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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Glowing Christmas lights. Actual German Christmas markets. Deep dish pizza – and deep snow. Chicago may not be identified for its, let’s consider, balmy winters, however there are a lot of intrepid locals and guests who embrace the blistering chilly winds and snow-covered sidewalks!

Winter in Chicago is the most effective time traipse by way of shimmering vacation lights with a mug of scorching mulled wine, glide round one of many metropolis’s many outside ice rinks, or cozy up in a museum cafe. Moreover, everybody is aware of scorching chocolate tastes higher whereas strolling down snow-covered streets!

We tapped an area to create this information to all the most effective issues to do in Chicago within the winter. Take it away, Allison!

Chicago At-a-Look ✍

Right here’s a bite-sized snapshot of every little thing you’ll want to know to plan your journey!

Psst: Planning extra travels across the midwest? We’ve acquired some posts that will assist! Examine these out:

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Printable Winter Packing Listing

This FREE 3-page printable packing record will assist ensure you do not forget something in your subsequent winter journey. We’ll additionally ship you our favourite journey suggestions!

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

Winter in Chicago FAQs

You most likely have some questions on Chicago within the winter. Particularly, “am I going to freeze to loss of life?” or “wait, what do you imply the Windy Metropolis isn’t referred to as that due to the wind?”

Effectively, I can’t reply all of your questions (this article will assist, although) however I can reply just a few of the belongings you’ll have to know earlier than planning your journey to the Arctic Chicago within the winter.

How chilly is Chicago within the winter?

Winter in Chicago begins wherever from late October and lasts till at the least March and typically past. Temperatures often vary from the teenagers to the thirties, however you may anticipate it to be chilly

And typically, actually chilly. Like, we-made-the-news-in-Germany-cold. In January 2019 the town bundled up for a Polar Vortex inflicting a report temperature of -23°. Blame the “Lake Effect.

Moreover the frigid, toe-curling temperatures, lake-effect snow makes frequent appearances between December and March, and snowstorms have been identified to fall even within the Fall and Spring. In case you’re coming from a spot that doesn’t get snow, get excited: I can’t assure something, however the possibilities of snowflakes swirling throughout you whereas strolling by way of a winter wonderland are very excessive.

However the excellent news is there’s a joke amongst locals: if you happen to don’t just like the climate, don’t fear. It’ll change in 5 minutes! The infamous four-seasons-a-day climate implies that certain, winter can suck, however you might need a forty five° day in January and a 30° day in June.

Whereas normally extremely unpredictable, the harshest months are nonetheless usually January and February. You need to be ready for any and all seasons that the Windy Metropolis may 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 proper of passage whereas in Chicago! (Photo Credit)

How do I get round Chicago?

The most cost effective and most effective solution to get round is by utilizing the town’s public transportation, specifically the prepare system referred to as the “El” (for elevated prepare) and bus system. Guests can buy one-day, seven-day, and 30-day passes from the Chicago Transit Authority (CTA)

In case your go to occurs to fall on an unseasonably heat and nice day, you may also decide to transit by river utilizing the Chicago Water Taxi or Divvy, the bike-sharing system providing each customary and electrical bikes. Strolling—whatever the climate— is all the time an effective way to admire the town. 

Driving tends to be a trouble (particularly when it snows!) and comes with hefty parking charges, so go away your automotive at dwelling (or at your lodging). After all, Taxis and ridesharing like Uber and Lyft are extensively obtainable in Chicago as effectively.


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Giordano's Pizza in the Winter in Chicago, Illinois
Lia right here: I will not be an area, however I simply need to say that Giordano’s deep dish pizza is the most effective pizza I’ve ever had in my complete life. I’m totally braced for offended feedback from Chicagoans with sturdy opinions!

What’s Chicago identified for?

Chicago is a world metropolis of immigrant enclaves and a world-renowned culinary scene. 

However earlier than any Chicagoans have the prospect to inform you what number of Michelin-star eating places we boast, the Algonquian Indigenous people referred to as this swampy, low-lying plot of land “Checagou” after the smelly wild vegetation (some say leeks, others say onions) that grew on this area.

When the primary non-Indigenous settler Haitian Jean Baptiste Point du Sable—for whom Chicago’s lakefront thoroughfare was lately renamed—arrived within the space in 1779, Chicago was a buying and selling hub and residential to the Potowatomi, Miami, and Illinois Native nations. 

Over time, Chicago would turn into a producing powerhouse and will come to be referred to as “The Second Metropolis,” a nickname that really has nothing to do with the inhabitants (although it’s the third largest metropolis within the U.S., after New York and Los Angeles). In line with some, it’s as a result of it has all the time competed towards New York, and lots of others level to the truth that the Nice Chicago Fireplace of 1871—the biggest city fireplace in historical past—was devastating, however gave the metropolis a clear slate to rebuild for a second time (and an enormous cause we now have so many brick buildings—fire safety!). 

Due to that disaster, Chicago dared to be modern and right now nonetheless homes among the most spectacular structure on the earth. Mix our cutting-edge design with the town’s deep dish pizza (like it or hate it!), improv comedy, fervent sports activities followers, and wealthy African-American historical past, guests will rapidly see that tradition occurs right here year-round. 

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

Issues to do in Chicago within the Winter

As tempting as it might be to curve up and watch Netflix within the winter, Chicagoans bundle up and brace themselves to get out and discover. With a lot fascinating structure, seemingly infinite food and drinks choices, vacation surprises, and among the greatest leisure within the nation, this metropolis has no excuse to remain dwelling. 

Discover Chicago’s Downtown, referred to as “The Loop”

Named for the El’s round sample across the metropolis’s industrial and enterprise district, the Loop is an space of the town that’s closely trafficked by guests and professionals and averted by many locals. Nonetheless, it holds essential cultural and historic context and is value spending time in. Right here are some things you must do while you’re within the space:

  • Head to the highest of the world’s tallest constructing (effectively, it was till 1998). The Willis Tower (referred to by locals as “Sears Tower”) stands at 110 tales excessive. The constructing’s Skydeck gives spectacular views of the town and Lake Michigan. In case you’re not afraid of heights, stroll out onto the glass ledge with its glass ground and stare down on the over 1,300 ft under you. On a snowy day, you may see a winter wonderland for miles round and really feel such as you’re in a real-life snowglobe!
  • Purchase a Chicago City Pass to discover the highest downtown museums and experiences. That is good if you wish to expertise the snowy Skydeck and see tropical fish on the Shedd Aquarium.   
  • Stroll the sculpture backyard and grounds of the Loop’s inexperienced areas, together with Grant Park. You’ll discover artwork, structure, and iconic buildings constructed for the 1893 World’s Columbian Exposition
  • Envision what the “vice district” was like when well-known gangster Al Capone roamed the town within the Twenties and Thirties on this history and ghost walking tour.
  • Take a selfie at Millenium Park’s Cloud Gate, the massive, reflective sculpture locals check with as “the bean.” 
  • Take this food, architecture, and history tour of the Loop for among the greatest views, historic context, and culinary treats the realm has to supply. You’ll marvel on the beautiful Chicago skyline and uncover why Chicago’s structure is among the many greatest on the earth, uncover why locals have a lot ardour for his or her Chicago-style classics, strive a few traditional made-in-Chicago snacks like Chicago-style popcorn and selfmade chocolate, and get a style for the town’s most well-known meals 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 an actual Christmas market make for an awesome vacation go to! (Picture Credit score: Guy Bauer)

Go to a (Legit) Christmas Market

Top-of-the-line issues to do in Chicago within the winter is to take in Vacation cheer at its two European-inspired Christmas markets! Seize a contemporary pretzel or a bratwurst and a mug of Glühwein and stroll beneath the glowing Christmas lights within the heart of Chicago as cheerful Christmas music and the scent of roast nuts wafts by way of the air.

The Christkindlmarkts are among the greatest, most genuine, and solely legit Christmas Markets within the USA – so even if you happen to can’t make it to Germany this yr, you may get fairly darn shut.

There are two Christmas Markets in Chicago within the winter, every open from round mid-November:

  • Christkindlmarkt in Daley Plaza: The most important Christmas Market in Chicago is the Christkindlmarkt. The market is a long-standing German-inspired native vacation favourite in downtown’s Daley Plaza. Seize a glass of the mulled wine and stroll below twinkling lights down aisles of distributors promoting handcrafted items and irresistible meals like sausages, raclette and cookies! The market closes on Christmas Eve.
  • Christkindlmarkt in Wrigley Sq.: Through the holidays, Wrigley Sq. turns into “Winterland at Gallagher Way,” together with a captivating (if on the small aspect) Christkindlmarket, Santa’s Workshop, wreath-making lessons, vacation motion pictures, ice bumper vehicles, and ice skating! Stroll by way of the sweet cane-striped picket huts with a mug of scorching spiced wine (Glühwein) and store for native delicacies and hand-crafted ornaments. The market closes on New Yr’s Eeve.

Rejoice the Holidays, Chicago model 

It’s barely November when Chicago decides it’s able to get into the vacation spirit – which is sweet, as a result of it’s already chilly!

Listed here are among the greatest methods to have a good time: 

  • See the vacation sights: This three-hour holiday walking tour takes you thru Millennium Park and different iconic places in The Loop to see its dazzling Christmas tree and ice-skating rink. Alongside the way in which, you’ll even be having fun with brownies, scorching apple cider, and a few Chicago classics: pizza and scorching canine!
  • Admire twinkling vacation lights: You realize what will get me hyped for Christmas? Heading to Zoo Lights at the Lincoln Park Zoo! From mid-November by way of New Yr’s you may go to this dazzling expertise on the zoo’s grounds. We’re speaking rainbow tunnels, big timber made out of dazzling lights, and 1000’s of twinkling vacation cheer all over the place. You’ll additionally have the ability to snack on some vacation treats and even sip wine as you make your method by way of the festivities. 
  • Store (or window store): Procuring districts just like the Magnificent Mile and alongside State Road are decked out in elaborate gentle shows and window decorations. The well-known Macy’s home windows have a different theme each year which they’ve been doing since 1870(!) and their Walnut Room—the first-ever restaurant in a division retailer—options an impressively massive Christmas tree. 

Journey Tip: Be sure to take public transportation throughout the holidays— you may catch one of many CTA’s special Santa-driven trains and festive buses!


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