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Eight Things To Do in the City and Western Suburbs: Dec. 19–21, 2025
Winter weather has arrived! Layer up, follow the holiday lights, and catch a few can't-miss events this weekend.
Pair a festive feast with holiday lights at Dinner with Santa.
Brookfield Zoo Chicago blends dinner plans with holiday spectacle during this evening event that pairs a seasonal buffet with a visit from Santa himself. Families can sit down to a festive meal before heading out to explore the zoo's Holiday Magic displays, where illuminated paths and animal habitats set the scene for the night.
Date: Dec. 19–21
Time: Fri 5:30 p.m.; Sat & Sun 3:30 p.m. or 5:30 p.m.
Cost: $35+
Location:
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Five Things To Do in the Northern Suburbs: Dec. 19–21, 2025
Winter weather has arrived! Layer up, follow the holiday lights, and catch a few can't-miss events this weekend.
Dig through retro finds at Illinois Vintage Fest.
Illinois Vintage Fest takes over the Lake County Fairgrounds with a large-scale indoor market dedicated to vintage clothing, accessories, home goods, and collectibles. Vendors span multiple eras and styles, making it easy to browse everything from worn-in denim and band tees to retro décor and hard-to-find statement pieces. Dig through racks, discover unique finds, and spend the day browsing.
Date: Dec. 20–21
Time: 11 a.m.–6 p.m.
Cost: Free
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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:
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Local Chicagoland Charities to Support This Holiday Season
The holidays are the season of giving, and our real estate agents in Chicagoland are always glad for any opportunity to give something back to the city we love. Being good neighbors is one of the things that truly makes Chicago special.
Where to Donate or Volunteer in Chicagoland
We know we're not the only ones dedicated to helping our fellow Chicagoans in need this season. If you're wondering where you can donate or volunteer in Chicagoland during the holidays, we're here to point you in the right direction.
Christmas in the Wards - Chicago, IL
Address: 1030 E 87th St, Chicago, IL 60619
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Five Things To Do in the Northern Suburbs: Dec. 12–14, 2025
Winter weather has arrived! Layer up, follow the holiday lights, and catch a few can't-miss events this weekend.
Satisfy your sweet tooth at the Hot Cocoa Stroll.
Get dressed for an evening built around outdoor sets, live music, and plenty of themed stops. Visitors can rotate between Santa's open-air photo station, meet live reindeer, and loop around the pop-up skating rink before heading to the cocoa tents for a warm-up. Kids can have fun too, at craft tables and photo ops scattered throughout the plaza.
Date: Dec. 13
Time: 4–7 p.m.
Cost: Free
Location: Hawthorn...
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