15 Awesome Things to Do in Chicago This Weekend

Finish up January strong with speed dating, unlimited steaks and a theatrical tribute to Sufjan Stevens

January 26, 2024 6:21 am
Jersey Shore star Pauly D djing
Here's the situation: Pauly D is coming to Chicago this weekend.
Pauly D

We rifled through tons of events to choose these 15 excellent options to enjoy in the Windy City these next three days. Whether you’re looking to fill your free time with flower arranging, polar bear plunging or just dancing to the beats of Jersey Shore’s Pauly D, Chicago’s got something for you this weekend. 

Friday, January 26

Chicago Restaurant Week 

We’re still in the midst of Chicago Restaurant Week, with 400+ participating restaurants offering specials and deals. It’s impossible to hit them all, but why not try? Restaurant Week continues through February 4. 

Chicago Beefsteak at DANK Haus German American Cultural Center

Hey, you never need an excuse to dress up in your best suit and stuff your face with steak, but the annual Chicago Beefsteak dinner gives you a pretty good reason to. At this year’s annual event, Dr. Carol Himmels and her crew will be serving up endless steak, alongside an enormous open bar, live band and some new inductees into the esteemed Beefsteak Hall of Fame. Tickets start at $195 and are going fast. 

A group of people hanging out in a room
Date My Friend
Date My Friend

Date My Friend: A Single Mixer With a Twist at Guild Row

Dive headfirst into the dating pool with your best wing person by your side. At this unique speed-dating event, attendees bring a single buddy to help introduce each other and get the sparks flying with other singles. The hour-long event will be followed by a mixer. Tickets are $30. 

House of Burlesque at House of Blues

House of Burlesque returns to the House of Blues this weekend, with an intimate burlesque and variety show featuring artists Camille Leon, Chamilla Fox, Hot Tawdry, Muffy St. Clair and Vayda Rhinestone. The dress code is business casual, so be sure to break out your burlesque show-worthy blazer. General admission tickets are just $25. 

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Jersey Shore star Pauly D djing
Pauly D
Pauly D

Pauly D at TAO 

Your weekend deserves better than just gym, tan and laundry (#GTL forever). Jersey Shore’s very own Pauly D will be DJ-ing at Tao this Friday night. General admission is $50.

Band members on a stage performing dressed as cowboys with mutlti-colored strobe lights
Cosmic Country Showcase
Sarah Lasrson/Cosmic Country Showcase

Cosmic Country Showcase at Sleeping Village 

The always unique, always amazing space-themed Cosmic Country Showcase is back at Local Universe this Friday. The show combines laughs, music and a healthy dose of costumes for a truly memorable night. Friday’s show features New York performer Lizzie No. Tickets are $21.63.

Saturday, January 27 

People running into the ocean
Chicago Polar Bear Club
Chicago Polar Bear Club

Chicago Polar Bear Club Plunge at Oak Street Beach

Sure, cold plunges may be the talk of TikTok right now, but the Chicago Polar Bear Club has been ahead of the trend since 2002 — and has raised more than $650,000 to support Chicagoland families doing it. Join the Polar Bears this weekend as they run into the ice cold waters at Oak Street Beach, or just show up and show your support for a good cause. 

Beyonce Drag Brunch at Lark 

Whether you’re Crazy in Love with Beyonce or just know her most Irreplaceable hits, you’ll want to get in Formation for Beyonce Drag Brunch at Lark this weekend. Join drag queen Joan Jullian for an afternoon of music and costumes, and get Drunk in Love (or just buzzed on Mimosas and Bloody Mary’s) with the day’s bottomless drink specials. Reservations now open. 

Randy Rainbow at The Chicago Theatre

Randy Rainbow (yes, that’s his real name) has amassed a huge following over the years for his hilarious political takes and original show tunes. He’s hitting The Chicago Theatre this weekend on his “Randy Rainbow for President” tour (if only real presidential tours were this fun). Tickets start at $40. 

Hairbangers Ball at Joe’s Bar on Weed St.

One of Chicago’s most sought-after cover bands, Hairbangers Ball, heads to Joe’s Bar this weekend, playing the music of iconic groups like Guns N’ Roses, Mötley Crüe, Bon Jovi, Poison and more. (As if you needed another reason to break out your tight leather pants.) Tickets are $10.

Sunday, January 28 

Hyde Park Handmade Artisan Bazaar at Promontory Lounge

Some of the South Side’s best craft and food makers are gathering this weekend at Promontory Lounge for a monthly artisan bazaar. The event is free to enter, but with so many great makers, you definitely won’t leave empty-handed. 

Illinoise at Chicago Shakespeare 

Pay homage to Sufjan Stevens’s acclaimed album about our beautiful state. The musical theater-take on the album features a live band, unique stories and direction/choreography from Tony Award winner Justin Peck. The show starts this Sunday and runs through February 18, with tickets starting at $54. 

Roseology 101: Floral Arranging Class at The Bouqs Co Flower Studio 

Roses are red. Rosé is pink.

The Bouqs Co Flower Studio 

Is Giving You Both This Sunday

For Just $82 a Ticket. 

Okay fine, the rhyme may not be there, but the important highlights are. This Sunday, learn to make an Instagram-worthy rose bouquet while enjoying glasses of complimentary rosé. Both beginners and experts are welcome.  

Cider Aperitif at R Public House

Chicago Cider Week begins next week, but you can get a head start at R Public House’s pre-kickoff event. Cider Aperitif features small pours, canapés and fun. Registration is required and costs $38.


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