There’s something magical about Chicago during the holiday season. In December, the Windy City transforms into a winter wonderland, with lights reflecting off Lake Michigan, holiday markets to explore, and world-class performances to enjoy. If you’re planning a stay in Chicago this winter, we’ve got the scoop on the best seasonal experiences in town—all conveniently close to Arlo Chicago, the ideal homebase for all your holiday adventures.
Hit The Ice at Millennium Park
A 5-minute walk from Arlo Chicago
Yes, it’s cold out, but when you lace up your skates and glide onto the ice, you’ll discover the magical side of this chilly time of year. Chicago has several skating venues, but our favorite is the iconic McCormick Tribune Ice Rink in Millennium Park, a short walk away from the hotel. You can rent a pair of skates or bring your own to savor the experience of skating against a backdrop of the Chicago skyline. The rink is free and open throughout the winter season.
Skate Through A Park
A 12-minute walk from Arlo Chicago
Instead of the typical ice-skating rink setup, the Maggie Daley Ice Skating Ribbon allows you to skate along a quarter-mile ribbon that winds through the park. Follow the curving path and take in the scenic surroundings that make it feel like you’re in a winter fairytale. Tickets are $5 if you bring your own skates, or $17 with skate rentals.
A Cirque Christmas Classic
A 5-minute walk from Arlo Chicago
Stroll over to the Chicago Theatre between Dec. 11–28 to take in Cirque du Soleil’s production of ’Twas The Night Before. This infamous acrobatic troupe put an energy-filled, theatrical spin on the classic Christmas tale, in a high-octane show perfect for all ages.
The Nutcracker
A 4-minute walk from Arlo Chicago
Ballet enthusiasts won’t want to miss The Joffrey Ballet’s staging of The Nutcracker. The company’s critically acclaimed interpretation of the holiday classic features Christopher Wheeldon’s innovative choreography set against the backdrop of the 1893 Chicago World’s Fair. It’s a Chicago twist on a timeless story, complete with Tchaikovsky’s iconic score performed by a live orchestra. Performances run from Dec. 5–28.
Hot Tub Cruise
A 10-minute walk from Arlo Chicago
Looking for something completely different? Try a hot tub cruise on the Chicago River. Yes, that’s right—you can soak in a heated hot tub while floating past Chicago’s architectural landmarks. This might just be the most original way to experience the city’s famous skyline—staying toasty warm despite the winter chill along the way. The hot tub boats can fit up to six passengers, and it’s BYO drinks (no glass), as well as swimsuits, towels, flip-flops and earmuffs!
Shop A Holiday Market
A 7-minute walk from Arlo Chicago
The Christkindlmarket brings a taste of Germany to downtown Chicago during the festive season. This authentic German holiday market features wooden huts where vendors showcase traditional crafts, ornaments, food, and glühwein (mulled wine). Soak up the scent of roasted almonds and bratwurst as you browse for gifts and don’t leave without trying a fresh pretzel or some lebkuchen (German gingerbread cookies).
Play & Browse A Pop-Up
An 8-minute drive from Arlo Chicago
The Jack Frost Fulton Market Pop-Up provides a super-fun, Instagram-worthy winter experience perfect for group hangs. The seasonal venue offers themed cocktails, cozy winter vibes, and a festive atmosphere. Try your hand at curling or axe-throwing, and battle it out in the winter bumper cars. Tickets start at $30.72 per adult and $28.30 for kids aged 5–11. Add-ons and bundles including beverages are also available.
Rides & Games At Navy Pier
A 5-minute drive from Arlo Chicago
For family-friendly entertainment, Winter WonderFest at Navy Pier offers theme-park-like attractions perfect for kids and thrillseekers. Brave rides like the Cliffhanger and Zero Gravity, or opt for the tamer kiddie train, the bumper cars, or on the ice rink. Tickets start at $25 per person, and each ticket includes a ride on the Centennial Wheel, which will whisk you to a height of nearly 200 feet, where you can take in epic views of the Pier’s holiday lights. Winter WonderFest is open daily through Jan. 4.
Visit The Animals
A 10-minute drive from Arlo Chicago
Animal lovers will get a kick out of ZooLights at Lincoln Park Zoo. This seasonal highlight transforms the zoo into an illuminated wonderland with millions of twinkling lights, animated displays, and holiday music. You can visit the animals in their winter habitats while enjoying ice carving demonstrations, warming up with hot chocolate, and taking in the magical light displays throughout the grounds. Tickets are $7, or free with advance registration on select Mondays. ZooLights runs from 4:30pm–9pm through Jan. 4, 2026.
However you spend the holidays in Chicago this year, remember that you always have a warm and cozy place to stay or to pop into for a festive beverage or holiday meal. Come see the team at Arlo Chicago, and ask us about even more fun and festive things to do this season. Happy Holidays!
