Although Chicago is known for its amazing summers, there is still so much to do once the weather turns cold! Because it gets dark so early, it’s easy to see the city all lit up and get in the holiday spirit. So grab your mittens, bundle up, and read on for the best things to eat, see, and do in Chicago in the winter!
⇉ Chicago Summer Activities: The 21 Best Things to Eat, See, and Do
Disclosure: Some of the links below are affiliate links. When you purchase through links on my site, I may make a small commission (at no extra cost to you!).
Things to do in Chicago in winter
Go ice skating
Maggie Daley Park is home to the longest Ice Skating Ribbon in the USA (in the summer, it transforms into a rollerblading ribbon!). Admission is free, but it does cost money if you want to rent ice skates. With beautiful views of the skyline, this is a great place to go once it’s dark to see some twinkling city lights.
Drink mulled wine at Christkindlmarket
Christkindlmarket is an annual Christmas market that features local shops and restaurants housed in outdoor stalls. You can buy handmade nutcrackers, tree ornaments, and other decor, as well as freshly made Glühwein or roasted chestnuts. There’s nothing better than wandering around and soaking up the holiday merriment with a hot cup of spiced wine!
Go out for brunch
Honestly, this is something I recommend doing no matter what season it is. Chicago has a plethora of brunch places, many with bottomless mimosa or Bloody Mary deals. This is a great pregame activity for any of the other activities on this list as well! Pictured below is the donut wall and dessert station at Fremont Chicago.
Attend a Blackhawks game
Nothing gets the blood pumping like adult men slamming into each other at high speeds! Hockey games in Chicago are a great place to spend a winter’s day — grab a beer and cozy up under some blankets while cheering on the hometown team. Tickets start at around $40 for standing room only and $250 for center rink seats.
Visit the Starbucks Reserve Roastery
Built in 2019, this is the largest Starbucks in the world! It’s four stories tall and located right in the heart of Michigan Avenue. You can order any of Starbucks’ regular menu items, but they also offer a wide selection of gourmet coffees, food, and alcoholic drinks. Pistachio buttered rum, anyone?
Walk and shop down Michigan Ave
Michigan Avenue, also known as “the Magnificent Mile,” is one of Chicago’s main shopping streets. In the winter, the historic Water Tower and the trees along the side of the road are covered in lights. It’s a great place to take an evening stroll after dinner or shop for Christmas presents during the day.
See the Christmas tree at Millennium Park
Each year, the city of Chicago puts up a huge Christmas tree in Millennium Park (home of the Bean). The tree goes up in late November with a special tree lighting ceremony. After that, you can admire and take pictures by the tree every day through the beginning of January.
Go on a holiday-themed bar crawl
Twelve Bars of Christmas (TBOX) is a long-running Chicago Christmas tradition. From very early in the morning, you get entry to over 30 bars in Wrigleyville and can hop between them at your leisure. The best part is that everybody dresses up in wacky holiday outfits — from the Grinch to Santa Claus and everything in between. Some of the proceeds from ticket sales are also donated to charity, making this a fun and feel-good event.
Have drinks and play games at a “beercade”
For a more chill bar experience, check out Headquarters Beercade in River North. This “beercade” (beer + arcade) is filled with old-school arcade games like Pac Man and Space Invaders. It’s a super fun place to come on a lazy winter afternoon or on a first date.
Book a tour in Chicago
While it may not be a typical winter getaway, Chicago takes the cold-weather cake when it comes to fun activities. With so much to do in Chicago in the winter, you might not even miss the warmth of summer (almost). If you want some more tips and itineraries, make sure to check out some more of my travel guides!
xoxo Niki
⇉ Lake Michigan Circle Itinerary: A 7-Day Road Trip Through 4 States
Pin this post to save it for later!
Flights | I start my search on Google Flights, then usually book directly with the airline so I’m protected in case anything goes wrong.
Accommodation | Booking.com is my go-to for booking accommodation. They have an awesome cancellation policy and a super easy-to-use website.
Activities | GetYourGuide is my all-time favorite site to book day tours and activities because their cancellation policy is unmatched. Viator is another great option, especially for multi-day trips and tours.
Luggage | Carry-on only or bust! I use my Fjallraven Kanken backpack on just about every trip I take. I also love Beis for carry-on suitcases, weekender bags, and makeup/toiletry cases.
Photography | I use my iPhone 12 Pro, a Canon G7x Mark ii, and a DJI Mini 2 drone for all of my photos and videos. I also edit my photos in Lightroom.
