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The Play that Goes Wrong
Photograph: Jeremy Daniel

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.

Zach Long
Written by
Zach Long
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The weather outside is still somewhat frightful (not to mention slippery), so we've gathered plenty of indoor things to do in Chicago this weekend. If you're craving live music, you can catch local retro rocker Neal Francis at Thalia Hall or head to the South Loop for a bluesy set during the Buddy Guy residency—just a couple of the best January concerts in Chicago. If you'd rather look at art and artifacts, museum exhibitions like the “Andrea Bowers” show at the Museum of Contemporary Art might be more your speed. And if you just can't wait for Chicago Theatre Week, you can see The Play That Goes Wrong or Disney's Frozent this weekend. Try to stay warm as you experience some of the best things to do in Chicago this weekend.

RECOMMENDED: The best things to do in Chicago right now

Things to do this weekend in Chicago

  • Art
  • Photography
  • Suburbs

More than 20 years after her untimely death, Princess Diana has once again entered the realm of public obsession thanks to new media like Netflix's The Crown, a Broadway show called Diana: The Musical and the upcoming movie Spencer starring Kristen Stewart. Chicago fans will have yet another way to learn about the life of the iconic princess starting this December, when a traveling exhibition of images and stories chronicling Diana's life lands at the suburban Oakbrook Center mall. 

"Princess Diana Exhibition: Accredited Access" showcases photographs from royal photographer Anwar Hussein and his two sons, Zak and Samir—who collectively spent more than four decades photographing Diana and her family—alongside art, murals, artifacts and rarely-told stories from the Hussein family that provide behind-the-scenes context to the photos. The exhibition is broken up into eight themed sections with topics ranging from "glam" to "unguarded," aiming to capture a comprehensive look at Diana's life. Along the way, art installations from multimedia artist Pauline Loctin depict interpretations of Diana's most famous moments. And of course, at the end of the tour, visitors can stop by the exhibition store to grab Diana-themed merch. 

  • Music
  • Folk, country and blues
  • Loop

Most people call January "the first month of the year" or "four weeks of taking my resolutions seriously," but Chicago blues fans know that it's actually "Buddy Guy month." Throughout the month, the legendary bluesman picks up his polka-dot guitar and takes the stage during a residency at the South Loop blues clubs that bears his name.

Guy performs every Thursday, Friday, Saturday and Sunday night, with a different supporting act joining him each evening. This year, you'll see Guy paired with folks like local singer Demetria Taylor, California guitarist Leilani Kilgore amd veteran singer-songwriter John Primer. Tickets to Guy's January residency aren't exactly cheap, but witnessing a bonafide blues icon perform in his hometown is the kind of experience that's worth the dough.

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  • Art
  • Contemporary art
  • Streeterville

Tackling issues like immigration rights, workers’ rights, climate justice and women’s rights, the work of Los Angeles artist Andrea Bowers is nearly always imbued with a message. Her latest exhibition at the Museum of Contemporary Art assembles a collection of work that documents decades of activism, including a Radical Feminist Pirate Ship Tree-Sitting Platform and a video piece that features Indigenous rights activists fighting against the Dakota Access Pipeline project.

  • Art
  • Painting
  • Loop

The Chicago Cultural Center hosts the first comprehensive retrospective of Robert Colescott, a 20th century American painter whose incisive, large-scale work took aim at racial inequities in America—among other social ills—with humor and wit. The exhibition examines Colescott's work throughout the decades, moving through the artist's stylistic evolutions from riffs on the Bay Area Figuration of the '50s and '60s to his graphic style of the '70s and beyond, as well as his role in bolstering Black representation in art.  

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  • Theater
  • Musicals
  • Loop

Disney's latest Broadway adaptation comes to Chicago, bringing the smash-hit animated movie Frozen to life in front of your eyes. Adapting the contemporary fairy tale about a princess with frigid magical powers, the stage version comes complete with all the songs you (and any kids you know) are already familiar with, including the inescapable earworm, "Let It Go." Settle in for powerful anthems, spectacular special effects and strange human-manipulated versions of Olaf the snowman and Sven the reindeer.

  • 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. This year's edition of the ribbon will be decorated with designs inspired by Vincent van Gogh's "Sunflowers" and "Starry Night" paintings, a collaboration between the art exhibition "Immersive Van Gogh" and Chicago Park District. 

Admission to the Skating Ribbon is free during weekdays if you bring your own skates; otherwise, reservations are $5 (with skates on weekends on holidays) or $16–$20 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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  • Time Out Market
  • West Loop

Every Sunday from 11am to 3pm, Time Out Market Chicago's chefs offer a variety of delicious brunch dishes, from Hangover Ramen with shrimp and smoked pork to a stack of Buttermilk Pancakes layered with whipped mascarpone. Order as much as you want, grab a mimosa pitcher from the bar and stick around from 1 to 3pm for a set of tunes from the Chicago Soul Jazz Collective. 

  • Theater
  • Comedy
  • Streeterville

If the sight of onstage failure (purposeful, in this case) doesn't make you cringe too much, then you're probably the target audience for this unique play-within-a-play. Following a troupe of amateur performers that are presenting a production of a fictional murder mystery, this comedy does exactly what its name implies. From flubbed lines to inadvertent destruction of the set, you'll see all your worst theatrical nightmares come to life before your eyes—in the name of laughter!

Review of 2018 staging:

The animating principle behind The Play That Goes Wrong, the scrappy British meta-comedy turned transatlantic hit, is that bad drama—if bad enough—can function as good comedy. Presented as a performance of the fictional whodunit The Murder at Haversham Manor by the amateur Cornley University Drama Society, the play takes Murphy’s Law to an exponential degree. Everything goes wrong, then wronger, then wrongest; even Nigel Hook’s set, a delightful contraption of self-destruction, seems eager to get in on the action.

The show’s play-within-a-play is a dusty Agatha Christie knockoff brimming with stock characters who boomingly declaring their intentions and secrets. Charles Haversham (Yaegel T. Welch) of Haversham Manor is dead, and a detective (Evan Alexander Smith) has been called to solve the case; the suspects include Haversham’s fiancée (Jamie Ann Romero), brother (Ned Noyes), butler (Scott Cote) and future brother-in-law (Peyton Crim). As the actors muddle through their parts, abetted and thwarted by their sound and light operator (Brandon J. Ellis) and stage manager (Angela Grovey), their commitment to the show-must-go-on ethos rarely falters, even when everything else is collapsing around them.  

Written by the trio of Henry Lewis, Jonathan Sayer and Henry Shields, The Play That Goes Wrong is as subtle as its title. The comedy is relentlessly broad—a challenge to sustain in a play that lasts nearly two and a half hours. While the zaniness always manages to top itself eventually, aided by director Matt DiCarlo’s dynamite cast, there are sizeable stretches where it gets stuck in place. It’s not that the jokes aren’t funny, it’s that they’re hurled at such a steady pace that they tend to run together. Still, the guffaws keep rolling in, much to the chagrin of Chris Bean (Smith), the director/designer/everything-else behind The Murder at Haversham Manor, who admonishes the audience for laughing at his handiwork. Alas, he’s out of luck: His awful drama has spoiled into a very fine comedy indeed.

Oriental Theatre. By Henry Lewis, Jonathan Sayer and Henry Shields. Directed by Matt DiCarlo. Original Broadway direction by Mark Bell. With ensemble cast. Running time: 2hrs 20mins. One intermission.

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  • Sports and fitness

Hit the ice at the Chicago Wolves Ice Rink at Rosemont's Parkway Bank Park, where you can reserve a free 45-minute skating session every day through December (including holidays); the rink will also be open on Sundays through February. Use of the rink itself is free—with skate rentals available for $8—but you'll need a credit card to hold your reservation online. 

  • Things to do
  • Festivals
  • Wrigleyville

The Cubs may be hibernating for the winter, but Gallagher Way provides some excellent reasons to hang out in Wrigleyville during baseball's off-season. The Wrigley Field-adjacent space hosts a variety of seasonal activities, including the Wrigleyville outpost of Christkindlmarket, an ice skating rink, photos with Santa and holiday movie screenings on every Wednesday in December. Opening on November 19, you'll be able to shop for gifts, sip glühwein and enjoy delicious treats through the end of the year. Once the holidays are over, the skating rink at Winterland will stick around through February 20. Visit the Winterland website for reservations, hours and additional information about programming.

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  • Art
  • Old Town

Step inside of Starry Night and The Bedroom in Arles with the help of more than 50 digital projectors in this high-tech exhibition that explores the work of Vincent Van Gogh. Designed by the Italian creative team that worked on the "Atelier des Lumières" exhibitions in Paris, "Immersive Van Gogh" covers 35-foot walls with animated versions of the Dutch painters work, accompanied by a score that blends electronic and classical compositions.

The show takes up residence in the Germania Club Building in Old Town, which will go by the name Lighthouse ArtSpace Chicago and host additional interactive art exhibitions in the coming years. Occupying four rooms in the space, the "Immersive Van Gogh" presentation is around 35-minutes in length, with mostly-identical projections displayed in each of the rooms throughout the show.

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  • Theater
  • Lincoln Park

Previewing November 24 and opening December 5 for a limited engagement, When Harry Met Rehab is based loosely on the real-life experiences of Chicago sports radio personality, Harry Teinowitz. When Harry Met Rehab is an evening in the theater that will leave a mark that is flat-out funny, moving, and unforgettable. It is a story of redemption, perseverance, and hope. It is estimated that over 22 million Americans are in recovery. This show is for them, their families, and their friends.

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  • Things to do
  • Exhibitions
  • Magnificent Mile

Calling all The Office fanatics: The same team that created "The Friends Experience" is back with another nostalgic pop-culture experience that will make you feel like a Dunder Mifflin employee. Spread across two floors, the pop-up features 17 rooms that recreate sets from the show, including the Scranton Business Park workplace (which features Michael's office, Pam's reception desk and Ryan's closet) and Schrute Farms. Guests will be able to ecreate moments like Kevin's chili spill and the Dundie Awards—and you'll also find a few original props and costumes on display.

Don't forget to stop by a gift shop that's dressed up like the Warehouse, featuring merch like "World's Best Boss" mugs, sweatshirts that say "Nard Dog" and staplers (Jello not included). The gift shop will be open to both ticketed and non-ticketed guests, so even those who don't spring for the photo-friendly experience have a chance to buy some branded shirts and tchotchkes.

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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. Admission to the rink is free, and you can rent skates for $13–$15. Plus, take advantage of free skating lessons on most Saturdays and Sundays from 8am–9am, 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 6, weather permitting.

  • Museums
  • Natural history
  • Museum Campus

Explore the colors of the natural world in the Field Museum's latest exhibition, which examines the meaning and function of some of the brightest hues in the world. “Wild Color” explores how plants and animals use color to ward off predators or attract maters, and how the color of gems and minerals can offer clues about their formation. The 7,000-square-foot exhibition is filled with specimens from the Field Museum's extensive collection, including a platypus that fluoresces under UV light and birds in every color (including "super black").

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  • Art
  • Mixed media
  • Suburbs

A deft collage artist who has created pieces for Lou Reed and Steve Earle as well as public installation in CTA stations, Tony Fitzpatrick is hosting his final museum exhibition. While he's not putting down his paintbrush for good, "Jesus of Western Avenue" offers one last chance to see a new collection of multimedia works by the artist, with more than 60 new creations on display. Presented by the Cleve Carney Museum of Art on the College of DuPage campus, the exhibit is housed not far from where Fitzpatrick began making art, acting and writing poetry. 

  • Museums
  • Music
  • Near South Side

A musician who introduced traditional Indian styles of music and instruments to Western audiences, Ravi Shankar earned the title of "the Godfather of world music" from George Harrison of the Beatles. This exhibition at the South Asia Institute examines his career and the impact he had on popular culture, assembling more than 100 items, including rare concert posters, photographs, videos, record covers and personal ephemera. Guests can explore the collection, listen to the sitarist's music and gain a deeper appretiation for Shankar's creative output as well as his influence on the likes of Phillip Glass and John Coltrane.

The South Asia Institute will offer free admission to the exhibition every Friday.

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  • Museums
  • History
  • Skokie

Tracing the contemporary gay rights movement back to the June 1969 police raid of the Stonewall Inn in New York City, the Illinois Holocaust Museum's hosts an exhibtion that documents a continuing struggle for equality. On loan from the Newseum, “Rise Up: Stonewall and the LGBTQ Rights Movement,” collects more than 85 artifacts, such as posters from Harvey Milk’s campaign for public office in San Francisco and the gavel Nancy Pelosi used to announce the repeal of “don’t ask, don’t tell.” Visitors will learn about the history of the LGBTQ community through pivitol moments in history and in popular culture.

  • Art
  • Photography

Explore the small-but-mighty works of photographer André Kertész, who arrived in Paris in the fall of 1925 with a camera and what was left of his savings. Over the next three years, the majority of the photos he produced were printed on postcard paper, making them easy to share with friends and benefactors. Exhibiting a collection of these small-scale works, the Art Institute's latest exhibit explores Kertész's output in the years before he graduated to international exhibitions and magazine spreads.

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  • Art
  • Photography
  • Loop

There are more guns than people in America, making it the most heavily-armed country in the world. “American Epidemic: Guns in the United States” collects photos from 10 different photographers that contemplate the violence, trauma, racism and other issues that arrise in a society where shootings are commonplace. You'll find images by Carolyn Drake, Nancy Floyd, Stephen Foster, Andres Gonzalez, Félix González-Torres, Deborah Luster, Zora J Murff, Renée Stout, and Hank Willis Thomas and Kambui Olujimi in the exhibit. If you're going to visit, make sure to secure a timed reservation via the Museum of Contemporary Photography's website. 

  • Theater
  • Loop

Rick Bayless’s latest theatrical creation is an immersive show that’s accompanied by a tasting menu (six bites, one small cocktail and two pours of wine), staged in a space beneath Petterino’s that’s dressed up to look like a fictitious restaurant called The Contumacious Pig. Written by Bayless, Windy City Playhouse artistic director Amy Rubenstein and local playwright Carl Menninger, A Recipe For Disaster casts the audience as attendees at a restaurant’s “influencer night,” where mishaps abound as the staff attempts to impress the Instagramming masses.

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  • 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.

  • Art
  • Contemporary art
  • Grant Park

Don't call this one a retrospective. Yes, the Art Institute's exhibition of Barbara Kruger's work encompasses four decades of her career, but "THINKING OF YOU. I MEAN ME. I MEAN YOU." isn't stuck in the past. Instead, the display takes Kruger's vintage works and presents it alongside new pieces that build upon them, unlocking new context and meaning. Spread throughout the museum, guests will find rooms wrapped in Kruger's imagery, installations in the Regenstein galleries and pieces that inhabit the exterior walls of the museum (as well as billboards, bus stops and storefronts around Chicago). Expect to see Kruger's biting sense of humor on display—often spelled out in big, bold letters.

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  • Comedy
  • Stand-up
  • Logan Square

Now housed in the space on Milwaukee Avenue in Logan Square, the country's longest countinuously running independent comedy showcase continues every Friday and Saturday night. Boasting alumni like Cameron Esposito, Kumail Nanjiani and Hanibal Buress, this stand-up show will introduce you to fresh new faces that may end up starring in Marvel movies or becoming podcast mainstays. Snag an affordable ticket, avoid the two-drink minimum and prepare to laugh your ass off.

  • Art
  • Contemporary art
  • Streeterville

The Museum of Contemporary Art Chicago presents a survey that encapsulates two decades of work by Pakistani artist Bani Abidi, a former student at the School of the Art Institute of Chicago. Known for her video, photography and sound works, Abidi satirizes displays of power and nationalism as she explores the geopolitical relationship between India and Pakistan as well as the historical power struggles of South Asia. The exhibit takes its name from Abidi's watercolor series "The Man Who Talked Until He Disappeared," which depicts writers, political leaders and bloggers from Pakistan that have disappeared over the past decade.

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  • Theater
  • Experimental
  • Lake View

Since 1997, a trio of performers covered in bright blue paint have headlined the Briar Street Theater in Lakeview. The Blue Man Group's show has evolved throughout the years, incorporating new compositions, narratives and state-of-the-art technology. But at its core, this production is all about combining percussion, music, physical comedy and buckets of brightly-colored paint in ways that make you want to jump out of your seat and dance along to the beat.

  • 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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  • Shopping
  • Markets and fairs
  • West Loop

Originally established in the late 1800s, the Maxwell Street Market brought vendors, musicians and cooks to an open-air flea market where shoppers could find just about anything they wanted. The market introduced the Maxwell Street Polish sausage, provided a venue for rising Chicago blues musicians and was immortalized in a scene in The Blues Brothers. These days, the market sets up on nearby Desplaines Street (between Roosevelt and Howard) every Sunday, where visitors will find vendors hawking their wares, an abundance of delicious Mexican food and occasional performances by local bands and dance troupes. Don't let the cold or wet weather scare you away—the Maxwell Street Market takes place outdoors year-round.

  • Sports and fitness
  • Running

Go for a run and replentish your electrolytes with a beer during this series of 5K walks and runs, that take place at breweries throughout Chicago (and beyond). All of the Illinois Brewery Running Series events are untimed fun runs, more focused on camaraderie than competition. Participants at each event recieve a free beer, glassware or seasonal swag item, plus access to post-run events that feature live music, food, goodies from sponsors and giveaways. Check out the complete schedule of events on the Illinois Brewery Running Series website.

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  • Art
  • Sculpture
  • Suburbs

See five 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 five of the sculptures along the way.

  • Art
  • Photography
  • Lincoln Park

The Chicago History Museum welcomes a fascinating multimedia exhibition of more than 65 pieces from the celebrated street photographer. Known for beautifully capturing everyday moments, each of the shots on display here was taken when Maier was a suburban Chicago nanny from the ‘50s to the ’70s. Most of them have never been on display, and feature alongside film clips, quotations, and sound bites that help to bring Maier’s incredible work further to life.

‘Vivian Maier: in Color’ opens May 8 2021. Admission is included in the Chicago History Museum entry price. For more information head to www.chicagohistory.org/exhibition/vivian-maier-in-color

Written by Time Out. Paid for by Chicago History Museum

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