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43 Cozy Things to do in Chicago in the Winter (a Local’s Guide)

43 Cozy Things to do in Chicago in the Winter (a Local’s Guide)

43 Cozy Things to do in Chicago in the Winter (a Local’s Guide)
The Windy City is a winter wonderland this time of year. From ice skating at Millennium Park to sipping mulled wine at a real Christmas Market, find out how you can enjoy all that Chicago has to offer during the coldest season of the year. Don't forget about deep dish pizza and holiday cheer!

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Sparkling Christmas lights. Real German Christmas markets. Deep dish pizza – and deep snow. Chicago might not be known for its, shall we say, balmy winters, but there are many intrepid locals and visitors who embrace the blistering cold winds and snow-covered sidewalks!

Winter in Chicago is the best time traipse through shimmering holiday lights with a mug of hot mulled wine, glide around one of the city’s many outdoor ice rinks, or cozy up in a museum cafe. Besides, everyone knows hot chocolate tastes better while walking down snow-covered streets!

We tapped a local to create this guide to all the best things to do in Chicago in the winter. Take it away, Allison!

Chicago At-a-Glance ✍

Here’s a bite-sized snapshot of everything you need to know to plan your trip!

Psst: Planning more travels around the midwest? We’ve got some posts that may help! Check these out:

Need some help packing for your trip? Sign up below and we’ll send a printable cold weather packing list straight to your inbox!

Printable Winter Packing List

This FREE 3-page printable packing list will help make sure you don’t forget anything for your next winter trip. We’ll also send you our favorite travel tips!

A sunny winter day overlooking Millennium Park and skyscrapers in Chicago, Illinois
The snow-lined banks of Millenium Park and the iconic Bean statue!

Winter in Chicago FAQs

You probably have some questions about Chicago in the winter. Namely, “am I going to freeze to death?” or “wait, what do you mean the Windy City isn’t called that because of the wind?”

Well, I can’t answer all of your questions (this article will help, though) but I can answer a few of the things you’ll need to know before planning your trip to the Arctic Chicago in the winter.

How cold is Chicago in the winter?

Winter in Chicago starts anywhere from late October and lasts until at least March and sometimes beyond. Temperatures usually range from the teens to the thirties, but you can expect it to be cold

And sometimes, really cold. Like, we-made-the-news-in-Germany-cold. In January 2019 the city bundled up for a Polar Vortex causing a record temperature of -23°. Blame the “Lake Effect.“

Besides the frigid, toe-curling temperatures, lake-effect snow makes frequent appearances between December and March, and snowstorms have been known to fall even in the Fall and Spring. If you’re coming from a place that doesn’t get snow, get excited: I can’t guarantee anything, but the chances of snowflakes swirling all around you while walking through a winter wonderland are very high.

But the good news is there’s a joke among locals: if you don’t like the weather, don’t worry. It’ll change in five minutes! The notorious four-seasons-a-day weather means that sure, winter can suck, but you might have a 45° day in January and a 30° day in June.

While in general highly unpredictable, the harshest months are still typically January and February. You should be prepared for any and all seasons that the Windy City might impose upon you, so pack accordingly! 

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A Chicago Transit Authority train going through snow in daytime in Chicago, Illinois
Take the “El” is a right of passage while in Chicago! (Photo Credit)

How do I get around Chicago?

The cheapest and most efficient way to get around is by using the city’s public transportation, namely the train system called the “El” (for elevated train) and bus system. Visitors can purchase one-day, seven-day, and 30-day passes from the Chicago Transit Authority (CTA). 

If your visit happens to fall on an unseasonably warm and pleasant day, you can also opt to transit by river using the Chicago Water Taxi or Divvy, the bike-sharing system offering both standard and electric bikes. Walking—regardless of the weather— is always a great way to admire the city. 

Driving tends to be a hassle (especially when it snows!) and comes with hefty parking fees, so leave your car at home (or at your accommodation). Of course, Taxis and ridesharing like Uber and Lyft are widely available in Chicago as well.

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Giordano's Pizza in the Winter in Chicago, Illinois
Lia here: I may not be a local, but I just want to say that Giordano’s deep dish pizza is the best pizza I’ve ever had in my entire life. I am fully braced for angry comments from Chicagoans with strong opinions!

What is Chicago known for?

Chicago is an international city of immigrant enclaves and a world-renowned culinary scene. 

But before any Chicagoans have the chance to tell you how many Michelin-star restaurants we boast, the Algonquian Indigenous people called this swampy, low-lying plot of land “Checagou” after the smelly wild plants (some say leeks, others say onions) that grew in this region.

When the first non-Indigenous settler Haitian Jean Baptiste Point du Sable—for whom Chicago’s lakefront thoroughfare was recently renamed—arrived in the area in 1779, Chicago was a trading hub and home to the Potowatomi, Miami, and Illinois Native nations. 

Over time, Chicago would become a manufacturing powerhouse and could come to be known as “The Second City,” a nickname that actually has nothing to do with the population (though it is the third largest city in the U.S., after New York and Los Angeles). According to some, it’s because it has always competed against New York, and many others point to the fact that the Great Chicago Fire of 1871—the largest urban fire in history—was devastating, but gave the metropolis a clean slate to rebuild for a second time (and a huge reason we have so many brick buildings—fire safety!). 

Because of that catastrophe, Chicago dared to be innovative and today still houses some of the most impressive architecture in the world. Combine our cutting-edge design with the city’s deep dish pizza (love it or hate it!), improv comedy, fervent sports fans, and rich African-American history, visitors will quickly see that culture happens here year-round. 

A view of Cloud Gate or the Bean in Millennium Park on a snowy winter day in Chicago, Illinois
The “bean” reflects snow so beautifully in the cold wintertime. (Photo Credit)

Things to do in Chicago in the Winter

As tempting as it may be to curl up and watch Netflix in the winter, Chicagoans bundle up and brace themselves to get out and explore. With so much fascinating architecture, seemingly endless food and drink options, holiday surprises, and some of the best entertainment in the country, this city has no excuse to stay home. 

Explore Chicago’s Downtown, called “The Loop”

Named for the El’s circular pattern around the city’s commercial and business district, the Loop is an area of the city that’s heavily trafficked by visitors and professionals and avoided by many locals. Still, it holds important cultural and historical context and is worth spending time in. Here are a few things you should do when you’re in the area:

  • Head to the top of the world’s tallest building (well, it was until 1998). The Willis Tower (referred to by locals as “Sears Tower”) stands at 110 stories high. The building’s Skydeck offers impressive views of the city and Lake Michigan. If you’re not afraid of heights, walk out onto the glass ledge with its glass floor and stare down at the over 1,300 feet below you. On a snowy day, you can see a winter wonderland for miles around and feel like you’re in a real-life snowglobe!
  • Buy a Chicago City Pass to explore the top downtown museums and experiences. This is perfect if you want to experience the snowy Skydeck and see tropical fish at the Shedd Aquarium.   
  • Walk the sculpture garden and grounds of the Loop’s green spaces, including Grant Park. You’ll find art, architecture, and iconic buildings constructed for the 1893 World’s Columbian Exposition. 
  • Envision what the “vice district” was like when famous gangster Al Capone roamed the city in the 1920s and 1930s on this history and ghost walking tour.
  • Take a selfie at Millenium Park’s Cloud Gate, the large, reflective sculpture locals refer to as “the bean.” 
  • Take this food, architecture, and history tour of the Loop for some of the best views, historical context, and culinary treats the area has to offer. You’ll marvel at the stunning Chicago skyline and discover why Chicago’s architecture is among the best in the world, discover why locals have so much passion for their Chicago-style classics, try a couple of classic made-in-Chicago snacks like Chicago-style popcorn and homemade chocolate, and get a taste for the city’s most famous food in a historic neighborhood!

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Tree lights and traditional stands at the German Christkindlmarkt Christmas market in Chicago, Illinois
Skating, Christmas lights, and a real Christmas market make for a great holiday visit! (Photo Credit: Guy Bauer)

Go to a (Legit) Christmas Market

One of the best things to do in Chicago in the winter is to soak up Holiday cheer at its two European-inspired Christmas markets! Grab a fresh pretzel or a bratwurst and a mug of Glühwein and stroll underneath the sparkling Christmas lights in the center of Chicago as cheerful Christmas music and the scent of roast nuts wafts through the air.

The Christkindlmarkts are some of the best, most authentic, and only legit Christmas Markets in the USA – so even if you can’t make it to Germany this year, you can get pretty darn close.

There are two Christmas Markets in Chicago in the winter, each open from around mid-November:

  • Christkindlmarkt in Daley Plaza: The largest Christmas Market in Chicago is the Christkindlmarkt. The market is a long-standing German-inspired local holiday favorite in downtown’s Daley Plaza. Grab a glass of the mulled wine and stroll under twinkling lights down aisles of vendors selling handcrafted goods and irresistible foods like sausages, raclette and cookies! The market closes on Christmas Eve.
  • Christkindlmarkt in Wrigley Square: During the holidays, Wrigley Square turns into “Winterland at Gallagher Way,” including a charming (if on the small side) Christkindlmarket, Santa’s Workshop, wreath-making classes, holiday movies, ice bumper cars, and ice skating! Stroll through the candy cane-striped wooden huts with a mug of hot spiced wine (Glühwein) and shop for local delicacies and hand-crafted ornaments. The market closes on New Year’s Eeve.

Celebrate the Holidays, Chicago style 

It’s barely November when Chicago decides it’s ready to get into the holiday spirit – which is good, because it’s already cold!

Here are some of the best ways to celebrate: 

  • See the holiday sights: This three-hour holiday walking tour takes you through Millennium Park and other iconic locations in The Loop to see its dazzling Christmas tree and ice-skating rink. Along the way, you’ll also be enjoying brownies, hot apple cider, and some Chicago classics: pizza and hot dogs!
  • Admire twinkling holiday lights: You know what gets me hyped for Christmas? Heading to Zoo Lights at the Lincoln Park Zoo! From mid-November through New Year’s you can visit this dazzling experience on the zoo’s grounds. We’re talking rainbow tunnels, giant trees made out of dazzling lights, and thousands of twinkling holiday cheer everywhere. You’ll also be able to snack on some holiday treats and even sip wine as you make your way through the festivities. 
  • Shop (or window shop): Shopping districts like the Magnificent Mile and along State Street are decked out in elaborate light displays and window decorations. The famous Macy’s windows have a different theme each year which they’ve been doing since 1870(!) and their Walnut Room—the first-ever restaurant in a department store—features an impressively large Christmas tree. 

Travel Tip: Make sure to take public transportation during the holidays— you might catch one of the CTA’s special Santa-driven trains and festive buses!



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