Chicagoland Real Estate Happenings
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Chicagoland's Most Charming Winter Getaways for a Weekend Retreat
Our real estate agents love Chicago in the wintertime. It's the perfect place to capture the magic of the winter season, and there are limitless ways to enjoy winter in Chicagoland.
Weekend Getaways In and Around Chicago
If you're planning a snowy getaway this season, we have some ideas. From a charming staycation in the heart of Chicago to an adventurous retreat in the surrounding areas, these are some of the best places to spend a winter weekend in Chicagoland.
The Godfrey Hotel - Chicago, IL
Address: 127 W Huron St, Chicago, IL 60654
A boutique hotel in Chicago's River North neighborhood, the
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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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