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Top Things to do in Chicago in the Winter

Take advantage of the chilly season in the Windy City.

a traveler in front of the Bean in Chicago

As a native Chicagoan, if I were to list my least favorite things about living in this city, the Chicago winters would be at the top of the list. Our proximity to Lake Michigan (or simply “the Lake” if you live here) is truly one of my favorite things about the city, but it makes our winters extra damp and blustery. It’s very easy to look at a Chicago winter and simply want to hibernate.

But that doesn’t sound like any fun at all! Here are a bunch of great things to do in the Windy City in its windiest season.

#1 - Visit a Museum

Winter is the perfect season to visit Chicago’s amazing museums. From the museum campus’s Shedd Aquarium and Field Museum, to the Art Institute in the Loop, these institutions are the perfect place to explore the best of Chicago while admiring views of the city from the warm side of a window. All these sites are set up with rentable lockers or coat checks, so you can bundle up for your journey to the front door, and then leave all your heavy things behind as you explore. And if your visit coincides with the winter holidays, you might see these city icons decked out in their holiday finery!

For my full guide to the Chicago Museum Campus, click Here. For a detailed guide to the Art Institute of Chicago, click Here.

#2 - Ice Skate in the Loop

Ice skating is an iconic winter pastime, so why not go skating at one of the most beautiful rinks in the country?? The Maggie Daley Skating Ribbon is a beautiful meandering loop of an ice rink with beautiful views of downtown Chicago. Skates and lockers are available for rent, and tickets are cheapest if you reserve them online ahead of time. And sure, there’s a rink in Millennium Park too, but Chicago experts know that the Ribbon is the way to go!

the Chicago skyline in winter

#3 - Visit the Landmarks

Chicago does experience a sharp drop in tourism in the winter months, especially in January and February. So if you’re looking to visit the Willis Tower (cough cough Sears Tower) or any of Chicago’s other landmark attractions, a winter visit is a surefire way to beat the crowds. Some of these attractions have lower winter rates too!

#4 - The Lincoln Park Zoo

You have to be willing to bundle up for this one, but Chicago’s #1 free attraction doesn’t slow down one bit in winter! The cooler weather even means that some animals, like the polar bears and penguins, are way more active than usual. Combine that with the heated buildings (The Small Mammals Building, the African Adventure, the Lion House, just to name a few…) and you can have an amazing winter visit to this zoo. And while you’re there, drop in on the (also free) Lincoln Park Conservatory right next door for a quick trip to the tropics!

Click Here for a full Lincoln Park Zoo guide!

a honey latte from Goddess and the Baker

#5 - Visit a Coffee Shop

Nothing makes me feel cozier in the winter than a nice cup of coffee and a warm pastry. Gather up your friends, or pack your favorite new book, and chase away your winter blues with a warm atmosphere and a cup of something hot and caffeinated. Try Cafe Urbano for horchata lattes, or Goddess and the Baker for specialty pastries, or Charmer's for the best Chai Latte in the city!

Click Here for a local's guide to the best coffee shops in Chicago!

#6 - Get Some Comfort Food

As the true Midwestern metropolis, we know how to do comfort food! Chicago’s melting pot of nationalities plus our midwestern sensibilities creates the ultimate in cozy winter dining. Pick one of these delicious spots and cozy up with a pint and a plate of something warm and melty.

There's no Shortage of Things to do in Chicago, even in the Winter!

Grab that winter jacket and a fun hat and get exploring!

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Love and Shenanigans,


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