The City of Chicago offers so many exciting experiences, especially during the wintertime. Here is a recommended list of the top five things not to miss during the Chicago holidays. Though this year’s season will be a bit different, many of these experiences are still open by reservation. Those that are closed are definitely worth checking out in the future.
1. Ice Skating at Millennium Park or Maggie Daley Park
I’ve saved the best for first—if you’re in Chicago for the festivities, you must go ice skating. At the foot of Michigan Avenue’s most beautiful buildings, The McCormick Tribute Ice Rink is a hallmark of Chicago winters. You won’t forget your time on the ice, surrounded by lit up trees and golden, glowing lamp posts. After you put away your skates, you can also venture up the stairs behind the rink to see the iconic Cloud Gate sculpture, or as it’s more commonly called, the bean. In the cold season, it is a sight dusted in white, reflecting the snowy city around it like a silver ornament.
You can also try your skills on the ice at the more recently opened, Maggie Daley Ice Skating Ribbon. Much bigger than your normal loop around the rink, the ribbon’s shape makes you feel like you are gliding along a winding river, passing by outdoor holiday décor with every turn. This rink is just a short walk past the bean, closer to the lake.
2. Macy’s Holiday Window Display
You can’t have a Chicago holiday without going to see the Macy’s windows. Every year on State Street, Macy’s decorates their window displays to tell a festive story. The storyline is different and the elaborate details and ornamentations more enticing with every new season. After a slow walk and gawk by the building, you can head inside the seven-story department store to do some holiday shopping. Each floor is decked out with garlands, colorful bulbs, and stars that dangle from the ceiling. If you get hungry, you can dine under a four-story Christmas tree in the Walnut Room—the first restaurant ever opened in a department store.
3. The Science and Industry Tree Exhibit
The Science and Industry Museum is one of the most exciting and unique museums I have ever been to. Their Christmas Around the World exhibit is no exception to this label. During the holidays, the museum puts out forty Christmas tree displays. These trees and their extravagant decorations represent different holiday cultures from all around the world. This experience is sure to put you in the celebratory spirit and is a great one to explore.
4. Dine Up Above the Lights
There’s nothing like a good birds-eye view of the city, especially when it is covered in powder and holiday lights. For the best sights, you must visit the John Hancock Signature Room and the London House Rooftop. The Signature room restaurant sits on the 95th floor of the John Hancock Building. With 360-degree windows, it overlooks the entire city and some suburbs. It is a great place to look out over Lake Michigan and its surrounding rooftops while you enjoy some good food. Check the dress code on the website before you go. For the same overlooks, and a less formal setting with lower prices, you can also visit the Signature Lounge on the 96th floor. Believe it or not, the best view is from the women’s bathroom. Customers under 21 are not allowed into the Lounge without a parent.
Another up-high dining experience with great food and holiday décor can be found at the London House Rooftop. While this building is certainly shorter, it offers different sights of the Chicago River and some of the most historical and famous buildings the city has to offer. Once you’re done eating in this area, you can walk along the Chicago Riverwalk or explore the shops on the Magnificent Mile.
This German-style market has been a long-standing tradition in Chicago. Vendors come from near and far to serve up delicious food and sell unique clothes, decorations, toys, and games. These wood-trimmed booths are fun to explore, and the hot chocolate is especially amazing. I would recommend going early if you want to visit, as the crowds and lines grow throughout the day.