Sky Rink at the Peninsula
Pierre Sanders – LondonHouse
This isn’t just any ice rink! Nestled four floors above Michigan Avenue, Sky Rink not only offers stunning skyline views, but also a fun winter experience! After you’re finished gliding around the 2,100 square foot rink, have a delicious bite at Shanghai Terrace, the acclaimed Chinese restaurant on site.
Millennium Park Ice Skating
Henna Khemani – St. Jane Hotel
Just below The Bean, this iconic rink at Millennium Park is fun for the entire family. Skating is free and skates are available to rent and you can glide around til your hearts’ content. Bonus: on Friday, Saturday, and Sunday, the rink offers skating lessons!
City Winery Heated Domes
Kyle Franscis – Ritz-Carlton
The Riverwalk isn’t just for the summertime! Head to the Chicago Riverwalk to City Winery, where you can reserve a heated dome to enjoy your meal outdoors. Bask in your own little snow globe while sipping unique wines and perfectly paired dishes.
Polar Adventure Days at Northerly Island
Mark Kraemer – Hotel Palomar
Explore Chicago in a whole new way this winter with Polar Adventure Days. Come face-to-face with animals like Siberian Huskies, wolves, and birds of prey, make nature-inspired winter crafts, explore Northerly Island on snowshoes, and much more.
Navy Pier Winter WonderFest
Erica Abdnour – Concierge Preferred Magazine
For exciting, winter-themed family fun, head to Navy Pier’s Winter WonderFest. Everyone will love the opportunity to explore 170,000 square feet of fun attractions like slides, rides, climbing walls, indoor skating, and food stations. Make sure to take a few family selfies with the beautiful holiday and winter-themed decorations while you’re there!