“City sidewalks, busy sidewalks, dressed in holiday style,” goes the old standard. And if the various December pop-ups that Chicago’s swankiest hotels have cooked up this year are any indication, it’s still just as relevant as ever.
Whether you’ve got in-laws to stash, a family tradition to keep, friends to meet or just need a place to crash the night of your office holiday party, we’ve compiled seven holiday-themed offerings around the city below.
Who says you can’t buy Christmas spirit?
Hot Chocolate and Live Carolers at Hotel Monaco
The art deco boutique just off Lower Wacker is the ideal place to warm up and get into some holiday spirits. Their typical Thursday and Friday “nightcap program” has a holiday update: instead of their traditional live jazz, holiday carolers will descend on the Living Room lobby. Pull up a couch next to the fireplace and grab a boozy hot chocolate from the hot chocolate cart.
And if you can swing it, on December 6, the hotel will celebrate St. Nicolas Day. Each guest is outfitted with a stocking to hang outside their door. In the morning, enjoy the spoils of a visit from St. Nick.
In-Room Christmas Tree at Swissôtel Chicago
Swissôtel is all in on Christmas. Guests can stay in an “elf-decorated” room complete with Christmas tree. We said ALL IN on Christmas, so obviously there’s more. For the sixth year, they are converting their 2,000-square-foot Presidential Suite into the Santa Suite. And this year’s après-ski Swiss chalet theme comes with 16 snow-covered Christmas trees and a chairlift. The programming for this event is extensive, so check their website for family friendly and adults-only offerings.
Milk and Cookies Hotline at The Intercontinental
Guests at the Michigan Avenue mainstay need only pick up the phone for warm chocolate chip cookies and milk to appear at their room. They also get a direct line to the man in red, and can ask Santa if they’re one the nice or naughty list. For the nonbelievers, head to the famed pool to catch a dive-in movie. Enjoy a Christmas classic like Elf, A Christmas Story or Home Alone from the perch of a peppermint candy pool float.
The Presidential Suite at Waldorf Astoria Chicago
Looking for a more silver bells (read: silver spoon) experience? Plan a couples weekend in the festive, extravagant Presidential Suit atop Waldorf Astoria Chicago’s 26th floor. Holiday decorations spill across two king bedrooms, a private kitchen and a fireplace-equipped living room, where four guests can devour a custom tasting menu curated by renowned Chef Michael Mina. Wrap up in your hotel robe, gaze out at the view of the twinkling city and sip on the welcome bottle of Dom Pérignon and rare wine pairings selected by Margeaux Brasserie’s lead sommelier. Then hit they hay to dream of sugarplums and ways to spend the $1,000 credit to the hotel’s spa.
Ice Skating at Hotel Zachary
For a slimmed-down neighborhood version of the downtown experience, Wrigley Field’s Hotel Zachary grants guests access to the ice rink and Christkindlmarket at Gallagher Way. The hotel’s Winterland Package includes two seasonal cocktails, skate rental and two sets of winter hats, scarves and gloves. You can also take a break from the ice to book a two-hour session at Camp Zachary, a glamping pop-up serving bubbling cauldrons of large-format cocktails. Imagine spending the afternoon outside Wrigley with a hot toddy in hand and a canvas tent above you, keeping the wind at bay.
Happy’s Bar at the Chicago Athletic Association
The annual holiday pop-up bar returns to the ground floor of the Chicago Athletic Association. Tinsel as far as the eye can see and eggnog shots and specials on Schlitz beer behind the pine. They’ve also got a DJ, bingo, karaoke, a gingerbread house competition and, hell, even a dog night. Merry Christmas ya filthy animal.
Curling at The Gwen
It’s ice-less curling, so there won’t be Olympic scouts milling around, but there will be cocktails, firepits and a wooden cabin to sample an Alpine-inspired rooftop menu. Curling is $25 per person for 30 minutes, and includes a cocktail. You don’t need to be a hotel guest to enjoy this amenity; book through Open Table below.
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