15+ Great Things to Do in Chicago This Weekend

Fill up your weekend with Valentine’s celebrations, the auto show and Super Bowl parties galore

February 9, 2024 6:15 am
My Funny Valentine Market
My Funny Valentine Market
Vintage House

What’s going on in Chicago this weekend? Well, between puppy speed dating, Chicago Theater Week, seemingly endless Super Bowl parties and so much more, the short answer is “just about everything.” Here’s our top picks for the weekend ahead. 

Friday, February 9 

Speed Friending at the International Museum of Surgical Science

Form new friendships over the antique x-rays machines, research skeletons and the other medical oddities at the International Museum of Surgical Science’s 2nd annual Speed Friending event this Friday. Looking for more than just friends? The Museum has you covered. Attendees will be provided wristbands to show if they’re looking to make friends, open to romantic connections or both. General admission is $50. 

Hearts and Daggers at MSA & Circus ARTS

Forget the dozen roses and heart-shaped boxes of chocolate. Instead, celebrate this Valentine’s Day with a romance-themed circus show, featuring incredible feats, international talent, interactive stations and themed cocktails. Tickets start at $60.30 and include two drinks.

Chicago Theater Week at Various Locations

Whether your taste in theater skews towards musicals, depressing Greek classics, Shakespeare but drunk or somewhere else entirely, Chicago Theater Week has something for you. Running now through February 17, you can catch shows across the Chicagoland area, with ticket prices ranging mostly between $15 and $30.

World of Chocolate at Union Station

Nothing against that leftover bag of fun-sized chocolate from Halloween that you’re still working through, but this Friday, you’ll have the opportunity to sample truly incredible chocolate from 15 of the city’s best chocolatiers and chefs. The event also includes an open bar, light bites and a punch board with mystery prizes, all for a good cause. General admission tickets are $175 and proceeds benefit the AIDS Foundation of Chicago. 

Puppy Speed Dating at Dovetail Brewery

Find your perfect puppy match at the Chicago Canine Rescue’s “Speed Dating” event at Dovetail Brewery. Spend time with adoptable puppies and snap a pic (or 300) in the puppy kissing booth, all while enjoying drinks, a raffle, vendors and crafts. The event is free to enter, and all proceeds from the raffle and $1 from every beer sale go towards supporting CCR. 

Saturday, February 10 

Valentine’s Day Taste Around at Eataly

Don’t quote us on this, but we’re pretty sure that Valentine’s Day was originally meant to be celebrated by eating homemade pasta directly out of a giant wheel of Parmigiano Reggiano. Regardless of traditions, at this Eataly event, attendees will have a chance to visit 10+ tasting stations while enjoying wine, cocktails and photo opportunities. Tickets are $55 and selling fast. 

Heart of Chicago Soul Club Valentine’s Day Party at Color Club

Chicago’s favorite all vinyl dance party is back this weekend at Color Club. DJs will be spinning vintage soul, R&B and psych music. Bring a date or have fun mingling on the dance floor. General admission is $14. 

The Most Romantic Restaurants in Chicago
First date, anniversary or no reason at all? Here’s where to book a table.

Paczki Class at Delightful Pastries

Paczki Day is next Tuesday (Feb. 13), but skip the bakery line this year and learn to make your very own this weekend with pastry chef Dobra. Attendees will learn to make dough and put in their own favorite fillings, plus they’ll have the chance to make angel wings (chrusciki) in the class as well. The class is $85. 

Vintage House Chicago Presents: My Funny Valentine, a Valentine’s Market at Rockwell on the River

Vintage House is bringing more than 125 vintage and handmade vendors to Rockwell on the River this weekend, making it the perfect time to snatch up some gifts for your Valentine (or, more importantly, for yourself). The event is free and runs on both Saturday and Sunday. 

Chicago Auto Show at McCormick Place

Whether you’re looking to leave the show with a brand new Lexus or just want to ogle hundreds of new and unique vehicles, there’s a place for you at the Chicago Auto Show. The largest auto show in the country returns this week, kicking off to the public on Saturday and running through February 19. An adult ticket is $17. 

Chicago Black Restaurant Week

Chicago Black Restaurant Week begins this Saturday, with specials at dozens of Black-owned restaurants across the Chicagoland area. Specials will be posted here. Get your Open Table reservations ready. 

Sunday, February 11 

Winemaking Experience Dinner and Dance at Wild Blossom Meadery

Admit it — you’ve always wanted to try out grape stomping. This weekend, that dream can finally come true at Wild Blossom Meadery. This unique event includes a grape stomping contest, dinner, a dance and the chance to make your own vat of wine. Tickets are $125 per person. 

Fika Fest at Andersonville

Once again, the Swedes have it all figured out — fika literally translates to “a coffee and cake break.” This weekend, Andersonville businesses are hosting their own fika moments with sales, specials and a puzzle exchange from 11 a.m to 3 p.m. at the Swedish-American Museum on Sunday. 

Y’All’s Brunch at Carol’s Pub 

Forget football — this Sunday afternoon, spend the day at Y’All’s Brunch at Carol’s Pub, a country-western inspired drag show, with entertainment, food, drinks, fun, laughs, prizes and performances by Chicago drag superstar Mini Pearl Necklace. 

Super Bowl Watch Parties: Our Top Picks 

It’s Super Bowl Sunday and, if we’ve been following the news stories correctly, Taylor Swift is going to be playing defense with the Kansas City Chiefs. Here’s an assortment of where in Chicago you can watch her tackle: 

  • Whirly Ball: Enjoy the Super Bowl and a few rounds of Whirly Ball while you’re at it. Chicago locations will have specials on wings, pretzel bites and beer buckets during the big game. 
  • Big Game Brunch at Cafe Ba-Ba-Reeba: Wear your jersey to watch the game at Cafe Ba-Ba-Reeba and win a gift card matching the value of your meal (excluding tax and gratuity) to redeem during a future visit. Touchdown. 
  • Puppy Bowl Viewing Party at The Cauldron Chicago: Finally, a chance to cheer on the real athletes, the stars of the Puppy Bowl. 
  • LG’s Bar and Kitchen: LG’s is offering a bevy of Super Bowl deals, including food and drink pitcher specials and the chance to win prizes like a Polaroid camera and a JBL speaker
  • Big Bowl Sunday Viewing Party at Time Out Market Chicago: Haymarket Brewery will be doing a pop-up at Time Out with select and specialty beers, plus a massive screen, giveaways and more. 
  • The Piggery Chicago: The Piggery is offering up a $70 open bar and dinner buffet. The hangover on Monday will be so worth it. 


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.