5 Things to do this Weekend: February 14

Explore exciting events across Chicagoland this winter… from music and community celebrations to wellness and more! With so many opportunities to enjoy the season, here are a few of our top picks to check out this weekend.

Toast to Winter at the Chicago Winter Tequila Tasting Festival

Raise a glass to all things agave at this tequila lover’s dream event. Sample over 20 craft and small-batch tequilas and mezcals while brand ambassadors guide you through the tasting experience. With live DJ music, exclusive food and drink specials, and giveaways—including free tickets to future events—this festival is more than just a sip; it’s a full-on celebration.

Date: February 15 
Time: 2:30PM-6PM  
Cost: $24+ 
Location: Welcome to the Farm, 15 W Illinois St 
More Info: eventbrite.com  

Find Something Unique at the Cupid’s Vintage & Artisan Fest

Find the perfect gift—or treat yourself—at this sprawling marketplace packed with vintage treasures, handmade goods, and gourmet treats. With over 100 vendors rotating daily, no two shopping experiences are the same. From unique home décor to locally made accessories and art, this fest offers something for every style and taste.

Date: February 15-16 
Time: 11AM-5PM 
Cost: Free 
Location: Artifact Events, 4325 N Ravenswood Ave 
More Info: eventbrite.com

Rev Up for the Chicago Auto Show

Gear up for the nation’s largest and longest-running auto show, where the latest models and concept cars take center stage. Test drive vehicles, experience cutting-edge tech, and get a firsthand look at what’s next in the automotive world.

Date: February 15-16 
Time: 10AM-9PM 
Cost: $12+ 
Location: McCormick Place, 2301 S King Dr 
More Info: chicagoautoshow.com

Take Your Seat for Chicago Theatre Week

It’s the last weekend to snag discounted tickets to some of Chicago’s best performances during this citywide celebration of theater. From Broadway-caliber productions to intimate storefront shows, the lineup offers something for every taste. With over 100 productions to choose from, it’s the perfect excuse to experience the city’s performing arts scene—without breaking the bank.

Date: February 14-16 
Time: Various Times 
Cost: $15+ 
Location: Various Locations 
More Info: choosechicago.com

Shop Small at The Market Shop Pop-Up

Shop small and discover big finds at this pop-up market. Featuring local artisans, handmade goods, and delicious bites from market eateries, it’s a one-stop shop for unique gifts and treats. Whether you’re browsing for home décor, accessories, or just a snack, expect plenty of charm and creativity under one roof.

Date: February 15 
Time: 11AM-6PM 
Cost: Free 
Location: Time Out Market Chicago, 916 W Fulton Market 
More Info: eventbrite.com

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