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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.

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Photograph: Aaron Bean via Upslash

The holiday spirit is palpable this weekend, with the debut of beloved Chicago Christmas events like Christkindlmarket, the skating rink at Millennium Park and "Christmas Around the World" at the Museum of Science and Industry. If you prefer to wait until after Thanksgiving to dive into holiday festivities, snag tickets to FKA Twigs at the Riviera or see a modern, Chicago-set take of Romeo and Juliet at Chicago Shakespeare Theater. Plus, there's still time to see the wildly popular Andy Warhol retrospective at the Art Institute, and Chicago record store Gramaphone celebrates 50 years of vinyl. Bundle up and check out the best things to do in Chicago this weekend.

RECOMMENDED: Full Chicago events calendar

Things to do this weekend in Chicago

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Photograph: Jaclyn Rivas
Shopping, Markets and fairs

Christkindlmarket

icon-location-pin Daley Plaza, Loop
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You haven't experienced the holidays in Chicago until you've stepped into this giant open-air market inspired by a similar seasonal tradition in Nuremberg, Germany. At Christkindlmarket, guests can shop handcrafted items like nutcrackers, cuckoo clocks, beer steins and glass ornaments. When hunger strikes, nibble on potato pancakes, hot pretzels, schnitzel, döner and chocolate-covered treats. And no trip to Christkindlmarket is complete without a steaming mug of Glühwein, a traditional hot spiced wine (there's also hot cocoa for the kids). The holiday market boasts three locations in Daley Plaza, Gallagher Way and Milwaukee, but the outpost in the Loop is its most popular iteration. When the weather is decent, the market is generally packed in the evenings, so stop by in the afternoon for a more plesant (and less-crowded) shopping and/or dining experience.

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MillenniumSkating.venue.jpg
Photograph: Patrick L. Pyszka
Things to do, Ice skating

Ice Skating in Millennium Park

icon-location-pin Millennium Park | Chicago, IL, Millennium Park
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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. The most popular time to hit the rink is in the evening, so show up earlier if you don't feel like waiting in line for your chance to slide around. Take advantage of free skating lessons on Fridays at 11am and Saturdays and Sundays at 9am. If it seems too warm to skate, call ahead—this rink is open through March 8, weather permitting.

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Photograph: Liz Lauren
Theater

Romeo and Juliet

icon-location-pin Chicago Shakespeare Theater, Streeterville
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Chicago Shakes artistic director Barbara Gaines sets her new take on Shakespeare’s star-crossed lovers in the hot Chicago summer of 2020. Presumably, that means that Edgar Miguel Sanchez and Brittany Bellizeare’s titular teens will spend most of their time browsing TikTok and stressing about the election.

Time Out says
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Gramaphone Records
Photograph: Jordan Avery
Music, Dance and electronic

Gramaphone 50: Steve “Silk” Hurley + Derrick Carter + Ron Trent + Michael Serafini

icon-location-pin Metro Chicago, Wrigleyville
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Opened in 1969 as a shop specializing in folk, blues and jazz albums, Gramaphone Records became an integral part of the house music scene in the ’80s, stocking music from genre pioneers like Larry Heard, Farley "Jackmaster" Funks and Frankie Knuckles. Red Bull Music Festival Chicago is celebrating Gramaphone's 50th anniversary with an all-star dance party at Metro and Smart Bar, featuring sets from Steve "Silk" Hurley, Derrick Carter, Ron Trent, Gramaphone's current owner Michael Serafini and a long list of Smart Bar residents. Show up to dance the night away to records that were probably purchased at the iconic shop with a checkered floor.

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Photograph: J.B. Spector
Things to do, Exhibitions

“Christmas Around the World”

icon-location-pin Museum of Science and Industry | Chicago, IL, Hyde Park
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Every year, the Museum of Science and Industry puts up its 45-foot-tall Grand Tree and surrounds the towering pine with more than 50 trees that represent Chicago's various communities and their respective holiday celebrations. Visitors can admire the 30,000 lights that cover the trees and stick around for the "snow" that falls from the rotunda every 30 minutes. During the weekend, live performances of holiday music fill the room, lending some additional seasonal cheer to your day at the museum.

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Photograph: Reed Carson
Theater

P.Y.G. or The Mis-Edumacation of Dorian Belle

icon-location-pin Broadway Armory Park, Edgewater
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In Tearrance Arvelle Chisholm’s TV-era update of George Bernard Shaw’s classic Pygmalion, a Canadian popstar looking to toughen up his brand finds two rappers willing to take the job. Lili-Anne Brown directs the Midwest premiere at Jackalope Theatre.

Time Out says
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Photograph: Liz Lauren
Theater, Drama

A Christmas Carol

icon-location-pin Goodman Theatre | Chicago, IL, Loop
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The Goodman Theatre’s annual holiday production of the Charles Dickens classic keeps its seasonal charm intact in its latest iteration. No bah humbugs here. Larry Yando returns for yet another outing as Ebenezer Scrooge, while director Henry Wishcamper guides the classic story of three spirits who confront Scrooge with the consequences of his miserly actions.

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Andy Warhol. Skull, 1976.
Photograph: © 2019 The Andy Warhol Foundation for the Visual Arts, Inc. / Artists Rights Society (ARS), New York.
Art, Contemporary art

“Andy Warhol—From A to B and Back Again”

icon-location-pin Art Institute of Chicago | Chicago, IL, Grant Park
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Arriving in the Midwest after drawing hordes in San Francisco and New York, this retrospective (the first to be organized by a U.S. institution since 1989) of Andy Warhol's career features more than 350 works for guests to explore. Instead of focusing on a specific era of his life, “From A to B and Back Again” accounts for the entire breadth of the Pop Art legend's output, from early illustrations that were commissioned for magazines to recolored portraits of celebrities that graced the cover of Interview magazine. While there are plenty of familiar pieces on display (a print of Marilyn Monroe, several Campbell's soup cans), there are also sections of the exhibit devoted to lesser-known aspects of Warhol's practice, including performance art, television and publishing. Filled with self-portraits, homages to vaunted brands and celebrations of fame, “From A to B and Back Again” accentuates the echoes of Warhol’s art in the contemporary world—and seeing so much of it one place only makes its prophetic themes that much clearer.

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Photograph: Unsplash
Music, Classical and opera

Dead Man Walking

icon-location-pin Civic Opera House | Chicago, IL, Loop
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Based on the acclaimed non-fiction book that inspired the 1995 film starring Susan Sarandon and Sean Penn, Dead Man Walking is a contemporary opera that explores the relationship between a death row inmate and the nun who becomes his spiritual advisor. Making its Chicago premiere at the Lyric Opera, this production is different than what you usually see onstage at the Civic Opera House: the lyrics are all in English, the show opens with a scene depicting sexual violence and the script is rife with explicit language. Think of it as an decidedly R-rated version of a night at the opera.

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Handmade Market Chicago at the Empty Bottle
Photograph: Courtesy Handmade Market Chicago
Shopping, Markets and fairs

Handmade Market Chicago

icon-location-pin Empty Bottle, Ukrainian Village
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Add some shopping to your Saturday morning brunch routine by visiting Handmade Market at the Empty Bottle before (or after) you feast at Bite Cafe. You can sip a mimosa, a Bloody Mary or a beer while checking out the wares of 30 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.

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Photograph: Christopher Semel
Theater

Sundown, Yellow Moon

icon-location-pin Raven Theatre, Edgewater
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With their father out of a job, twin sisters Joey (Diana Coates) and Ray (Liz Chidester) return home to try and keep their family in tune. Featuring music by the Bengsons, this Chicago premiere of Rachel Bond’s drama promises to keep those hot sticky summer vibes going well into fall.

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Nevermore Park
Photograph: Amy Lombard
Art, Installation

Nevermore Park

icon-location-pin 949 W 16th St, Lower West Side
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Best known for devising the characters of Flyboy and Lil Mama that grace walls throughout Chicago, local artist Hebru Brantley latest project is an immersive origin story for his most famous creations. Named after a fictional Chicago neighborhood, Nevermore Park takes visitors through 6,000 square feet of installation that begin in a traditional art gallery before quickly transitioning to fantastical environments that feature a crashed rocket ship, a Pullman train car and thick clouds of fog. Much of the pop-up serves as a celebration of the African-American culture that Brantley grew up with, featuring old issues of Jet and Ebony magazines as well as vintage stereo equipment playing some of his favorite songs. The experience lasts about an hour and ends with a chance to purchase some exclusive Flyboy and Lil Mama merch that will only be available during the pop-up's run. 

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Photograph: Fadeout Media
Theater

Grey House

icon-location-pin A Red Orchid Theatre, Old Town
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“I’ve seen this horror movie before,” declares Henry (Travis A. Knight) as he and his girlfriend, Max (Sadieh Rifai), stumble into a remote cabin in the woods after crashing their car on a snowy mountain pass. Little good that knowledge does him. Levi Holloway’s Grey House takes a classic fright-flick set-up and suffuses it with a singular sense of eeriness. The play sometimes stumbles when it tries to turn mood into action, but its indelible weirdness, aided by director Shade Murray’s creeptastic world-premiere production, glows through. Children’s games with brutal consequences, the sound of scratching from within the house’s walls, sudden blackouts with mysterious whispers: The titular grey house is a well and truly haunted place.

Time Out says
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Chicago Architecture Biennial
Photograph: Tom Harris
Things to do, Festivals

Chicago Architecture Biennial

icon-location-pin Chicago Cultural Center | Chicago, IL, Loop
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Every two years, Chicago becomes the center of the world of architecture and design during the Chicago Architecture Biennial. Taking place over the course of nearly four months, the programming encompasses exhibitions, installations, forums and more events that explore the state of modern architecture and urbanism. The Chicago Cultural Center serves as the event's hub, where visitors can explore a large model of a traditional Chicago worker’s cottage, experience a multi-channel video installation and learn about the architecture present in cities such as São Paulo, Vancouver and Johannesburg. Venues like the Jane Addams Hull-House Museum and the National Public Housing Museum also hosts Biennial programming, in addition to partner programs at a variety of local institutions. Find a complete list of events and happenings at the Chicago Architecture Biennial website.

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Queen!
Photograph: Erik Kommer
Nightlife, Alternative nightlife

Queen!

icon-location-pin Smart Bar, Wrigleyville
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In the city that served as the birthplace of house music, the weekly Queen! party carries on the genre's inclusive and subversive spirit. Tucked away in Smart Bar's subterranean confines, residents Derrick Carter, Michael Serafini and Garrett David spin deep grooves while drag performers strut across the foggy dance floor. For serious dance music fans, the trek across town to spend a night at Queen! is a pilgrimage worth making.

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Wesley Willis
Photograph: Courtesy Matthew Rachman Gallery
Art, Drawing

“Wesley Willis: City of Many Dreams”

icon-location-pin Matthew Rachman Gallery, River West/West Town
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Best known as a musician responsible for bizarre songs like "I Wupped Batman's Ass" and "Rock 'n' Roll McDonald's," South Side-native Wesley Willis was also an avid self-taught artist and could often be found roaming the city selling ink drawings of Chicago landmarks for $10 to $20. Matthew Rachman Gallery's exhibition of Willis' drawings are culled from the collection of architect Paul Young, who met Willis on the streets of Chinatown. "City of Many Dreams" also features sculptures created of Ricky Willis (Wesley's brother), an architectural historian who works with local nonprofit Project Onward.

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BlockMuseum.venue.jpg
Art, Pop art

“Pop América, 1965-1975”

icon-location-pin Mary & Leigh Block Museum of Art, Evanston
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While American and European Pop Art is well-known, works by Latin American artists don't often receive the same attention and reverence. “Pop América” showcases nearly 100 pieces employing the visual language of Pop Art that were created by artists in places like Argentina, Brazil, Colombia, Cuba, Mexico and Puerto Rico. Artists such as Antonio Dias, Rubens Gerchman, Hugo Rivera-Scott are represented in the exhibit via works that represent the social, political and cultural themes that were prevalent in Latin America in the ‘60s and ‘70s.

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Yayoi Kusama Infinity Mirror Room
Photograph: Courtesy wndr museum
Art, Installation

wndr museum

icon-location-pin 1130 W Monroe St, West Loop
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Step inside one of Japanese artist Yayoi Kusama's famous Infinity Mirror Rooms at this pop-up exhibition, which features installations that blend art and science. The latest "chapter" of wndr museum features a lineup of new installations (giving previous visitors a reason to come back), focusing on works that utilize technology. Among the new experiences are a room lined with LED walls that guests can "draw" on with water, a series of abstract shapes that guests can project images onto and an interactive dance station that replicates and manipulates your moves on a screen. You'll also find a two-story rainbow slide and murals by local artists Mac Blackout and Lauren Asta. The latest iteration of wndr museum will stick around for "limited, yet undetermined amount of time," so squeeze in a visit while the current batch of installations is on display.

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GreenMill.venue01.jpg
Photograph: Martha Williams
Comedy

The Paper Machete

icon-location-pin The Green Mill, Uptown
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This twice-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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Photograph: Mike Sause
Theater

Drunk Shakespeare Chicago

icon-location-pin The Lion Theatre, Loop
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This isn't your grandmother's Shakespeare. Five classically trained actors gather to perform a Shakespearean play. The twist? One of them got into the whiskey before the show. The four sober cast members attempt to keep the script on track as hilarity ensues.

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Wired to Wear, Museum of Science and Industry
Photograph: Jaclyn Rivas
Museums, Science and technology

“Wired to Wear”

icon-location-pin Museum of Science and Industry | Chicago, IL, Hyde Park
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Try on the next generation of wearable technology at this exhibition devoted to clothing and augmentations that improve upon the capabilities of the human body. You'll see more than 100 inventions on display, including a flying Jet Suit made by Gravity Industries, Nike’s self-lacing shoes from Back to the Future Part II and Dainese’s D-Air Racing Suit, which monitors the speed and position to determine if embedded air bags need to be deployed. Guests can also try on the SpiderSense Vest (which uses vibrations to allow you to feel your surroundings) or the Electric Dreams headset (which reads brainwaves and translates them into colored fiber optics lighting).

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Maxwell Street Market
Photograph: CC/Wikimedia Commons/Edsel Little
Shopping, Markets and fairs

Maxwell Street Market

icon-location-pin Maxwell Street Market, West Loop
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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 ocassional 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.

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Fantastic Bug Encounters!
Photograph: © Te Papa 2016
Museums, Natural history

“Fantastic Bug Encounters!”

icon-location-pin The Field Museum | Chicago, IL, Museum Campus
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There are far more bugs than humans on the planet, and the Field Museum's latest exhibition gives you an opportunity to learn more about the tiny, multi-legged creatures that largely go unnoticed in our day-to-day lives. “Fantastic Bug Encounters!” features larger-than-life models created by Weta Workshops (the folks behind the Lord of the Rings movies) that allow guests to see insects like bees and praying mantises in extreme detail. Interactive stations let you test your reflexes against those of a mantis, send origami butterflies into a wind tunnel and perform bug brain surgery. There's even a bug zoo where you'll be able to get your hands on a dozen live bug species.

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Miguel Cervantes and the Chicago cast of Hamilton
Theater, Musicals

Hamilton

icon-location-pin CIBC Theatre, Loop
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Let’s not mince words, since we’ve already spilled so many of them: Hamilton, writer-composer-lyricist Lin-Manuel Miranda’s biography of Alexander Hamilton as refracted through a hip-hop, pop and R&B lens, is a sprawling, stunning, singular achievement. By filtering the story of the American Experiment’s beginning into modern, meticulously rhymed vernacular and populating the stage with performers of color to play the likes of Hamilton, Washington, Jefferson and Madison, Miranda and his regular collaborators (director Thomas Kail, music supervisor Alex Lacamoire and choreographer Andy Blankenbuehler) make the founding fathers feel fresh and, miraculously, human. RECOMMENDED: Our complete guide to Hamilton Chicago Weeks out from the country’s naming its 45th president, Hamilton’s new Chicago company arrives to remind us our democracy has always been messy, political, personal, and worth fighting for. Kail and Blankenbuehler fill designer David Korins’s spare set—which suggests that, like the country, it’s still under construction—with movement as thrilling and dense as Miranda’s lyrics. (The few moments of stillness are also used to great counter effect.) The nearly all-new Chicago cast (ensemble member Emmy Raver-Lampman is the sole transfer) easily lives up to the originals while finding their own new moments and shades. Miguel Cervantes is a rather more grounded Hamilton than the more frenetic Miranda, who originated the role, but Cervantes conveys the man’s vital, fatal

Time Out says
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Art on theMART
Photograph: Joshua Brott
Art, Film and video

Art on theMART

icon-location-pin Merchandise Mart,
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Every night, a 25-story-tall video installation takes over the side of the Merchandise Mart, filling the building's historic facade with vibrant colors and moving images. Harnessing 34 digital projectors, the show features work by a rotating lineup of artists and is best viewed from Wacker Drive or the Riverwalk, between Wells and Orleans Streets. Art on theMART lights up the night Wednesday through Sunday, with projections beginning approximately 30 minutes after sunset.

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