16 Great Things to Do in Chicago This Weekend

Spend your weekend enjoying live music, Martinis and the annual Lunar New Year parade

February 16, 2024 6:51 am
Cocktails in a row on a countertop
Cocktails from Ramova
Clayton Hauck

Those Netflix reruns can wait until next week. Instead, fill up your weekend with everything Chicago has to offer, including a Chance the Rapper concert, the Auto Show and the chance to do yoga in a distillery. Here are 16 top-notch happenings to keep you busy this weekend.

Friday, February 16

Neon sign for the Ramova theatre
Clayton Hauck

Chance the Rapper at Ramova Theatre

A few things are true for nearly every Chicagoan — we’re not above calling dibs on a parking spot in February, we’re going to make fun of you (at least a little) if you put ketchup on your hot dog and we all have a sense of pride for Chicago’s own Chance the Rapper. The hitmaker is performing his new show “B-Sides and Seasides,” which combines art, music and cinematography. Plus, this is a great chance to see the Ramova Theatre, which recently reopened after a years-long, multi-million dollar rehabilitation. Tickets are $99. 

People lined up on a stage in front of a TV playing instruments
Makeout Party
Makeout Party

The Makeout Party at The Hideout

Get your Burt’s Bees chapstick ready because the annual Makeout Party is back this weekend at the Hideout. The space will be all decked out with high school prom decorations, freshly cut roses and a rotating roster of 30+ musicians bringing you a bevy of music, ranging from Herb Alpert-inspired arrangements to ’70s soul songs. The event is also running on Saturday. Tickets are $20. 

Valentine’s Martini Cocktail Class at Lost Never Found

Still searching for the city’s perfect Dirty Martini? Take matters into your own hands this weekend at Lost Never Found, where you’ll have the chance to step up your own mixology skills and learn to make three classic Martinis. The event will also feature a pizza bar. Tickets are $55. 

People dancing in a crowd in front of a stage with singers and band members. There are strobe and disco lights across the room.
Tickled Pink
Cancer Wellness Magazine

Tickled Pink Fundraiser at Rockwell on the River

More than 20 of Chicago’s top chefs and restaurants are coming together this Friday to raise money for Twist Out Cancer, a nonprofit that provides psychosocial support to cancer previvors, survivors and caregivers through creative arts programming. The event will also feature live music, a raffle and it’s a chance to get all dressed up in your best cocktail attire. Tickets are $125. 

People sitting at high top table in bar area
Lincoln Lodge
Sarah Larson Photography

Main Stage Show at Lincoln Lodge

Spend your Saturday night at one of the city’s consistently great stand-up comedy shows. The Main Stage show features the Lincoln Lodge’s all-star cast, plus additional appearances from top comics from around the country. (Bonus: while the theater does offer a bar, there’s no drink minimum to attend.) Tickets are $15. 

Chicago Auto Show at McCormick Place

Forget the rusted hunk of junk that’s constantly parked on your street — this weekend, see cars as they were meant to be seen at the Chicago Auto Show. The show features a wide variety of vehicles, ranging from sensible sedans to seven-figure luxury cars. The event runs through February 19 and an adult ticket is $17. 

Chicago Black Restaurant Week

Chicago Black Restaurant Week continues this weekend, where you can enjoy specials at dozens of Black-owned restaurants across the Chicagoland area. Check out participating restaurants and maybe discover a new neighborhood favorite in this interactive map

Saturday, February 17 

Jonathan Van Ness at the Vic Theater

Queer Eye’s own Jonathan Van Ness is playing two shows at the Vic Theater this weekend and — while you may not have the chance to ask them about the Bobby versus Tan drama — you will get to hear them perform stand-up comedy, which is (nearly) just as fun. Tickets start at $80. 

Chicago Bacon Fest at Old Crow Smokehouse

Ten out of 10 doctors agree — the average American isn’t getting nearly enough bacon in their diet. Luckily, the folks at Old Crow Smokehouse are here to remedy that this weekend. Chicago Bacon Fest features a bacon-focused food menu (including bacon meatballs with bacon marinara, bacon-glazed vanilla churros and much more), plus bacon cocktails, bacon photo opps and so much more. GA tickets are $10 and include a cocktail and a shot. 

8 Black-Owned Restaurants in Chicago to Try, Stat
From a spot serving up four-course alligator dinners to quite possibly the best taco stand in the city

Cupid’s Vintage Fest at The Patio Theater

Vintage shopping is great for a bevy of reasons — it’s sustainable, affordable and it gives you the chance to smugly tell people, “thanks, it’s vintage” when you’re inevitably complimented on your awesome wardrobe. This weekend, Windy City Market is bringing 100+ vendors to the Patio Theater on both Saturday and Sunday. RSVP ahead of time for free admission. 

Malinalli Garden Workshop Series: Mercado Bag Customization at the National Museum of Mexican Art 

Louis Vuitton will be quaking in his boots once he sees your design skills at the NMMA’s Mercado Bag Customization Workshop this weekend. Tickets include everything you need to make the Mercado Bag of your dreams, plus proceeds go towards supporting the museum’s workshops and Yollocalli youth programming. Tickets are $150.

2024 Chinese New Year Dumpling Making Dinner at Hing Kee Restaurant 

Welcome the Year of the Dragon with Hing Kee Restaurant, where you’ll have the chance to learn dumpling making while you feast on a wide variety of Chinese foods and witness a Chinese lion dance performance. An adult ticket is $50. 

Sunday, February 18 

Chicago Wine Fest at Hubbard Inn

Whether you have your sommelier certification or still consider anything other than Two-Buck Chuck the height of luxury, there’s something for you at the Chicago Wine Fest this weekend. Your $35 ticket includes 15 tastings, covering a wide range of wines. 

Alex Edelman’s “Just for Us” at Steppenwolf Theatre

Alex Edelman is at the Steppenwolf this weekend with a meaningful show that’s also been described as “belly laugh funny” by The New York Times. The show follows Edelman, who covertly attends a meeting of White Nationalists in Queens, where he comes face-to-face with the people who have been bullying him online. Tickets start at $72 and the show runs through Feb. 24. 

Chicago Chinatown Lunar New Year Parade

Chinatown’s annual Lunar New Year Parade is this Sunday and will feature traditional dragon and lion dancing teams, floats, marching bands and other groups. Kick off the Year of the Dragon with a celebration like no other. The parade begins at 1 p.m. at the intersection of 24th Street and Wentworth Avenue.

Yoga and Cocktails at Koval Distillery

Finally, exercising the way it was meant to be done — with a few cocktails after. This yoga class will take place on the distillery platform, and participants can stick around afterwards to enjoy a sampling of drinks, with full-sized cocktails available for purchase at the bar. Tickets are $25. 


Join America's Fastest Growing Spirits Newsletter THE SPILL. Unlock all the reviews, recipes and revelry — and get 15% off award-winning La Tierra de Acre Mezcal.