The best February 2025 events in Chicago

Calling all sweets lovers! Chef and chocolatier Jorge Kauam offers an irresistible selection of specialty handmade confections—including the viral Dubai chocolate bar—at the Market on weekends. Stop by to indulge your sweet tooth but don't wait as the pop-up will only be around for a limited time!

Bingo Loco, an interactive rave show that takes place in cities around the world, comes to West Loop’s Morgan MFG this winter. The traditional game of bingo gets reimagined as a three-hour long immersive experience, complete with epic dance offs, rave rounds, lip sync battles, confetti showers, CO2 cannons, conga lines and prizes ranging from international trips to lawnmowers. One thing’s for sure—this ain’t bingo night at the senior center.

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.

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.

After you’ve learned the basics at Sip & Script’s introduction to modern calligraphy workshop, take the next step with an intermediate level class. Experts will help level up your skills by teaching how to mix your own colored ink, the fundamentals of lettering design and basic flourishing composition. All materials will be provided, and everything will be yours to keep at the end of the evening.

The North Side is bringing back its own Restaurant Week, offering exclusive deals during lunch and dinner. Enjoy three-course menus at places throughout Lincoln Square, Ravenswood, Albany Park, Edgewater, Irving Park, Northcenter, North Park, Rogers Park and Uptown. Participating spots include Maman Zari, Bistro Campagne, Khmai, Boonie's, Luella's, the Warbler and more. Find the full list of restaurants and menus here.

This annual fundraiser that supports those affected by cancer takes over Sarabande for an evening of fun and entertainment. Enjoy an exciting blend of food and beverages, interactive experiences like flash tattoos and tarot readings, and live entertainment. This year’s event benefits the Chicago Foundation for Women, which empowers women, girls and gender-expansive individuals in the Chicago region.

The northwestern suburbs of Roselle, Schaumburg, Arlington Heights, Elk Grove Village, Itasca, Rolling Meadows, Streamwood and Wood Dale will showcase their culinary scenes with 10 days of dining specials. Dozens of restaurants—from steakhouses to quick-service spots—will offer set menus or deals during lunch and dinner. Participants include Chicago Prime Italian, Tokio Pub, Shaw's Crab House, Capital Grille and more. Check out the full list here.

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.

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.

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.

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.

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.

You’ve probably seen Hamlet. Now it’s time to see Fat Ham, a reimagining of the Shakespeare tale. The Pulitzer Prize-winning and Tony-nominated play by James Ijames tells the story of Juicy, a queer Black man whose widowed mother has married his uncle. When his father’s spirit shows up for revenge during a backyard cookout, Juicy must grapple with his identity. Fat Ham is showing at the Owen Theatre, part of the Goodman Theatre in the Loop.

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.

Sam Shepard is one of the most highly-regarded American playwrights for good reason—his works are a masterclass in writing about bleak situations and infusing them with black comedy, like in A Lie of the Mind. The play, which is also a part of Chicago Theatre Week at the Raven Theatre, is centered around spousal abuse and how it impacted two families.

Some of the Chicago Theatre Week offerings are only available to see for a short time, but that’s not the case for The Infinite Wrench—the longest-running late-night show in Chicago. The performance is actually 30 different brief plays, all packed into one hour. Even if you’ve seen The Infinite Wrench before, you’re still in for a treat as the plays change weekly.

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.

You’ve probably seen a Shakespeare play before, but never like this. Five professional actors come together for each performance of Drunk Shakespeare. The twist? One of them has had five shots before the show and is trying to stay on track while the other four actors do their best to hold the performance together.

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.

The Griffin Museum of Science and Industry has dedicated an exhibit to the science and technology behind the world’s longest-running film franchise, James Bond. Fans of the renowned secret agent 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.

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 pops up inside The Robey on select Sundays from December through March. Browse goods from more than 15 local, rotating vendors like Donutistry, Hook Point Fisheries and The Love U Collective—and you can always grab a coffee from Cafe Robey to sip on while you stock up.

The South Loop Farmers Market heads indoors for the season, bringing more than 75 vendors each Sunday to the fourth level of Water Tower Place. Shop for fresh produce, preserved veggies, cheeses, meats and more while enjoying live entertainment. Guests can also check out a kids' play zone, capture special moments with family and pet photography, and play some virtual reality games.

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.

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.

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.