While love is in the air this weekend, your plans definitely won’t be. Keep scrolling for weekend happenings, and a galore of date night plans.

You might have heard by now that singer-songwriter Mac DeMarco is coming to The Salt Shed on May 7th. You might have also heard by now that it’s been sold out for a hot sec. Well, if you didn’t get tickets while they were still available, don’t worry, we’re giving away a pair for absolutely free. Wanna win ‘em?

JUST ANNOUNCED

• Salt, sip, repeat. Margarita Fest is serving up endless margaritas with bold flavors and a party that never ends. Enter to win tickets and cheers to Chicago’s ultimate margaritaville. Bottoms up!*

• The Goodman Theatre is back with another show that’ll tug at your heartstrings. The Brief Wondrous Life of Oscar Wao, adapted from the Pulitzer-winning novel, is coming to Chicago for its world-premiere English stage adaptation from February 21st through April 5th. Grab your tickets now.*

• Live from Chicago, it’s Saturday night! Weekend Update co-star Michael Che is cracking jokes at The Hideout from April 16th through April 18th. If you love the SNL star, don’t miss this.

• Now at Avli River North: Gardenista. Fresh, restaurant-inspired cocktails, bottled and ready to pour. Make a rezzy.*

• Cortland’s Garage hosts Winter Bar Tournaments, brought to you by Do312 and Michelob ULTRA on February 18th, with classic bar games, killer prizes, and more! RSVP for a surprise.*

• Plus other just announced shows from Noah Kahan, Hillary Duff, Lupe Fiasco, Chiddy Bang, Jimmy Eat World, Sinkane, Carin Leon, Shrek Rave, Moonchild, Sarah McLachlan, Holly Humberstone, Trippin Billies, and more!

FREE STUFF TO DO IN CHICAGO

All the fun, none of the cost. If you’re looking for fun weekend plans that won’t break the bank, we’ve curated a whole separate calendar just for you. Check out some of our favorite free things to do around Chicago.

• TON.-TOM. - INK FEST 2026 at COLUMBIA COLLEGE

• TON. - FOR THE LOVE OF LOCAL SIP & SHOP at A. FAVORITE DESIGN

• TOM. - HOUSE VS. REGGAETON DANCE PARTY at SIMONE’S

• TOM. - SATURDAY NIGHT KARAOKE at DANTE’S TAVERN

• SUN. - ANTI-LOVE TRIVIA at SLEEPING VILLAGE

• EVERY SUN - SUNDAY BUNDAY PARTY at CELL BLOCK

COMING UP

LOCALS ONLY

• Gay on Valentine’s Day in Chicago? Us too! (Shocker, I’m sure.) Whether you’re spending the day with your girls or are taking out that special someone, here are some amazing ways to have a queer-a$$ V-Day.

• Mardi Gras is just around the corner on February 17th, and if you’re staying at home, you’re doing it all wrong. Start exploring Mardi Gras events around Chicago with our ever-growing list of parties, shows, restaurant specials, and more!

• You know what's more romantic than flowers that die in 5 days? 🌹 Two tickets every month to live concerts, comedy shows, and events — all year long. DoMORE annual membership is $50 this Valentine's Day only. That's 12 months of date nights, delivered instantly each month. Sign up now.

• Come work with us. It’s the best job ever. We’re not biased, promise. Apply now. 

WIN STUFF

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