After Thanksgiving, Chicago’s most festive hot spots take you above the lights—or at least strolling through them.

By Jess Hoffert
Godfrey Hotel

Chicago has a way of constantly one-upping itself. If you’ve snapped an after-dark selfie at The Bean in summer, you can imagine the allure in winter, when you can glide past the silvery orb on Millennium Park’s free skating rink, snowflakes and holiday lights mirrored in the reflection. But why stop there? Ride an elevator to zip across a rooftop rink against the glittering skyline backdrop. Or try your hand at curling atop a chic hotel. Then sip cocktails in the confines of see-through heated globes—tailor-made for Santa spotting.

The Gwen Hotel Curling Court.
Courtesy of The Gwen

And that’s just the rooftops. Don’t ignore the ground game. Walk through light displays with bulb numbers soaring into the millions. Pose by a four-story tree. Shop at one of the biggest German markets this side of Nuremberg. Yes, we’re being a little hyperbolic. But it’s Chicago at Christmas: The sky’s the limit.

Up on the Rooftop

The Peninsula Sky Rink Twinkling pine trees and towering skyscrapers surround the skating rink on The Terrace at The Peninsula Chicago hotel. You don’t have to be a guest to grab skates from the Sky Rink Chalet, which also serves hot chocolate, cider and snacks. No matter the temp, you’ll feel warm knowing your donation for skating goes to children’s charities in the area.

The Peninsula Chicago.
Starboard And Port

Upstairs at The Gwen If you’re like us and watch the Winter Olympic Games thinking, “Gee, curling looks … interesting,” you can give it a whirl (without the ice or the brooms) on the roof of The Gwen Hotel. There’s no manic sweeping—just “throwing” (sliding) the stones across a slick surface and aiming for the “button” (bullseye). Afterward, hang at the communal table with built-in firepits and share the gold medal-worthy mulled wine (it serves four to six people).

The Gwen Hotel.
Neil Burger

Winter Wonderland at The Godfrey Violet lights and transparent geodesic domes lend an otherworldly vibe to the sprawling roof of The Godfrey Hotel Chicago. Book one of the heated “igloos” for a VIP lineup of all things cozy: s’mores kits, hot toddies and comfort-food small plates such as Lamb Lollichops with orange-caramelized potatoes. The only downside: After your self-induced food and drink coma, you can’t cuddle up in these cozy domes overnight.

The Godfrey.
Starboard and Port

Soaring Stats

1 million people visit Chicago’s annual Christkindlmarket in Daley Plaza (November 15–December 24, 2019). Plus, more than 60 percent of the vendors come from Germany, many bringing traditional sweets, steins and goods.

Christkindlmarket.
Eric James Walsh

52 crab apple trees will form a canopy of lights at the first Lightscape at the Chicago Botanic Garden. Direct from London, the production creates a glowing trail of “singing trees,” electric vines and other storybook touches (November 22, 2019–January 5, 2020).

37 degrees is the average high temp in Chicago during December. Not too bad … but don’t underestimate that lakefront windchill.

30,000 lights encircle the 45-foot-tall Grand Tree at the Museum of Science and Industry. The tree is flanked by more than 50 smaller trees and displays, each themed to a different holiday culture and custom (November 14, 2019–January 5, 2020).

Museum of Science and Industry.
Courtesy Of Museum of Science And Industry

170k square feet of indoor fun awaits at Fifth Third Bank Winter WonderFest on Navy Pier (December 6, 2019–January 12, 2020). Family-centric attractions include giant slides, the Kringle Carousel and the Xfinity Ice Skating rink.

Navy Pier.
Courtesy Of Navy Pier

1,341 performances of the musical Hamilton will have taken place in Chicago when it closes on January 5, 2020. And some 2.6 million people will have seen the show during its epic run.

Night Lights

BMO Harris Bank Magnificent Mile Lights Festival

Chicago looks skyward to kick off its holiday. Spot multistory helium balloons, showers of confetti and fireworks over the Chicago River on the Saturday before Thanksgiving. Through December, more than a million lights adorn buildings and trees along Michigan Avenue. Take them in while shopping the Mag Mile’s hundreds of stores or gazing down from hotel windows.

Illumination: Tree Lights at The Morton Arboretum

Enchanted forests are usually reserved for fairy-tale plot twists. But things get real here as trees respond to hugs and sing with light effects along a meandering 1-mile path in suburban Lisle. Adding to the magic: illuminated Alexa and Joe, two of the arboretum’s popular troll sculptures.

ZooLights at Lincoln Park Zoo

If there was a competition for best zoo lights, this one would dominate, paws down. More than 2.5 million lights illuminate megawatt displays, many shaped like animals. Snag 3-D holiday goggles for extra eye-popping action.

Lincoln Park Zoo.
Courtesy of Lincoln Park Zoo

Santa’s Eye View

Make like a reindeer and join Santa in the clouds.

No magical sleigh? For just shy of $700, Chicago Helicopter Experience can give you and three friends the ultimate light show from the air: glass-encased skyscrapers lit like boxy Christmas trees, a ribbon of twinkling lights along the Magnificent Mile and the colorful menagerie above ZooLights at Lincoln Park Zoo. Pilots narrate the 15-minute journey so you don’t miss a thing.

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