The Ultimate Winter Chicago Bucketlist

Wintertime is approaching, which means you’ve probably been busy planning and preparing for the cold weather and holiday season. Despite the snow and ice, it is a festive time of year, and there’s no better place to enjoy it than in the heart of Chicago. This year, there will be some differences in wintertime activities and events, since many businesses and organizations are practicing established social distancing guidelines. To keep you safe, as well as have an exciting trip to Chicago, we’ve compiled the ultimate winter Chicago bucket list for 2020 to help you decide which events and activities to do.

Watch Art on theMart

Art on theMart is back! This 25-story video installation is displayed on the side of the Merchandise Mart. You’ll be able to see a new 30-minute program featuring Joffrey Ballet’s The Nutcracker, as well as works from the Art Institute of Chicago’s “Monet and Chicago” exhibition. Each program begins at 7 and 7:30 pm every evening through December 30. Generally, people like to watch Art on theMart on the Chicago Riverwalk between Wells and Franklin Street. There is a 100-person capacity limit and face coverings are required.

Play a game of curling at Whiskey Business

If you are a fan of curling, this activity is perfect for you. Dress up warmly, and then participate in a friendly game of curling on Whiskey Business’s outdoor rooftop. You’ll be able to order from their selection of rooftop cocktails, including their Spiked Cider and Hot Toddy drinks. Make a reservation before visiting Whiskey Business to play a game of curling and enjoy the rooftop atmosphere. 

Ice skate at Maggie Daley Park’s Skating Ribbon

Throughout December, you’ll be able to ice skate at Maggie Daley Park’s famous Skating Ribbon. The Skating Ribbon is not only at an iconic location, with the city’s sweeping skyline in the background, but it also features a winding pathway of ice instead of a traditional round rink. The best part of the rink is that it is free, you only need to pay for skate rentals. However, this year, you’ll need to make a reservation to keep social distancing guidelines. This activity is perfect for the entire family, and the Skating Ribbon is even open on holidays. 

View Lincoln Park’s ZooLights

Lincoln Park’s ZooLights display 2.5 million lights, giving you a one-of-a-kind experience. This holiday atmosphere offers a family-oriented celebration in Chicago’s well known Lincoln Park. ZooLights start on November 21 and continue through January 3 in Lincoln Park Zoo. Make sure to buy your tickets in advance to be able to enjoy the spectacular light display.

Try deluxe hot cocoa from BomboBar

BomboBar, located in West Loop and River North, offers deluxe hot chocolates during the wintertime. BomboBar’s Hotter Chocolates are deliciously decorated and perfectly Instagrammable. Their flavors include Banana Split, Carmel Apple Cider, and Chocoholic. If you’d like to, you can also personalize your hot chocolate by building your own. Spike your hot chocolate with Stoli Vanilla Vodka, Fireball Rumchata, or add CBD. BomboBar also is known for its other sweets, including its housemade gelato and bombolinis—Italian holeless doughnuts. Make sure to dress warm, since the West Loop location only has a window with outdoor seating, and the River North location is a pop-up. 

Planning your winter trip

Whether you choose to visit Chicago now or in the future, you’ll have a unique and thrilling experience, not to mention the stunning landscapes you’ll be able to see. After you’ve selected your travel dates, you’ll need to decide where you’ll stay on your trip. Consider booking a hotel located in the heart of the city, close to nearly everything. Next up, pack your bags with essentials like warm clothes and a face covering to keep you safe and healthy. Now you’re ready for your upcoming trip to Chicago filled with breathtaking adventures and spectacular sights. 

Need a place to stay when visiting Chicago? Book your reservation here.