Holiday Getaway to Chicago

Chicago has a way of constantly one-upping itself. If you've explored the many attractions of Millennium Park in summer, you can imagine the allure in winter, when you can glide on the park's free skating rink, perhaps surrounded by twirling snowflakes. 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.

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.

Skate on a Rooftop

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.

Give Curling a Whirl

If you're like us and watch winter sports thinking, "Gee, curling looks … interesting," you can give it a whirl at The Upstairs at The Gwen terrace 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 fire-pit table, share a gold medal-worthy hand-crafted cocktail, and make some s'mores.

Stone's Throw Curling is also expected to return at The Emily Hotel by January.

Be at Home in a Dome

Violet lights and transparent geodesic domes lend an otherworldly vibe to the sprawling roof of The Godfrey Hotel Chicago, one of several rooftop bars and igloos in Chicago. Sip champagne and nosh on shareable sushi boards, wagyu sliders and charcuterie when you book one of the heated "igloos" available in different sizes with the purchase of bottle service. The only downside: After your self-induced food and drink coma, you can't cuddle up in these cozy domes overnight.

More Holiday Events in Chicago

One million people visit Chicago's annual Christkindlmarket in Daley Plaza (November 17–December 24, 2023). Plus, more than 60 percent of the vendors come from Germany, many bringing traditional sweets, steins and goods.

The Wintrust Magnificent Mile Lights Festival enters Chicago's holiday lights season with a spectacular display. 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.

This year marks the 5th annual celebration of lights at Lightscape at the Chicago Botanic Garden (November 10, 2023–January 7, 2024). See first-time installations as well as old favorites.

About 30,000 lights encircle the 45-foot-tall Grand Tree at the Museum of Science and Industry's annual Christmas Around the World and Holiday of Lights. The tree is flanked by more than 60 smaller trees and displays, decorated by volunteers to represent holiday traditions from cultures around the globe (November 18, 2023 to January 5, 2024).

Illumination: Tree Lights at The Morton Arboretum (November 18, 2023 through January 6, 2024) brings magic to this space in suburban Lisle. 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. Every year brings new displays as well as returning favorites.

ZooLights Presented by ComEd and Invesco QQQ at Lincoln Park Zoo (November 17, 2023-January 7, 2024) is a community favorite. 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.