13 Great Things to Do in Chicago This Weekend 

Kick off January with concerts, comedy and reality tv

January 5, 2024 6:56 am
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Comedy is never a bad idea.
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We’ve made it out of the holiday stupor and into January, so don’t waste your weekend sleeping off that lingering eggnog hangover. Instead, kick off the first full weekend of 2024 with secret concerts, film festivals and a tribute to David Bowie himself. Here are 13 great things to do in Chicago this weekend. 

Friday, January 5

Wonder City Rooftop Ice Skating Experience 

Whether you’ve perfected your triple axel jump or can’t make it 10 feet on the ice without falling, it’s the last weekend to ice skate under the Chicago skyline at Wonder City. The experience also includes curling lanes, a hockey slap shot station and more. The 2026 Winter Olympics are calling your name. Adult skating passes start at $22.99.

Yacht Rock Experience at City Winery

We’re still about six months away from needing to find a friend with a boat, but it’s always the right time for Yacht Rock. The Docksiders take the stage at City Winery with the sounds of Hall and Oates, Christopher Cross, Air Supply and more. Tickets start at $18, but the opportunity to finally dust off that Hawaiian shirt from the back of your closet is free.

SoFar Sounds Concert at Goose Island 

SoFar Sounds is back, with an intimate show at a unique venue at Goose Island. You’ll get a text 36(ish) hours beforehand with the location and artist, but one thing that’s not a mystery is you’ll have a great time. Tickets start at $26. 

DeMar DeRozan Chicago Bulls v Philadelphia 76ers
DeMar DeRozan and the Bulls take on the Charlotte Hornets at home on Friday.
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Charlotte Hornets at the Chicago Bulls 

According to that one guy at work, 2024 is definitely going to be the Bulls’ year. Get a head start on cheering them on this weekend, as the Bulls take on the Charlotte Hornets. Tickets start at $53. 

Where to Eat in Downtown Chicago Right Now
If you’re not hungry yet, you will be soon

Saturday, January 6

Hitchcock and Friends Festival at the Music Box 

The Music Box is screening films by Alfred Hitchcock and the directors that drew inspiration from him all month long. This weekend, see Charade, the Audrey Hepburn and Cary Grant classic. (And for your post-movie plans, grab a drink and discuss the film at the great Music Box Lounge next door.) General admission is $10. 

Dry January Mocktail Class at Eataly

Taking part in Dry January doesn’t have to mean 31 days of seltzer water and flat Diet Cokes. Instead, join Seedlip for a class that will teach you to create three unique mocktails, with a smattering of seasonal antipasti served alongside. Tickets are $45. 

Mariah Carey Christmas Drag Brunch at the Walnut Room

Hey, we all know the rule — the holiday season isn’t technically over until Queen of Christmas Mariah Carey says it is. This weekend, Chicago drag superstars will be paying homage to Mariah in the still decked-out Walnut Room. Christmas attire is encouraged, so don’t pack away those ugly sweaters just yet. Tickets start at $20. 

Paper Machete at The Green Mill

Spend your Saturday afternoon laughing and learning at Paper Machete, the weekly live magazine show at the legendary Green Mill, Al Capone’s former haunt. (And, if the Chicago ghost tours are to be believed, his gang’s current haunt, too.) Free. 

Bowie’s Ball at Metro 

Celebrate David Bowie’s birthday with drag and burlesque performances, a special club Bowie DJ set, glitter cocktails and much more. Ziggy Stardust-style face paint not required (but definitely encouraged). Advanced tickets for $15. 

Sunday, January 7

Wellness on the Water Winter Workout Series at Offshore Rooftop

Offshore Rooftop continues their Winter Workout Series this Sunday with a fitness class followed by a brunch buffet, wine and swag bags. If only every gym made working out this fun. (Your move, Planet Fitness.) Tickets are $55. 

Butterfly Pinning Workshop at The Insect Asylum 

Make 2024 the year you turn into a budding entomologist — or at least the year you make a unique piece of art for your walls. The Insect Asylum is hosting a Butterfly Pinning Workshop with hands-on practice alongside experts. The class is $45. 

A Night of Vanderpump Rules: Premier Party at Good Company 

Celebrate the return of Scandoval alongside other Vanderpump Rules fans at Good Company, where you can watch the premier, compete in trivia and get all fired up in a post-show discussion. BYOB, and your ticket also includes a non-alcoholic welcome drink and snacks. Tickets are $40. 

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Sautéed Stand-Up Tournament of Champions at Lincoln Lodge 

Chicago’s premier comedy cooking competition kicks off the Tournament of Champions this weekend. Check out some of the city’s top stand-ups as they try to wow a panel of professional chef judges with their cooking skills and their jokes. Tickets start at $12. 


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