10 Great Reasons to Visit Chicago for Winter Break

We have 10 great reasons to visit Chicago for winter break and one may make you laugh. If you are thinking about which cities to visit in Illinois, Chicago should be at the top of the list.

You might be looking for a cheap winter vacation or just decide to go somewhere you’ve never been.

Either way, here’s why we think Chicago is the best big city in Illinois for winter vacation and holiday celebrations! Chicago for winter break is a destination where cherished memories are made, leaving you with a desire to return year after year.

Why You Should Visit Chicago for Winter Break

Chicago is Rated the Second-Best City in the World

Chicagoans already know this is a great city to live in and visit. However, a recent study by Time Out has also given a stamp of approval.

Chicago was number 2 on the magazine’s list of the 53 best cities in the world.

After surveying over 20,000 readers who weighed in on important factors like nightlife, restaurants, culture, and public transportation, it’s apparent that Chicago offers the best amenities for residents and visitors.

Magical Christkindlmart

Christkindlmart at Daley Plaza is an annual holiday market that offers ethnic foods, cultural activities, and unique stalls to shop for souvenirs, gifts, ornaments, and other European-inspired items.

There are also locations in the western suburb (Aurora), and the north side of Chicago (Wrigleyville).

Chicago is a Foodie Town

Chicago is home to some of the most classic and iconic comfort foods.

Visitors from around the globe travel to this great city to eat world-famous noshes like deep dish pizza, the Chicago hot dog, and Garrett’s popcorn.

And the list doesn’t stop there! Be sure to read this post on some classic eats of Chicago! 

World Class Museums & Art

Chicago is world famous for its cultural scene in arts, coffee, festivals, and outdoor events, including Lollapalooza.

The Art Institute of Chicago is a must-see for century-old collections. Learn fascinating facts about Chicago’s past at the Chicago History Museum.

Visit the DuSable Museum of African American History to learn about the culture and account of African Americans or the Field Museum of Natural History which houses collections that originated from the 1893 World’s Columbian Exposition.

MSI Chicago and the Children’s Museums are also favorites. There is something for everyone.

Magnificent Mile Lights

Bright lights are everywhere! This annual event is a thrill for kids and adults.

The parade takes place along Chicago’s Magnificent Mile to officially kick off the official holiday season. The festival features celebrity guest appearances, Mickey Mouse, Santa Claus, and the lighting of the trees on Michigan Avenue.

It’s a fun way to get into the season’s spirit and start holiday shopping. 

✅Pssst… Here’s the newest addition of must-see attractions!
The Chicago Museum of Ice Cream

Free Things to See and Do in Chicago

Visitors will be surprised to learn all the free things to see and do in Chicago.

Among them are the Chicago Cultural Center, Navy Pier, select museums (on qualifying days), Lincoln Park Zoo, city galleries and exhibits, and much more.  

seagull standing on snow and ice

We’re Home to the Largest Starbucks in the World

Did you know that Chicago is home to the world’s largest Starbucks? Coffee lovers will be delighted to experience six floors of caffeinated heaven.

It’s the perfect stop after shopping the Mag Mile or to warm up with a cup of hot chocolate.

Read this guide to see all there is to explore at the Starbucks® Chicago Reserve® Roastery.

Chicago Transportation is Safe and it’s Easy to Get Around

Skip the rental car and hop aboard the “L” train! The lines run from O’Hare and Midway Airport and to the downtown loop.

Getting around the city is a breeze with other train lines and bus services. Get familiar with all transportation options in Chicago and get in the know before you go!

Maggie Daley Park is a Blast

Chicago’s playground is open year-round for fun and activities.

Mature trees bring the jeweled colors of fall. New facilities include a new sports complex ice rink in a ribbon loop, a climbing wall, and a children’s playground with six different areas.

And the outdoor entertainment area is next to Chicago’s Millenium Park!

Weather During the Winter Holidays Is Just Right

November is usually the first month of snowfall in Chicago, but the temperatures may still be too warm for it to stick or for the sidewalks and streets to be icy.

However, you can expect a heavier snowfall by Christmas. From November to December, the temperatures reach between 45 °F and 55 °F (7-11 °C). It’s not too hot. It’s not too cold.

The best way to dress is to wear layered clothing. 

FAQ about Chicago for Winter Break

Can you walk in Chicago in the winter?

Yes, but be prepared for the cold and wet weather. Wear boots, a warm coat, scarf, hat, and gloves.

What is Chicago like in the winter?

Chicago is very picturesque in winter with holiday lights and snow.

What is the coldest month in Chicago?


Final Thoughts on Reasons to Visit Chicago for Winter Break

As Prince, the artist who once had no name, once told Oprah his reason for moving to Minnesota “I like the cold weather, it keeps the bad people away.” That is funny, but true. The shenanigans in Chicago during Winter is much lower than warm weather seasons.

Nonetheless, visiting Chicago for winter break provides opportunities to ice skate in iconic locations like Millennium Park or Maggie Daley Park, enjoy fun winter festivals, and catch the city’s vibe under different weather conditions.

Exploring Chicago for winter break also means you won’t have to hack your way saving in non-peak season. The best winter city breaks you can find will depend highly on what you are looking for, of course.

Maybe you want snow, or maybe you want some sun. Maybe you are looking for a cheap winter break or you decided to go somewhere you’ve never been before.

Either way, here’s why we believe Chicago is the best metropolitan city in Illinois for a winter break.

Happy travels!

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  1. JJ Jordan says:

    Chiago looks like a great winter destination. I would love to visit one day!

    1. Tanya Taylor says:

      The snow makes playtime more fun in the winter. Safe travels!

  2. I’m a firm believer that just because it’s winter doesn’t mean you shouldn’t visit a place – Chicago seems magical in the winter!

    1. Tanya Taylor says:

      I couldn’t agree more — winter vacations are just as fun!

  3. I would add eat in the Walnut Room at Macy’s (previously Marshall Field’s to the list!

    1. Tanya Taylor says:

      Great choice! I have lived here for decades and although I have seen the Christmas windows many times, I’ve yet to get a reservation in the Walnut Room for Christmas…the seats go fast!