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.
Have Fun at the Milk & Cookies Art Party
Drop the kids off for a night of creativity while you enjoy a well-deserved break. Young artists will craft Valentine’s-themed masterpieces under the guidance of expert instructors, all while enjoying pizza, milk, and cookies. A fun, hands-on way for kids to celebrate the holiday—and for parents to sneak in a date night.
Date: February 14
Time: 6PM-8PM
Cost: $25+
Location: Community Center, 1619 Wesley Ave, Berwyn
More Info: allevents.in
Try Everything at the 2025 Winter Beer Fest
Celebrate winter with craft beer at this annual festival, featuring breweries from Chicagoland and beyond. Guests can sample up to 20 different pours while enjoying bonfires, outdoor seating, and food truck fare.
Date: February 15
Time: 2PM-6PM
Cost: $50+
Location: Ty Warner Park, 700 Blackhawk Dr, Westmont
More Info: westmontparks.org
Brew Like a Pro at the Roasting & Barista Experience
Take your coffee obsession to the next level with this interactive deep dive into roasting and brewing. Learn to roast your own beans, perfect barista techniques, and explore the journey from farm to cup. Whether you’re an espresso aficionado or just love a good brew, this hands-on experience is sure to hit the spot.
Date: February 15
Time: 3PM-6PM
Cost: $45
Location: The Coffee Shop, 163 S Oak Park Ave, Oak Park
More Info: gatewaytothepatokas.com
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
