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.
Make a Splash at Polar Plunge Chicago
Ready to take an icy dip for a great cause? The annual Polar Plunge returns to North Avenue Beach, inviting brave participants to run into the freezing waters of Lake Michigan in support of Special Olympics Chicago. Whether you’re plunging solo or with a team, expect a lively atmosphere with creative costumes, spirited spectators, and plenty of post-plunge celebrations. Not ready to dive in? You can still donate or cheer on the participants from the sidelines.
Date: March 2
Time: 8AM
Cost: Raise $200 Minimum to Participate
Location: North Avenue Beach, 1601 N Lake Shore Dr
More Info: specialchildrenscharities.org
Find Your Center at Sag Hej Day
A full day dedicated to wellness, creativity, and community, this Scandinavian-inspired event transforms Bramble Arts Loft into a hub for self-care. Start the morning with yoga and sound baths, or dive into interactive workshops on interior design for mindfulness, financial planning, and sexual wellness. Throughout the day, enjoy tarot readings, complimentary massages, art activities, and empowering performances from the Youth Empowerment Performance Project.
Date: March 2
Time: 10AM-3PM
Cost: Free With RSVP
Location: Bramble Arts Loft, 545 N Clark
More Info: app.glueup.com
Go on a Winter Wine Walk
Stroll through more than a dozen local shops while sampling over 20 wines, from bold reds to crisp whites. Many participating businesses will offer exclusive shopping discounts and small bites to pair with your tastings. Each ticket includes a commemorative tasting glass and an event guide to help you navigate the neighborhood’s best sips and shops.
Date: February 28
Time: 5:30PM-8:30PM
Cost: $40+
Location: W Roscoe St from N Damen Ave to N Western Ave
More Info: lakeviewroscoevillage.org
Feel the Rhythm at the Chicago Winter Jazz Fair
The Chicago Winter Jazz Fair brings together an exciting lineup of performances, artist discussions, and vendor booths celebrating the city’s rich jazz scene. Whether you’re into traditional swing, avant-garde improvisation, or contemporary fusion, there’s something for every kind of listener. Stop by to hear acclaimed musicians, explore new sounds, and dive deep into Chicago’s jazz legacy.
Date: February 28
Time: 12PM-7:30PM
Cost: Free
Location: Jazz Institute of Chicago, 410 S Michigan Ave
More Info: jazzinchicago.org
Join the Puzzle-Hero Competition: A C2E2 Pop-Up Party
Calling all puzzle pros! Revolution Brewing and C2E2 team up for a high-energy jigsaw puzzle showdown. Teams will race to complete a mystery 500-piece puzzle, with the fastest solvers winning a prize package featuring C2E2 tickets, exclusive Revolution Brewing swag, and more. Enjoy a brew while you strategize, and embrace your inner “dissectologist” for a night of friendly competition.
Date: February 28
Time: 6PM-8PM
Cost: $8+
Location: Revolution Brewing, 3340 N Kedzie Ave
More Info: revbrew.com
