13 Awesome Things to Do in Chicago This Weekend

Spend your weekend enjoying a mac and cheese crawl, a ballroom dance competition and a nearly-naked run around Wrigleyville

February 23, 2024 6:07 am
two women holding mac and cheese and #macandcheesecrawl sign
Mac & Cheese Crawl at Wrigleyville

It may still be winter, but there are plenty of ways to enjoy yourself, both indoors and out. Take advantage of the rare spring-like weather this weekend with live comedy shows, a puzzle swap and a world class ballroom dance competition. Here are the best things to do in the city from Friday to Sunday.

Friday, February 23

Winter Open Dancesport Competition at Loews O’Hare Chicago

Whether you’re a dancing whiz or you’re still struggling to learn the Macarena, come watch some of the world’s top ballroom dancers compete this weekend at the Winter Open Dancesport Competition. Dancers from around the globe — including both amateur and professional — will compete in different divisions and styles. Tickets range in price from $25 to $150 and are available to the competition, seminars, dinners and the awards ceremony. The event runs all weekend. 

Sex and Exes at Color Club

Valentine’s Day, Schmalentine’s Day. At this storytelling and poetry event hosted by the Messy Misfits Club, it’s all about the messiness that comes with “sex, exes and maybe sex with your exes.” In addition to performances, there will be a range of vendors to shop. Tickets are $8. 

Improvised Sitcom at Second City

You could stay in and watch that episode of The Office you’ve seen 3,000 times before. Or, better yet, you could catch an entirely improvised episode of a made-up sitcom at the aptly named Improvised Sitcom at Second City’s Judy’s Beat Lounge. The show features a recurring cast of comedians who, based on an audience suggestion, make up a one-hour sitcom on the spot. Tickets are $25. 

Chicago Black Restaurant Week Continues

It’s the last weekend of Chicago Black Restaurant Week — don’t miss your chance to enjoy specials at dozens of Black-owned restaurants across the city and neighboring suburbs. Whether you’re looking to revisit an old favorite or discover a new go-to (or all of the above), check out participating restaurants in this interactive map.

The 15 Best Gyms in Chicago 
Whether you want an all-in-one athletic club or a niche boxing or cycling studio, we’ve got options

Saturday, February 24

Cupid’s Undie Run in Wrigleyville 

Sure, in Wrigleyville, it may not be all that unusual to see someone running down the street in their skivvies. But this weekend, people will be doing it for a good cause instead of doing it after a few too many Malört shots. Join the Cupid’s Undie Run for a “mile(ish)” jog in your best underwear to raise money for Neurofibromatosis (NF) Research. Since the run began in 2010, the community has raised more than $21,700,000. Registration to run is now open, or you can layer up and head over to watch. 

bridge and garden covered in snow
Malott Japanese Garden at the Chicago Botanic Garden
Chicago Botanic Garden

Winter Bird Walk at Chicago Botanic Garden 

Some of the toughest birds — like the true Chicagoans they are — don’t fly south for the winter. Instead, like us, they remain here to battle out the cold, forage for food and, presumably, call dibs on parking spots. Pay homage to them this weekend at the Chicago Botanic Garden’s Winter Bird Walk, which will be led by Alan Anderson of the Chicago Audubon Society. Tickets are $27, BYOB binoculars and field guide. Can’t commit to an 8 a.m. Saturday event? The Chicago Botanic Garden’s Orchid Show of Wonders is happening through March 25 and is well worth a (later-in-the-day) stop. 

Winter Wellness Workshops at Artifact Events

Slipping in your lofty 2024 wellness goals? Come to this day of workshops, vendors, freebies, movement classes, vision boarding, cold plunging and more to get back on track. A $40 general admission ticket covers classes, vendors and vision boarding. Additional workshops are extra. 

If You Know, You Know: A Celebration of Chicago Black Comedians at Annoyance

It’s the last night to catch If You Know, You Know, a variety show series hosted by Stepping Stone Theater in collaboration with the Annoyance Theater. The show celebrates the city’s Black comedians, with new talent each week from across the Chicago community. Tickets are $15. 

Mac and Cheese Crawl at Wrigleyville 

Push your lactose tolerance level to the absolute limit at the Mac and Cheese Crawl, where attendees will sample seven servings of mac and cheese from across Wrigleyville establishments. Tickets purchased before February 24 are $10 and also include drink specials, giveaways and more. 

Sunday, February 25 

Global Connections International Carnivale at Navy Pier

Celebrate Carnivale traditions from around the globe at the Aon Grand Ballroom, with art-making activities, music, food and dance. The event will also feature performances representing traditions from Brazil, Colombia, Jamaica, Puerto Rico, Greece and more. The event is free with food and beverages available for purchase. 

Beatles Brunch with Phil Angotti and Friends at City Winery 

Get by with a little help from Peter Angotti and Friends, with a brunch celebrating that little indie band The Beatles. Peter Angotti is a Chicago-based multi-instrumentalist, singer and songwriter, known across the city as “THE Beatles Guy.” Tickets start at $15, with a brunch buffet add-on available for $25. 

Yoga Flow and Brunch at KitchnStudio

You’d be hard pressed to find a more iconic Sunday morning pairing than the KitchnStudio yoga and brunch. The event features an all-skill level yoga flow session taught by Jacoby Daniels of Hilltop Yoga Chicago, followed by a curated brunch cooked by the KitchnStudio team with a complimentary Mimosa. Tickets are available starting at $33.75, including both the class and brunch. 

Ravenswood Puzzle Swap at Falcon’s Handcrafted Sandwiches

Refresh your winter puzzle routine, thanks to the Greater Ravenswood Chamber of Commerce. Bring in a new or gently used 500+ piece puzzle to exchange for another, all while enjoying free coffee and Mexican bread. There will also be an on-site sign up for Chicago Public Library cards. The event is free, but those who RSVP ahead of time will be entered to win a Malt Row puzzle. 


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