed 800 pieces by nearly 200 artists, making it one of the finest collections of contemporary art in the country. It is strange and extraordinarily intimate to walk through Booth on a quiet weekend or at night and find works of art covering nearly every wall of the six-story, 415,000-square-foot building. Plus, since it’s free and on campus, the econ bros would call it low opportunity cost. And if you’re a returning student, you’ve probably walked by Giuseppe Penone’s “Ideas of Stone” between the Harper Center and the back of Ida Noyes a dozen times without realizing what it is. The tree sculpture, unique and arguably the most notable piece of public art at UChicago (perhaps vying with the concrete car), is impressive, beautiful, and haunting. —Nolan Shaffer, Arts Editor
At Wit’s Beginning: Just a short walk from the Green Line in the beautiful neighborhood of Lake View is the friendly and eclectic Theater Wit. The performing arts center, which has been a home for vibrant contemporary theatre for more than two decades, houses three intimate stages including a small proscenium and black box. Regardless of when you visit, you are bound to find an assortment of high quality, intelligent plays. The tickets are cheap—$10–20 for students—and if you’re having a light quarter, it’s just $25 a month for unlimited admission. Bonus: Theater Wit is located on Belmont Avenue, a bustling commercial street that makes for a great afternoon of exploring. If you’re a tea lover, check out Pedestrian Coffee. They sell high quality looseleaf teas by weight, and you can sit and brew them yourself with gooseneck kettles. —Nolan Shaffer, Arts Editor
Bloomin’ Cherries: If you find yourself itching to explore Hyde Park on foot, Jackson Park’s Garden of the Phoenix is a great place to go. It’s a traditional Japanese garden in the heart of the South Side, originally established in 1893 for the Chicago World’s Fair. Just head west on the Midway to Jackson Park, and you’ll soon find this gem on Wooded Island. When you arrive, you’ll discover koi ponds, quaint bridges, small trails, and even a Yoko Ono sculpture. The garden is especially busy in the spring, when the island’s many cherry blossom trees bloom. —Jake Zucker, Podcasts Editor
Memento Mortifying: Next to a dry cleaner and across the street from a terrific Middle Eastern grocer in northern Andersonville lies Woolly Mammoth, an oddities shop not much bigger than a shoebox. It’s packed with unforgettable curiosities: 19th-century hair sculptures woven from the locks of lost loved ones; more than one taxidermy two-headed calf; piles of teeth; antique pornography; and an actual drawing by John Wayne Gacy (at least the last time I paid a visit). A museum for the curious and a gift shop for the depraved, Woolly Mammoth is not to be missed. Get there by the Red Line; the stop is Argyle. —Noah Glasgow, Lead Arts Editor
Jazzed Up: You don’t need to pay a cover—or be twenty-one, for that matter—to experience great jazz in Chicago. Every third Tuesday of the month, the Hyde Park Jazz Society (HPJS) presents Third Tuesday Jazz in Café Logan. Local jazz musicians are selected by the HPJS for the expansion and cultivation of jazz appreciation in the neighborhood. Notable performers include the Miguel De La Cerna Trio, the Ben Paterson Trio, and Fred Jackson Jr. The evening performance is punctuated with commentary from the highly experienced musicians and murmurs of appreciation from the audience—and the sense of community fostered by the highly intimate performances and friendly audience members is second to none. I heard the best live rendition of Ahmad Jamal’s “Poinciana” I’ve ever heard at Third Tuesday Jazz. Seats fill up quickly, so arrive early. —Elizabeth Eck, Senior Arts Reporter
Size Doesn’t Matter: Okay, this is kind of a cheat, but what makes Chicago’s theater scene so incredible is its breadth and depth. A ton of small companies—playing in their own 20–40 person venues or switching stages from show to show—put on great works by playwrights like Harold Pinter, Karl Čapek, and Sam Shepard alongside equally experimental contemporary fare. There’s a truly incredible range of shows going up in this city every night (I’ve had low schoolwork weeks where I reviewed three or four shows in a week) and these small, neighborhood theaters are where new artistic ideas develop. Plus, tickets are usually cheap, and the ambiance of a neighborhood theater lobby cannot be beat. In particular, check out City Lit Theater Company, Steep Theatre Company, Definition Theatre, Invictus Theater Company, Raven Theatre, and Three Crows Theatre Company, and keep your eyes peeled for Chicago Maroon reviews of great active shows! —Zachary Leiter, Maroon Deputy Managing Editor and former Arts Editor
