There’s no better place to experience the magic of the holidays than Chicago. The city is full of exciting events that offer everything from warm beverages to dazzling light displays and cozy, festive vibes. Check out these 10 holiday events that promise to make your season merry and bright.

Christkindlmarket (Until Dec 24, 2024)

Held at Daley Plaza, this iconic German holiday market offers a blend of European traditions and Chicago’s winter charm. Browse handcrafted goods, indulge in delicious German foods, and warm up with a cup of spiced glühwein served in collectible boot mugs​. Enjoy the festivities with a hot drink in hand, or opt for a cozy beer from the local stands.

Source: Christkindlmarket 

Winterland at Gallagher Way (Dec 6 – Dec 22, 2024)

Adjacent to Wrigley Field, this seasonal village transforms into a winter wonderland with ice skating, carnival rides, and holiday movie nights​. There’s also a festive market where you can sip hot chocolate or grab a mulled wine while shopping for unique gifts. Don't miss the chance to get a photo with Santa!

Source: TimeOut

Light Up the Lake at Navy Pier (Dec 5, 2024 – Jan 5, 2025)

This annual event lights up the lakefront with an incredible outdoor display of lights, complemented by a variety of activities like ice skating, holiday drone shows, and an artisan market​. You can enjoy cozy fire pits with a warm drink, or sip seasonal cocktails while watching the festive fireworks on Saturdays.

Source: YourChicagoGuide

Clark Street Cookie Crawl (Dec 8, 2024)

Sweeten up your holiday with a cookie crawl through Lincoln Park. This event lets you sample delicious holiday cookies, hot chocolate, and festive treats at local spots like Molly’s Cupcakes and XO Marshmallow​. Want a boozy twist? Opt for the Boozy Admission to add some holiday spirits to your treats!

Source: TimeOut

Sauced Night Market Before Xmas (Dec 13 – Dec 14, 2024)

Head to the Chicago Athletic Association for a special holiday edition of the Sauced Night Market​. Sip craft cocktails while shopping for handmade goods and artwork, or grab a bite from local food vendors offering delicious festive dishes.

Source: Facebook

Illumination: Tree Lights at Morton Arboretum (Until Jan 4, 2025)

Experience a dazzling light show amid the trees at Morton Arboretum, a mile-long walk featuring synchronized lights and music​. For an extra festive touch, “IllumiBrew” offers a chance to sample local beers and ciders in a holiday atmosphere.

Source: Chicago Mag

Holiday Magic at Brookfield Zoo (Until Dec 31, 2024)

Visit the Brookfield Zoo, where over two million lights illuminate animal sculptures and trees​. Warm up with a cup of spiced wine or hot cocoa as you explore the zoo’s magical light displays and a festive market.

Source: Brookfield Zoo

Andrew Bird’s Gezelligheid Holiday Concert Series (Until Dec 13, 2024)

Enjoy an intimate holiday concert by Andrew Bird, where the atmosphere is cozy and festive​. The concerts are an eclectic mix of seasonal tunes, offering a perfect setting for a glass of wine or holiday-inspired cocktails.

Source: Secret Chicago

Candlelight Christmas Concerts (Dec 11 & Dec 20, 2024)

For a serene experience, attend a candlelit classical concert featuring holiday carols at venues like Stan Mansion and St. Luke’s Episcopal Church​. These concerts are the perfect opportunity to enjoy a glass of wine or champagne in an enchanting atmosphere.

Source: Secret Chicago

Mariah Carey’s Black Irish Holiday Bar (Until Dec 29, 2024)

For a pop culture twist on the holidays, visit the Mariah Carey-themed pop-up bar at Virgin Hotels​. Enjoy signature cocktails made with Black Irish liqueur, and maybe even get a photo with a festive Mariah-themed backdrop!

Source: TimeOut

Chicago knows how to celebrate the holidays with style and flair. Whether you’re enchanted by sparkling lights, indulging in festive treats, or seeking unique entertainment, these events promise unforgettable memories. Bundle up, bring your holiday cheer, and immerse yourself in the festive spirit of the Windy City!