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
