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The best things to do in Chicago this weekend

Find the best things to do in Chicago this weekend with our guide to concerts, exhibitions, festivals and more.

Jeffy Mai
Edited by
Jeffy Mai
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Welcome to another weekend! Take a load off by checking out the Chicago Auto Show or a folk festival. There are also tons of special events planned for Valentine's Day and the Super Bowl. And foodies can take advantage of some great deals during Chicago Black Restaurant Week. So ready to make the most of your time off? Check out the rest of the best things to do in Chicago this weekend. 

RECOMMENDED: The best things to do in Chicago right now

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Events and to do this weekend in Chicago

  • Music
  • Folk, country and blues
  • Hyde Park

The 63rd annual University of Chicago Folk Festival is back in person for 2023. Attendees will enjoy seven bands from a variety of genres, including blues, bluegrass, Bulgarian folk, Irish folk and more. Tickets are $30 for general admission, $20 for seniors and $5 for students.

  • Things to do
  • Conventions
  • Museum Campus

The Chicago Auto Show—the largest car show in North America—is headed back to McCormick Place for 10 days this February to showcase the latest and greatest developments in the world of cars, trucks, electric cars and concept cars. Manufacturers trot out their newest models in elaborate exhibitions, often accompanied by interactive installations that allow you to get behind the wheel (whether physically via indoor/outdoor test track or virtually).

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  • Things to do
  • Festivals
  • Loop

Chicago Black Restaurant Week returns for its eighth year on February 12. Created by Lauren Smith as a way to highlight and support local Black-owned businesses, the annual event sees participating eateries offer special menus and discounts to diners. This year’s lineup includes CheSa’s Bistro, Bronzeville Soul, Taste 222 and more.

  • Things to do
  • Wicker Park

Don’t care about football? Then join the Den Theatre for the Puppy Bowl instead. You’ll be able to watch little pups on the big screen and enjoy mimosas and Bloody Marys from the bar all afternoon. There will also be a complimentary brunch buffet as well as activities for children. A portion of the proceeds will go to the Anti-Cruelty Society to help rescue, shelter and foster animals.

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  • Things to do
  • Lincoln Square

It’s still cold out but you can escape to the isles of Greece for a bit this weekend by heading to St. Demetrios Greek Orthodox Church for Winter Greekfest. The three-day event will include lots of authentic Greek fare and spirits plus live music and dancing. Free parking will be available at Swedish Hospital.

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  • Things to do
  • Lower West Side

Presented by Chicago Vintage Fest, Cocktails With Cupid at Thalia Hall will showcase 20 vintage and handmade vendors. Guests will also be able to sip on Valentine’s-themed concoctions and take a picture with cupid. Entry is free; RSVP here.

  • Bars
  • West Loop

Singles, get ready to shake off your relationship woes at a Taylor Swift-themed pop-up coming to the West Loop next month. Bad Blood, a breakup bar named after the eponymous single from the singer’s album 1989, will launch February 3 at Electric Garden and run through February 26. There will be tarot card readings, photo ops and a Shake It Off wheel that guests can spin for themed cocktails.

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  • Theater
  • Millennium Park

Loosely inspired by the popular opera The Barber of Seville and its iconic aria "Largo al factotum,” this new production at the Harris Theater follows brothers Mike and Garby as they clash over the future of their family’s barbershop on Chicago’s South Side. The Factotum blends classical singing with diverse musical styles to create a soul opera, shifting from gospel and funk to rap and hip-hop to classic barbershop quartet and R&B.

  • Things to do

Stroll through Edgewater Chamber of Commerce’s Winter Bryn Mawrkets, where you can peruse stellar work by makers from all over the windy city from wellness to apparel. Don’t miss the one-of-a-kind art installations and purchase art to take home at the Winter Bryn Mawrkets Gallery. Check out their website for the full list of local vendors you'll find there.

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  • Shopping
  • Markets and fairs
  • Ukrainian Village

Add some shopping to your Saturday morning brunch routine by visiting Handmade Market at the Empty Bottle. You can sip a mimosa while checking out the wares of local vendors selling funky jewelry, clothing, handbags and paper crafts. You probably need a gift for someone—or yourself—right? Handmade Market takes over the Bottle on the second Saturday of the month from October through April.

  • Shopping
  • Markets and fairs
  • Wicker Park

Chicago farmers market season is well past its peak, but you can still get in on the fresh produce action during this winter edition of the Wicker Park market, which is popping up inside The Robey’s lobby on select Sundays from December through April. Browse goods from vendors like River Valley Ranch, Star Farm and Zeitlins Delicatessen—and you can always grab a coffee from The Robey’s espresso bar to sip while you stock up. 

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  • Art
  • Contemporary art
  • Streeterville

What does “Caribbean art” look like? This new group exhibition at the Museum of Contemporary Art takes a diasporic approach to answering that question, using weather—and all its changeability and unpredictability—as a metaphor for exploring artistic practices and identity-making within Caribbean art communities across the world. With the tumultuous geopolitical climate of the 1990s as its backdrop, the exhibit highlights work from 37 international artists; it’s also the first major MCA exhibitiobn to presented in both Spanish and English. 

  • Things to do
  • Ice skating
  • Millennium Park

Situated in the heart of downtown Chicago with the city's sweeping skyline as a backdrop, the Skating Ribbon at Maggie Daley Park is a winter attraction unlike any other. Skaters can lace up and wind around a winding ice-covered path that's twice the length of a lap around a traditional rink. Reservations for the popular ice rink should be made in advance, as they tend to fill up quickly.

Admission to the Skating Ribbon is free Monday through Thursday and for 11am sessions Friday through Sunday (and $5 for other time slots Friday through Sunday, as well as holidays) if you bring your own skates. No skates? Entry is $16–$22 if you need to rent a pair. The Ribbon stays open through March (weather permitting) and even offers limited hours on Thanksgiving Day, Christmas Eve, Christmas Day, New Year's Eve and New Year's Day.

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  • Things to do
  • Ice skating
  • Millennium Park

Skate under the Chicago skyline and within eyeshot of the Chicago Christmas Tree at the McCormick Tribune Ice Rink in Millennium Park. Plus, take advantage of free skating lessons on most Saturdays and Sundays from 9–10am, where you can learn both beginner- and intermediate-level skills. Note that you'll need to make a free online reservation for both regular skating and lessons this year, and if it seems too warm to skate, call ahead—this rink is open through March 5, weather permitting.

  • Things to do
  • Exhibitions
  • Streeterville

Yer a wizard, Harry! Or at least, you can pretend to be one at this immersive Harry Potter experience that’s popping up at Water Tower Place through May 2023. Visitors are invited to step into Harry’s life at Hogwarts with interactive features like Quidditch lessons, Charms and Defense Against the Dark Arts classes, sipping sweet drinks at the Butterbeer Bar, Patronus-seeking in the Forbidden Forest and learning their Hogwarts house via the Sorting Hat, among other magical experiences. FYI: In addition to regular operating hours, the exhibition is open on “select” Tuesdays and Wednesdays and may offer different hours around holidays. 

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  • Museums
  • Science and technology
  • Hyde Park

Tap into feelings of childhood nostalgia at the Museum of Science and Industry’s newest exhibit, a colorful glimpse into the world of Mold-A-Rama™ machines. Explore a collection of popular, rare and experimental souvenirs, learn about the history of the machines’ production and breathe in the iconic scent of their plastic toymaking—you can even take home a few new Mold-A-Rama™ souvenirs if you’re looking to expand your collection. 

  • Museums
  • Natural history
  • Museum Campus

Delve into the often-mystifying process of death in this surprisingly life-affirming exhibit at the Field Museum, which explores dying through a variety of natural and cultural processes. Attendees can explore highlights like a full-sized ofrenda made by Chicago artist Norma Rios-Sierra, a replica of a whale's body on the ocean floor and check out a variety of interactive media and soundscapes to help ponder some of life's big questions about death. 

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  • Art
  • Arts centers
  • Humboldt Park

Working in partnership with the Museo de Arte de Ponce in Puerto Rico, the National Museum of Puerto Rican Arts & Culture is bringing a stunning selection of paintings to Chicago—some of which have never been shown outside of Puerto Rico—for an exhibition highlighting several of the island's most important artists. Centered around three curatorial themes (“My Home,” “My People” and “My Island”), the works span from the 18th century to the first half of the 20th century, showcasing artists like José Campeche, Francisco Oller, Miguel Pou and Myrna Báez, among others. Tickets to the exhibition are free, but you might consider a small online donation to the Museo de Arte de Ponce, which is still recovering from damage sustained in a 2020 earthquake.  

  • Comedy
  • Sketch shows
  • Lake View

Bye Bye Liver combines two robust Chicago traditions: comedy and heavy drinking. The show opened a decade ago for a three-week run, then kept getting extended. A cast of four to six performers portray characters at the fictional "Franks Bar," telling stories that explore the city's robust drinking culture. Each show incorporates interactive audience drinking games, allowing you to sip a cocktail or beer while taking cues from the cast. And if you're up for a nightcap after the performance, you can stick around for the official after party and mingle with the cast.

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  • Nightlife
  • Cabaret and burlesque

Settle in for an evening of burlesque performers, belly dancers, drag artists and variety entertainers during this weekly show at Newport Theater. The hour-long show features speciality cocktails and intimate seating arrangements, making this feel like a clandestine speakeasy experience. Bring some singles so that you can tip performers throughout the night!

  • Theater
  • Experimental
  • Uptown

For more than 30-years, the Neo-Futurists have been delighting late-night crowds with performances that pack 30 miniature plays into a 60-minute show. Returning to in-person programming (attendees must be vaccinated and masked) after more than a year spent in the virtual realm, the company's signature show is more unpredictable than ever, with a handful of compact new plays premiering every week. Within the span of 10 minutes, you may be treated to a poignant monologue about everyday life or an irreverent diatribe delivered by a pantsless member of the cast—all inspired by the experiences of the performers on stage. Always changing and evolving, it's the rare show that truly offers something different everytime you show up to see it.

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  • Comedy
  • Uptown

This weekly “live magazine” is a cavalcade of culture, politics and wit featuring journalists, actors, comedians and musicians offering idiosyncratic reports on the news of the day. Head to Uptown’s iconic Green Mill for drinks, hot takes and laughs; the longstanding Saturday afternoon edition tends to run about two and a half hours.

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  • Art
  • Sculpture
  • Suburbs

See eight towering sculptures by South African artist Daniel Popper at the Morton Arboretum's new outdoor exhibition, which spreads the 15- to 26-foot-tall works throughout the natural area. Made of glass-reinforced concrete, wood, fiberglass and steel, the one-of-a-kind pieces in "Human+Nature" depict human figures that evoke the natural landscape they're set amid, including a pair of 36-foot-long hands reaching out from a grove of oak trees and a maternal figure that springs up amid magnolia trees.

Access to "Human+Nature" is included as part of timed-entry admission to the Morton Arboretum, and there's a map that will allow you to easily plan your visit and spot all eight sculptures along the way.

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