The best things to do in Chicago this weekend

A winter tradition that's just as enjoyable as ice skating in Maggie Daley Park or standing under the heat lamps on CTA platforms, the annual Chicago Psych Fest brings a lineup of trippy bands to the Hideout. For the 15th anniversary, Flying Luttenbachers and Bronze will headline, joined by Bobby Conn, Head, To Is and James Marlon Magas, and more.

The Museum of Science and Industry hosts the annual Uncorked Wine Festival, where guests can enjoy more than 100 wines, Champagnes and nonalcoholic offerings as well as a variety of exhibitions and experiences. Spring for a VIP ticket to get an extra hour of tastings and a $30 food voucher, plus access to a private lounge with higher end wineries.

Love sausages and beer? Then join Haymarket for its annual Sausagefest, where guests can sample a variety of encased meats and craft brews. Guest sausage makers and brewers will be paired up to compete for people’s choice awards—as voted on by you.

Marz Community Brewing hosts a showcase of Chicago’s electronic music scene from March 7-15. Live performances will be held at both of Marz’s taprooms (McKinley Park and Logan Square), and there will also be a synth flea market featuring vendors and manufacturers selling gear. Admission is free; check out the full lineup here.

In its 23rd year, Chicago's annual Flamenco Festival brings a four-week-long lineup of flamenco's brightest young stars and critically acclaimed artists to the Instituto Cervantes of Chicago. Throughout the festival, flamenco performances, workshops, lectures, films and other events will be offered. Whether you're a novice or expert on flamenco, come celebrate some of the finest Spanish and Hispanic heritage in the city. 

Best known for his turn on Parks and Recreation and the romantic Netflix series Master of None, Aziz Ansari brings his new tour, the Hypothetical Tour, to town for two shows at the Chicago Theatre. After some time out of the spotlight, Ansari is ready to return to stand-up and will also direct and star in the comedy film Good Fortune alongside Keanu Reeves and Seth Rogan later this year.

Whether you're looking for love or just want to test the waters, join us for an evening of speed dating hosted by MyCheekyDate. Participants will be able to see all of their potential matches through a mobile scorecard and choose who they’d like to be paired with. Casual and comfortable, it’s the perfect way to mingle, laugh and maybe find that special connection.

Whether you consider yourself an oenophile or a novice wine drinker, there will be something new for you to discover during Chicago Wine Fest at Hubbard Inn. Gather some friends and sample 15 vinos while also enjoying live tunes, good vibes, giveaways and more.

Bring the little ones to the Market on March 8 for a donut decorating class. 2d Restaurant will teach young chefs how to unleash their creativity on three special mochi donuts with a variety of toppings and sprinkles. All of the necessary ingredients will be provided, and kids will be able to take their delicious sweet treats home.

On the first Friday of every month in 2025, join Eataly for a culinary adventure. Guests can enjoy five tastings at counters throughout the marketplace, including fresh pasta, Roman-style pizza, housemade pasticcini, artisanal salumi and formaggi, and more.

Celebrate 10 influential women in West Loop history on this four-mile, guided run with Read & Run Chicago for International Women's Day. Inspired by Connie Fairbanks's book Chicago's West Loop Then and Now, the tour will focus on West Loop’s earliest residents and the modern-day women who shaped one of the most famous neighborhoods in the U.S. After the route, recover with snacks and activities at Madison Street Books.

Looking for a fun way to celebrate St. Patrick’s Day with the little ones? Join the Market for an hour of musical storytime with local author Laura Bityou Beriau (@mommymomsbookshelf) and musician Ray Hogan (Mr. Ray). The pair have teamed up to curate an unforgettable experience filled with song, dance and classic Irish tales. Guests can also purchase books signed by Beriau to take home.

The JCC Chicago Jewish Film Festival returns for its 12th year, featuring 19 documentaries, dramas and comedies from around the world that explore Jewish identity and experience. Spread across three weeks, the showings will take place at Wayfarer Theater in Highland Park and the Illinois Holocaust Museum & Education Center in Skokie. This year's lineup includes Midas Man, a film that showcases the legendary career of Beatles manager Brian Epstein, and October H8te, which explores the explosion of anti-Semitism on college campuses, on social media and in the streets of America in the aftermath of October 7.

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.

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.

Hunt for rare treasures at a vintage pop-up shop at the Market. Browse through a unique selection of home decor, jewelry, clothing, accessories and much more from local vendors, and refuel afterwards with a delicious bite or drink at the bar.

Feast on specials from restaurants like Athena Restaurant (free saganaki with any entree order), 9 Muses Bar & Grill (50% off Greek wine and complimentary trio of spreads) and more during Greektown Restaurant Week, when diners can take advantage of discounts from some of the neighborhood's most beloved eateries. Visit Greektown's website to see a full list of participating restaurants and remember to mention Greektown Restaurant Week when ordering!

It’s Rosemont’s turn to get in on the Restaurant Week action. The suburban village kicks off its week of deals on March 2 and diners will be able to enjoy three-course prix fixe lunch or dinner menus at a variety of participating spots. Participating restaurants include Bub City, Carmine’s, Truluck’s, Morton's and more. You can check out the full list and menus here.

Winter is almost over and the Garfield Park Conservatory is here to usher in warmer days with its annnual Spring Flower Show. Make a reservation to explore this year's theme, "Rooted in Mystery," which explores the critical part of plants we don't see hidden underground. You'll find spring bulbs like azaleas, pansies, snapdragons, astilbe, baptisia, hydrangeas and more. The show only sticks around through Mother's Day weekend, so book your visit soon!

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.

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 November through April.

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.

Check out galleries and artistic spaces around Wicker Park and Bucktown during this free monthly event that takes place the first Friday of each month. Venues will keep their doors open until 8pm so guests can meet gallery owners and artists, and explore a range of local art. Participating spots include Jackson Junge Gallery, Tom Robinson Gallery, SoNa Contemporary Art, Torque Ltd., Prism Spaces and more.

Explore a host of galleries and programming at this monthly event that showcases West Town’s dynamic arts community. Galleries will stay open until 8pm.

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.

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.

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 is centered around spousal abuse and how it impacted two families.

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.

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.

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.

Head to 360 Chicago on Saturdays for yoga with a killer view. Instructor Britta Eumann will lead an hour-long class on the 94th floor of 875 N Michigan Avenue (formerly the John Hancock Center) that’s suitable for all ages and skill levels—you just need to bring your own mat and arrived properly dressed. Registration is $55 and includes a cocktail or coffee, plus admission to the observation deck so you can stick around and snap some photos after you're done striking poses on the mat.

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.

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.