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Five Things To Do in Chicago: Dec. 19–21, 2025
Winter weather has arrived! Layer up, follow the holiday lights, and catch a few can't-miss events this weekend.
Enjoy two nights of action at Modo Casino PBR Chicago.
Professional Bull Riders return to the United Center for two nights of high-stakes competition as the Unleash the Beast tour makes one of its few Chicago stops. The event brings the sport's top riders face-to-face with elite bulls in a rapid-fire series of eight-second matchups, where every ride counts toward World Finals qualification. It's a rare chance to see the tour in Chicago—and one of the season's earliest tests for riders chasing a title run.
Date: Dec. 19–20
Time: Fri 7:45 p.m.; Sat 6:45 p.m.
Cost: $32+
Location: United Center, 1901 W. Madison St.
More Info: unitedcenter.com
Bring the family to the Millennium Park Holiday Sing-Along.
Set against the city's most recognizable backdrop, Millennium Park's Holiday Sing-Along turns Cloud Gate into an open-air concert space, inviting the public to sing along with rotating choral ensembles. Each set highlights different vocal groups, with songbooks available on-site and ASL interpretation provided.
Date: Dec. 19
Time: 6–7 p.m.
Cost: Free
Location: Millennium Park
More Info: chicago.gov
Make keepsakes at Impression Ornaments with Aubrey Ingmar and Zora.
This hands-on workshop at the Learning Lab invites participants to experiment with air-dry clay, creating sculptural ornaments using impressions from everyday found objects. Led by artist Aubrey Ingmar in connection with the Not a Soft Thing exhibition, this session focuses on process and tactile exploration.
Date: Dec. 20
Time: 12–2 p.m.
Cost: Free
Location: Chicago Cultural Center, 78 E. Washington St.
More Info: chicago.gov
Shop local at the Chicago Holiday Market.
The Experimental Station hosts this seasonal market, spotlighting local artisans across jewelry, home goods, clothing, and visual art, alongside food vendors and family-friendly programming. Beyond shopping are live demonstrations and workshops woven into the day's schedule.
Date: Dec. 20–21
Time: 10 a.m.–5 p.m.
Cost: Free
Location: Experimental Station, 6100 S. Blackstone Ave.
More Info: eventbrite.com
Browse the Renegade Craft.
Renegade Craft's winter fair returns to the West Loop with more than 170 curated artists showcasing handmade goods, art, fashion, home décor, and more. Known for its careful vendor selection, the market balances variety with quality, making it a one-stop shop for shoppers looking beyond mass-produced gifts.
Date: Dec. 19–21
Time: Fri 5–8 p.m.; Sat & Sun 11 a.m.–5 p.m.
Cost: $5 Suggested Donation
Location: Morgan Manufacturing, 401 N. Morgan
More Info: renegadecraft.com
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