When it comes to holiday cheer, no city sparkles quite like Chicago.
Stroll through downtown to see skaters gliding across picturesque ice skating rinks, sip mulled wine as you shop the charming Christkindlmarket, or grab tickets for a merry holiday show. As the city transforms into a winter wonderland, even the city trains light up for the season with twinkling lights and visits from Santa himself.
Chicago’s hotels join in the merriment, too. Think rooftop igloos under the stars, towering trees covered in ornaments, whimsical family-friendly events, cozy bars wrapped in garlands, and so much more.
Here are just a few of the Chicago hotels that are going all out for the holiday season this year with decorations, special packages, activities, and more.
Discover Chicago hotels for the holidays 2025
Rooftop igloos at LondonHouse Chicago
LondonHouse Chicago’s rooftop transforms into a North Pole paradise when Rudolph’s Rooftop Winter Igloos pops up for the holiday season. The cozy, private, heated igloos offer some of the best views of the city, plus a menu of seasonal cocktails and bites. Check out LondonHouse’s Spa Stay package and indulge in a post-holiday shopping massage at the in-hotel spa.
Explore more: Check out more winter rooftops and igloos in Chicago this season.
Breakfast with Santa at Hotel Zachary
At Hotel Zachary, located directly across from Wrigley Field, guests can walk right out the door and into the festive magic of Christkindlmarket Wrigleyville. This magical German-inspired market features vendor booths with handcrafted gifts and seasonal treats, plus activities like ice skating, wreath-making workshops, and more festive fun.
Throughout the holiday season, Hotel Zachary will host fun family-friendly pop-ups like teddy bear tea time, breakfast with Santa, and private heated igloos.
Santa Suite at the Swissôtel Chicago
When Santa zooms into Chicago aboard his enchanted sleigh, he spends the night at his special suite at Swissôtel Chicago. This year, his massive Presidential Suite will brim with fifteen Christmas trees inspired by Chicago’s Sister Cities, each reflecting the magic of holiday markets from around the world.
The unique Santa Suite overlooks the breathtaking skyline and icy Lake Michigan, creating a truly enchanting holiday experience. You can pop in to say hello to Santa on public event days or even spend the night in the most decked-out holiday hotel suite in the city.
The Grand Tree at the Palmer House
Chicago’s historic Palmer House, a Hilton Hotel was first established in 1871 and has welcomed illustrious guests like Mark Twain, Louis Armstrong, Liberace, and almost every U.S. president since Ulysses S. Grant.
During the holiday season, guests gather around the Grand Tree in the gilded lobby for cocktails and brownies, which were invented in the hotel’s kitchen for the World’s Columbian Exposition of 1893.
A cozy rooftop pop-up at Pendry Chicago
Inside the landmark Carbide & Carbon building, Pendry Chicago is transforming into a holiday destination this winter. On the hotel rooftop, get cozy inside a private winter lodge during Château Carbide’s Winter Garden pop-up. Each lodge is outfitted with a private fire pit and a menu of warm spiced cocktails.
The downtown hotel will also host live jazz on Saturdays, boozy holiday tea, and more magical holiday events throughout the season.
Winter fun near Sophy Chicago
Spend a winter weekend at the Sophy Hyde Park, a boutique hotel situated near the heart of the holiday action. Visit the Museum of Science and Industry, where the Christmas Around the World and Holidays of Light exhibit is always a holiday must-visit. Also in the neighborhood, the Midway Plaisance ice rink offers scenic views of the snow-dusted University of Chicago.
After a long day of holiday fun in the city, cozy up near the Sophy’s massive fireplace and order a seasonal cocktail to continue the festive mood.
Holiday tea at The Peninsula
The Peninsula Chicago hosts a lovely holiday afternoon tea throughout the winter season. Guests are seated around the grand, 20-foot Christmas tree for traditional English tea service that includes a variety of finger sandwiches, scones with homemade preserves and clotted cream, and petite seasonal pastries. The holiday season means a live string duo and visits from Santa on select dates.
Tip: Guests who book with the Merry & Bright Holiday Package can enjoy an in-room holiday tree or Menorah.
Christkindlmarket fun at The LaSalle
Book the Chicago Christkindlmarket Package and enjoy a stay in one of The LaSalle Chicago‘s luxurious room — and enjoy two souvenir mugs filled with hot wine at the iconic downtown Christmas market.
Enjoy wandering the charming German-style bazaar, while sipping the market’s signature mulled wine. Then, head to The LaSalle just a few blocks away for a cozy holiday escape thanks to in-room amenities like Lavazza espresso makers, 24-hour room service, and plush robes and slippers. Don’t miss the live jazz performances in the lobby lounge every Friday and Saturday evening.
Champagne toasts at The St. Regis Chicago
Kick off your holiday evening in Chicago with a pop of champagne! On select evenings in December, guests at The St. Regis Chicago gather to witness famous Chicago actors, journalists, and TV hosts slice open bottles of bubbly in dramatic fashion. It’s a sparkling salute to the season, steeped in tradition and fizzing with the holiday spirit.
The St. Regis Chicago will also be hosting a coat drive in partnership with local nonprofit Cradles to Crayons. Plus, book your holiday meal at buzzy in-house restaurants like Miru and Tre Dita.
In-room treats at the Four Seasons
Book the Festive Package at Four Seasons Hotel Chicagoand you can expect the in-room ice cream cart to roll on into your luxury suite. The cart features everything your family needs to build-your-own ice cream sundaes, including a variety of fun toppings and flavors with holiday flair.
Cap a day of holiday fun with festive cocktails at the Mile High Cocktail Club, an exclusive cocktail destination situated in the clouds high above the hustle and bustle of The Mag Mile on the 46th floor of the Four Seasons Chicago.
Don’t forget to take a dip in the iconic indoor pool that starred in Home Alone 2: Lost in New York. While the film famously features New York’s Plaza Hotel, the unforgettable pool scene was actually filmed right here at the Four Seasons Hotel Chicago!
