Macy's Great Tree
Photograph: Jaclyn Rivas for Time Out
Photograph: Jaclyn Rivas for Time Out

The best Christmas things to do during the holidays in Chicago

Experience the holidays in Chicago with beautiful lights, festive theater productions and bustling markets.

Emma KruppJeffy Mai
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Chicago winters can be a bit of a drag, to say the least, but the holidays offer a shimmering diversion from long nights and frosty weather. This season, you'll find plenty of festive events and celebrations to put you in a holiday mood as temperatures start to drop, from glittering Christmas lights in Chicago and Christkindlmarket in Daley Plaza to sing-alongs at the Music Box and Millennium Park. You can even take a spin around the City of Chicago Christmas tree at ice skating rinks downtown and warm up afterwards with a hot cocktail at holiday pop-up bars scattered throughout the city, or plan a festive night of theater thanks to annual Christmas shows and concerts like The Nutcracker and A Christmas Carol. Whatever holiday you celebrate this time of year, you'll find plenty of ways to feel festive with our list of the best things to do during the holidays in Chicago. 

RECOMMENDED: Our complete guide to Christmas in Chicago

Best Christmas events in Chicago

  • Things to do
  • Ice skating
  • Millennium Park

Skate under the Chicago skyline and within eyeshot of the Chicago Christmas Tree at the McCormick Tribune Ice Rink in Millennium Park. Plus, take advantage of free skating lessons on most Saturdays and Sundays, where you can learn both beginner- and intermediate-level skills. Note that you'll need to make a free online reservation for both regular skating and lessons, and if it seems too warm to skate, call ahead—this rink is open through February 2, weather permitting.

  • Things to do
  • Ice skating
  • Millennium Park

Situated in the heart of downtown Chicago with the city's sweeping skyline as a backdrop, the Skating Ribbon at Maggie Daley Park is a winter attraction unlike any other. Skaters can lace up and wind around a winding ice-covered path that's twice the length of a lap around a traditional rink. Reservations for the popular ice rink should be made in advance, as they tend to fill up quickly.

Admission to the Skating Ribbon is free Monday through Thursday and for 11am sessions Friday through Sunday (and $5 for other time slots Friday through Sunday, as well as holidays) if you bring your own skates. No skates? Entry is $17–$23 if you need to rent a pair. The Ribbon stays open through March (weather permitting) and even offers hours on Thanksgiving Day, Christmas Eve, Christmas Day, New Year's Eve and New Year's Day.

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  • Things to do
  • Streeterville

Located on the terrace of The Peninsula Chicago, the 2,100-square-foot Sky Rink offers ice skating in the shadows of the city's tallest buildings, all while overlooking Michigan Avenue. Show off your skills in a winter wonderland featuring snowflake lighting and festive music, and when you need to warm up, grab a hot drink and snack at the Chalet.

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  • Nightlife
  • Pop-ups and food events
  • Loop

Immerse yourself in a picture-perfect whimsical décor, sparkling lights and breathtaking Chicago skyline views from the 22nd floor and indulge in a delightful selection of holiday-themed cocktails, including steaming spiced mulled wine and chilled festive drinks. LondonHouse Chicago's rooftop also offers cozy heated igloos, which can be booked by contacting rsvp@londonhouse.com; reservations require a $600 food and drink minimum.

  • Things to do
  • Near North Side

There’s plenty of cold weather fun to be had on the Art Deco-inspired terrace at the Gwen Hotel, which offers curling lanes plus fire pits and hot cocktails so you can warm up between rounds. Heat lamps are set up around the perimeter to keep things toasty and you can also hang out with a group around one of the fire tables.

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  • Things to do
  • River North

The Godfrey’s rooftop becomes a winter wonderland when the temperatures plunge, featuring clear heated igloos decorated with festive lights that can be booked for groups of up to 10 people indulging in bottle service. Even if you’re not going all out, you can hang out at a booth under the retractable roof or gather around an outdoor fire pit for s’mores and a hot cocktail.

  • Things to do
  • Loop

Look out over Lake Michigan and Millennium Park from the glass atrium on top of the Chicago Athletic Association hotel. The outdoor terrace is accessible year round and features fire pits to keep you toasty while you sip drinks. Cindy’s is running an après ski-inspired pop-up, with classic cold weather cocktails and themed decorations that transport guests to a snowy mountain getaway, daily through February 28.

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  • Nightlife
  • Pop-ups and food events
  • Loop

Fairmont Chicago has brought back its seasonal experience, Fairmont Lodge, for another year of wintry fun. The hotel’s lobby is transformed into a wonderland featuring themed décor, festive programming and seasonal menus. Guests can reserve a Lodge experience and indulge in hand-crafted cocktails and sweet and savory fondue, capped off with some tabletop s'mores. There’s also live entertainment Thursday through Saturday.

  • Things to do
  • Wrigleyville

Just because baseball season is over doesn't mean the action in Wrigleyville goes into hibernation. Alma, the Hotel Zachary bar located across from Wrigley Field, is bringing back its heated terrace globes from November 16 to January 26. Up to six guests can enjoy holiday cocktails or kid-friendly options like hot chocolate, eggnog or sparkling cider, plus a build-your-own s’mores station curated by Amy’s Candy Bar. The globes also come equipped with a record player so you can play some holiday tunes, as well as board games and Polaroid cameras to help capture those picture-perfect moments.

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