The Best Things To Do This Winter in Chicago—From Crusing in a Hot Tub on the River to Sipping Glühwein at the Best Christmas Market in the Country

Prepare to pull your down coat out from the depths of your closet, because this winter is expected to be one of the coldest since the Polar Vortex hit over a decade ago. However, we don’t let the freezing temperatures stop us from enjoying the city—in fact, we might even embrace the chill . After all, what’s the point of sipping mulled “Glühwein” if it’s warm outside? Here are the best things to do in Chicago this winter. Head to a holiday show this winter ---------------------------------------------------------------------------------------------- This winter in Chicago, head to Andrew Bird’s intimate Gezelligheid performances or the Joffrey Ballet’s reimagined Nutcracker —maybe even both? There are a lineup of festive shows to check out. 📍 Location: Chicago (various venues including Fourth Presbyterian Church, Lyric Opera House, Auditorium Theatre, and more) 🗓️ Dates: December 2–30, 2025 (with select events also on December 5–28, 2024 and December 20, 2025) Go ice skating at the Maggie Daley Ice Ribbon --------------------------------------------- There’s no better way to glide into winter than with ice skating in Chicago! One of our favorites is Maggie Daley Ice, the winding ribbon of ice curves up and down and features a 40-foot climbing wall with the city’s stunning skyline in the backdrop ! Canadian Pacific holiday train in Chicagoland ----------------------------------------------------------------------------------------------------------------------- Hop aboard the festive fun as the [CPKC Canadian Pacific holiday train](https://secretchicago.com/canadian-pacific-holiday-train-chicago-2025/) rolls through the Chicago suburbs with thousands of lights and free live concerts. Families can catch the illuminated train, enjoy outdoor performances, and revel in small-town holiday charm. 📍 Location: Franklin Park, IL (South side of Ruby Street Railway Crossing, north of Franklin Avenue) and Gurnee, IL (4460 Old Grand Avenue) 🗓️ Dates: Sunday, November 23, 5:30–6 p.m. and Tuesday, December 9, 5:15–5:40 p.m. Immersive Harry Potter Forbidden Forest trail near Chicago ------------------------------------------------------------------------------------------------------------------------------------------ Step into a moonlit world of spells, Patronuses, and magical creatures on the Harry Potter: Forbidden Forest Experience in Illinois, a nighttime trail inspired by the Harry Potter and Fantastic Beasts films. About an hour from Chicago, this limited-time walk lets fans cast charms, encounter Nifflers, Centaurs, and Hippogriffs, and sip Butterbeer under the stars. Tickets are available for select dates through early January 2026 , with weekday discounts during the Dark Arts season. Christkindlmarket returns to Chicago for the holidays ---------------------------------------------------------------------------------------------------------------------------------- The beloved German-inspired market returns to Daley Plaza, Gallagher Way at Wrigley Field, and RiverEdge Park in Aurora, offering a cozy atmosphere filled with European treats like bratwurst, pretzels, and mulled wine. Browse handcrafted gifts , enjoy live entertainment, and soak up the holiday spirit at all three sites, making it an essential winter activity in Chicago. 📍 Location: Daley Plaza (50 W. Washington St., Chicago), Gallagher Way at Wrigley Field (3635 N. Clark St., Chicago), and RiverEdge Park (360 N. Broadway, Aurora) 🗓️ Dates: November 21–December 24 (Daley Plaza & Aurora), November 23–December 31 (Wrigleyville) Hot tub boat cruises on the Chicago River -------------------------------------------------------------------------------------------------- Warm up this winter on the water with the Chicago Boat Company’s hot tub boats, a cozy way to cruise the downtown river. Each floating hot tub fits about five people and comes equipped with the essentials— cup holders, a phone mount, and a Bluetooth speaker; guests can even bring their own drinks. 📍 Location: Chicago River, departing with Chicago Boat Company (downtown Chicago) 🗓️ Dates: Select dates from November through March, Wednesday through Sunday Sip cocktails while curling up on a rooftop ------------------------------------------- Why limit rooftop season to just the summer? Visit Upstairs at The Gwen Hotel for a unique cold-weather retreat. The winter rooftop has curling, boozy hot chocolate, spiced mulled wine , and handcrafted signature cocktails this winter in Chicago. Your $25/person admission includes access to the curling court and firepit table for one hour, along with a featured seasonal treat—you can even add on gruyere fondue and lux s’mores fondue. Have the ultimate self-care day ------------------------------- This winter, don’t let your skin crack and dry out—give yourself a day that will leave you feeling radiant. We highly recommend SpaDerma, which offers a curated menu of treatments, including cutting-edge facial lasers, laser hair removal, and more. The best part is they’re currently hosting a holiday promotion. You can choose any three skincare services for 25% off, or four of the same treatment for 30% off, including Hydrafacial, DiamondGlow, chemical peels, Moxi, Halo, and more. Source: https://secretchicago.com/best-things-to-do-this-winter-chicago-2026/