orchid show
Photograph: Courtesy Chicago Botanic Garden
Photograph: Courtesy Chicago Botanic Garden

The best things to do in Chicago this week

Find the very best things to do in Chicago this week, including cultural events, festivals and shows.

Jeffy Mai
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Looking for fun activities to do this week? You've come to the right place! Winter has arrived and with it, frigid temps, so find fun things to indoors. If you'd rather embrace the elements, there are also plenty of things to do outdoors, including ice skating, snowboarding and skiining, and sledding. There’s even more on our list below, so scroll through the roundup of the best things to do in Chicago this week and start planning your calendar.

RECOMMENDED: Discover the best things to do in Chicago this weekend

Time Out Market Chicago

Best events in Chicago this week

  • Things to do
  • Loop

The ninth annual Chopin in the City festival returns from February 21-March 2. The event features a diverse program of concerts inspired by Frederic Chopin’s music. It’ll take place at various venues across the city, including the Green Mill and the Polish Museum of America. Check here for the full schedule of performances.

  • Things to do

Find the perfect piece to complete your space at this inaugural expo dedicated to contemporary art. Browse paintings, sculptures and more from more than 40 artists, with styles ranging from impressionism to realism. Get a first look during a Champagne and wine preview on Friday night; shipping is available for all purchased art.

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  • Things to do
  • Loop

Just because Chicago Restaurant Week has ended doesn’t mean there aren’t still deals to be found. Andersonville celebrates its diverse and dynamic dining scene with special prix fixe menus at some of the neighborhood’s top eateries for lunch or dinner from February 21-March 2. Participating spots include Big Jones, Minyoli, Tanoshii, Uvae, Anteprima and more.

  • Things to do
  • West Loop

Come help us crown the best margarita in the city at Time Out Market Chicago on February 23. Chicago’s top restaurants and bars will compete to see who makes the best version of the cocktail, as voted on by you. The winner will receive a trophy, cash prize and bragging rights. Participants include Big Star, La Josie, Mi Tocaya Antojeria, Mercadito, La Luna, Bodega Taqueria y Tequila, Cantina Rosa, Lonesome Rose and more. Tickets are on sale now for $35.

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  • Things to do
  • River North

The Godfrey Hotel Chicago hosts its annual Charity Ball, this year in support of Los Angeles wildfire relief efforts. Celebrate under the stars while enjoying a Champagne bar, passed hors d’oeuvres, seafood towers, carving stations, live music and more. Proceeds will benefit World Central Kitchen and Pasadena Humane.

  • Things to do
  • West Loop

In honor of National Margarita Day, the Market is offering special margaritas all throughout the week of February 17, sponsored by Tromba Tequila. On February 22, celebrate the cocktail holiday with us from 1-4pm. We’ll have a live DJ spinning beats, a photo booth and Tromba samplings. And don’t forget about our Margarita Competition the following day, when some of the city’s best bars and mixologists will battle it out to see who makes the finest version, as voted on by you.

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  • Things to do
  • Festivals
  • Loop

Chicago Black Restaurant Week returns for its 10th year February 9-23. 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.

  • Things to do
  • Exhibitions
  • Suburbs
  • Recommended

Need a break from the monotonous sights of winter in Chicago? Head to the North Shore for the Chicago Botanic Garden's annual orchid show, where there are more than 10,000 vibrant blooms on display to brighten your day. This year's show is inspired by the beauty of India—you'll marvel at a floor-to-ceiling peacock and a towering banyan tree with cascading roots. Swing by on Saturdays and Sundays to shop for orchids of your own in a pop-up marketplace, or stay late on select Thursday and Friday nights to have a cocktail and fried goat cheese during Orchids After Hours.

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  • Things to do
  • Ice skating
  • Millennium Park
  • Recommended

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 $17–$23 if you need to rent a pair. The Ribbon stays open through March (weather permitting) and even offers hours on Thanksgiving Day, Christmas Eve, Christmas Day, New Year's Eve and New Year's Day.

  • Things to do
  • Loop

The classic whodunit board game comes to life with this new stage play based on the 1985 cult favorite film. Six strangers gather at Boddy Manor for an evening filled with twists, turns and a murder mystery. You'll be laughing and guessing until the very end.

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  • Things to do
  • Suburbs

On the last night of Frida Kahlo’s life, viewers of Frida…A Self Portrait are transported to La Casa Azul, the famous Mexican artist’s home. The one-woman production is written and performed by Vanessa Severo, and sees the artist reminisce about her life. Throughout the 75-minute play, Severo connects her own life’s experience to the famed artist’s, and explores Kahlo’s works, addiction, physical limitations and romances. The play is running at Writers Theatre, a non-profit theatre company, in suburban Glencoe.

  • Things to do
  • Lincoln Park

At a motel in the Mojave Desert, two lovers, or fools as the play would suggest, meet up and clash. With just three main cast members, Fool for Love is a haunting drama that explores the deeply complex relationship between the trio. The play was written in 1983 by noted playwright Sam Shepard, whose works also include A Lie of the Mind and Buried Child, for which he won the Pulitzer Prize for Drama in 1979.

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  • Things to do
  • Loop

Betrayal isn’t structured like a traditional play. The events move in reverse chronological order, showcasing the demise of an affair and going back in time as it occurred and ultimately to the beginning. The play stars Academy Award- and Emmy Award-winner Helen Hunt as Emma, who is having an affair with Jerry, her husband’s friend and coworker. Betrayal, which is playing at the Goodman Theatre, was first written by British playwright Harold Pinter in 1978.

  • Things to do
  • Suburbs

A musical based on the 2007 film of the same name, Waitress follows Jenna, a waitress at a cafe who’s in an abusive relationship with her husband, Earl. After becoming pregnant, Jenna starts an affair with her doctor and enters a pie-baking contest, hoping to win the grand prize in order to fund her escape.

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  • Things to do
  • Loop

The modern-day adaptation of Shakespeare’s Hamlet tells the story of Juicy, a young, queer Black man grappling with his identity at a backyard cookout. The Pulitzer Prize-winning and Tony-nominated play by James Ijames is playing at the Goodman Theatre through March.

  • Things to do
  • Hyde Park

There’s a good chance that you’ve heard of A Raisin in the Sun. If you’re a fan of theatre, maybe you’ve even seen it or read it. The play, written by Lorraine Hansberry, depicts the experience of a black family on Chicago’s South Side as they try to improve their financial circumstances after the death of the family’s patriarch. The plot deals with still-relevant issues, like housing discrimination and racism. A Raisin in the Sun is being performed at Court Theatre in Hyde Park, the professional theatre of the University of Chicago.

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  • Things to do
  • Rush & Division

During its original Broadway run in 2015, Fun Home won seven Tony Awards, including Best Musical, Best Original Score and Best Leading Actor in a Musical. Now, the award-winning musical has moved on from New York and is playing in Chicago during Chicago Theatre Week. Fun Home was based off of the graphic novel memoir of the same name written by Alison Bechdel. Both the novel and musical follow Bechdel as the writer comes of age: Bechdel’s experience of coming out as a lesbian and her relationship with her father, who was a closeted gay man.

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  • Things to do
  • Lincoln Park

The song “Three Little Birds” by Bob Marley and the Wailers is almost 50 years old but its enduring message lives on, most recently in the children’s musical Bob Marley’s Three Little Birds, which is playing at The Greenhouse Theatre Center. The reggae classic is just one of many Bob Marley hits featured in the production, which centers around Ziggy and his three avian friends. The musical is inspired by the children’s book Every Little Thing, written by Marley’s daughter Cedella.

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  • Things to do
  • Near North Side

There’s plenty of cold weather fun to be had on the Art Deco-inspired terrace at the Gwen Hotel, which offers curling lanes plus fire pits and hot cocktails so you can warm up between rounds. Heat lamps are set up around the perimeter to keep things toasty and you can also hang out with a group around one of the fire tables.

  • Things to do
  • Loop

Look out over Lake Michigan and Millennium Park from the glass atrium on top of the Chicago Athletic Association hotel. The outdoor terrace is accessible year round and features fire pits to keep you toasty while you sip drinks. Cindy’s is running an après ski-inspired pop-up, with classic cold weather cocktails and themed decorations that transport guests to a snowy mountain getaway, daily through February 28.

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  • Museums
  • Museum Campus

Escape the planet with exhibits about the first lunar missions, the solar system and more, plus immersive shows in the dome theater. The Doane Observatory is also home to the largest public telescope in the area, and gathers 7,000 times more light than the human eye. Every Wednesday, the Adler stays open late from 4pm-10pm so that folks can visit after work or school. And best of all, admission is free on those nights for Illinois residents.

  • Things to do
  • Hyde Park

The Griffin Museum of Science and Industry has debuted an exhibit dedicated to the science and technology behind the world’s longest-running film franchise, James Bond. Fans can check out 13 vehicles and over 90 additional artifacts, including the prototype jetpack used in Thunderball, an MI6 Retina Scanner from GoldenEye and the Parahawk snowmobile hybrid from The World Is Not Enough. You’ll also be able to step into a lab space inspired by “Q” and test your skills developing the perfect vehicle for spy activities, designing stunts and more.

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  • Comedy
  • Uptown
  • Recommended

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.

  • 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. The company's signature show is more unpredictable than ever these days, 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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