What to Do in Chicago Over Winter Break

Finals are almost over, which means winter break is right around the corner! There’s so much to do (if you can get past how miserably cold it is), which is why Chicago is the perfect place to spend your holiday. Not only is the city lit up with gorgeous holiday lights, there are a ton of things to see and do that you can only get here in a Chicago winter. So, if you’ll be staying here these few weeks, make sure you don’t miss out on these winter faves!

As a bonus, I’ve included pro tips for each recommendation. I’ve lived in Chicago my whole life, and done all of these more times than I can count. That means that not only is this list made up of what I’ve learned are the ~best of the best~ BUT I have included pro tips will make your experience even better. The Maggie Daley

Ice Skating Ribbon – Maggie Daley Park

In the heart of downtown with the most scenic view of the city sits the Maggie Daley Park ice skating ribbon. With the city skyline as your backdrop, this is truly a memorable skating experience. Add to that the uniquely swirly shape of the trail, and you’ll experience ice skating like you never have before. So, grab a hot chocolate, lace up your skates, and enjoy what Chicagoans call an “alpine in the city.”

Pro Tip: admission to the skating rink is free, but renting skates and a locker can cost $16 - $20, so plan accordingly. 

The Lincoln Park Zoo


Enjoy one of the oldest zoos in the United States at its brightest time of year -- the entire park literally lights up with thousands of holiday lights. With life-sized light versions of zoo animals, lights that climb their way up the trees, and more, ZooLights is a Chicago tradition that cannot be missed. Enjoy fun activities such as photos with Santa, ice-sculpture carving, a musical lights display, and more while wandering through the exhibits. ZooLights are the perfect way to put yourself in the holiday spirit while staying close to school -- it’s a quick walk from DePaul’s LPC.

Pro Tip: The Lincoln Park Zoo does a special New Year’s Eve party with their ZooLights so if you don’t yet have any plans, I recommend braving the cold and ringing in 2020 in wild style! Get in my belly

Take a Trip to Cocoa + Co.

If you’re feeling a bit chilled after ZooLights, stop by the nearby Cocoa + Co for a heartwarming cup of hot chocolate. With a menu full of thick drinking chocolates, spiced warm beverages, and seasonal drinks to fit your taste buds at all times of the year, Cocoa + Co won’t just warm your body, it’ll warm your soul. The perfect cozy space to snuggle up with a hot drink and chat with your friends for a while, Cocoa + Co is must during the cold Chicago winter.

Pro Tip: Get the special holiday hot chocolate. Not only is it delicious, but it comes in a cute holiday mug and is unique to the winter season! Christkindlmarket!


Modeled after the Christmas markets in Germany and offering traditional German candies, glühwein, and handmade gifts, Christkindlmarket is a must-see year after year. Every year, this market takes over the Daley Center with shops pushed up one against the other. The smell of baked goods and candied nuts wafts through the packed walkways while the sound of happy holiday chatter takes over the air. Not only is this the place to find some new favorite holiday foods, it is the perfect way to start your holiday season. And with a new glühwein mug design every year, you won’t want to skip this.

Pro Tip: Go during the last hour of a weekday towards the beginning of the run. It’s way less crowded, so you’ll be sure to get the most out of your experience.  For those 21+

 Frosty’s Christmas Bar

One of the largest Christmas pop-up bars in the city, Frosty’s is a Christmas present all its own. With three-levels and four bars, Santa as the DJ, themed cocktails, and holiday movies, this is the perfect combination of childhood holiday magic and adult Christmas experience. Not to mention, if you’re worried your decorations at home aren’t enough, this is the place to snap some perfect holiday instagrammable pics.

Pro Tip: Aren’t in town over break? This Christmas themed bar keeps the holiday spirit until January 5th!


The Art Institute of Chicago

Warm up this winter while enjoying some fantastic art. The Art Institute of Chicago is one of the oldest and largest museums in the US. With well-known classics, popular modern pieces, and a constantly changing selection of temporary exhibitions, the Art Institute has something for everyone, and you’ll get to see something new every time you go. In the heart of downtown, the Art Institute is easy to get to so you can minimize the amount of time you spend outdoors. So, take a break at the perfect escape from the cold Chicago weather.

Pro Tip: DePaul students get tear-round free admission, so definitely take advantage of this while you’re still a student!

Multicultural festivities! 

“Christmas Around the World” at the Museum of Science and Industry

Ever wondered how other cultures celebrate their holidays? Well now you can find out! Explore the celebrations and traditions of other cultures at the Museum of Science and Industry’s Christmas Around the World exhibit. With live performances, a four story grand tree, and more than 50 displays, this holiday exhibit will keep you captivated for hours, and maybe teach you a thing or two.

Pro Tip: This holiday exhibit is included in the price of general admission to the museum!