10 Reasons to Visit Chicago During the Holidays

When it comes to holiday magic, Chicago can be overshadowed by other big cities (say, ahem, for example, the one on the east coast) and overlooked as a holiday destination by out of town visitors. No fair, I say! The Windy City knows how to put on a holiday show and bring out some serious holiday spirit! Yes, temperatures can be cold here at this time of year, but the holiday splendor and cheer of our city will make for a very memorable and warm holiday experience.

Here are 10 reasons you should consider visiting Chicago during the holidays:

1. Magnificent Mile Lights Festival
It can be crowded and a bit crazy, but this is the official start of the holiday season in Chicago and our city’s version of the Macy’s Parade. The Magnificent Mile Lights Festival is known for its tree-lighting procession down Michigan Avenue, led by none other than Mickey Mouse and Minnie Mouse and even includes fireworks. Enough said.

Christmas things to do in Chicago - Magnificent Mile Light Festival
A fireworks display over the Chicago River is the grand finale of the Magnificent Mile Light Festival.

2. Festive City Skyline
Every holiday season, major Chicago landmark buildings such as the Hancock, Willis Tower and many others dress up in signature red and green lights making for awesome Instagram photos!

3. ZooLights
Chicago’s beloved Lincoln Park Zoo, conveniently located close to downtown, puts on a FREE spectacular display of lights throughout its grounds and hosts several fun holiday themed activities every holiday season. My personal favorite aside from the lights: amazing ice-sculpture carvers. (This is the one occasion when you will want it to be very cold outside!)

Christmas things to do in Chicago - ZooLights ice carvers
Aside from the spectacular light display, ice-sculpture carvers are one of the main ZooLights attractions.

4. Ice Skating Next to the Bean
When you are done taking pictures at the famous Bean sculpture in Millennium Park, you can practice toe loops and double axles at the McCormick Tribune Ice Rink, just steps away. For novices or those in need of a refresher, there are free skating lessons, offered Friday through Sunday one hour before the rink opens. When you are ready to take a break, pop into the Park Grill Café for hot chocolate.

Insider Tip: Visit on Friday night to catch the part concert, part sing-along Christmas caroling by local choral groups in front of the Bean. Holiday spirit galore guaranteed!

Christmas things do in Chicago - McCormick Tribune Ice Rink at the Millennium Park
The McCormick Tribune Ice Rink at Millennium Park.

5. Window Shopping at Macy’s
The Macy’s store on State Street takes window shopping to a new level with its holiday windows. A Chicago tradition, originated in 1897 by the Marshall Field and Company, it has been fortunately retained by its new owner who took over in 2006. Splendidly decorated, the windows tell a story as you walk outside from one end of the building to the other. To kick it up a notch, visit the Walnut Room on the 7th floor, said to be the very first department store restaurant in the country and gloriously decked out this time of year.

Christmas things to do in Chicago - Macy's Holiday Window Story Display
The theme of this year’s Macy’s holiday window story display on State Street is “Santa’s Journey to the Stars.”

6. Authentic German Christmas Market
The lines for the German sausages and gluhwein can be long, but they’re worth it. They are delicious, the real deal (having lived in Nuremberg, I can attest) and can be found at Christkindlmarket, Chicago’s traditional German holiday market located at the Daily Plaza. When you are done sampling the goodies, you can marvel at the sky-high Christmas tree, do some Christmas shopping and get a quick picture with Santa. Being a Mom, I’m all for multi-tasking, especially during the busy holiday season!

Christmas things to do in Chicago - Christkindlmarket Daley Plaza
The Christkindlmarket at Chicago’s Daley Plaza offers great food and unique Christmas shopping.

7. Holiday Theater
We might not have Broadway (though we do have a street with this name), but Chicago’s holiday theater scene can rival that of New York. From the Geoffrey Ballet Nutcracker spectacular to a long list of excellent holiday-themed theater shows, the only challenge you will have is which one to chose. One show our family recommends in particular is the original, poignant and modern version of The Nutcracker at the House Theater. It’s worth ubering over to Chicago’s Bucktown!

Christmas things to do in Chicago - The Nutcracker Show at the House Theater
The Nutcracker audience at the House Theater participates in a make believe snow fight during intermission.

8. Holiday Tea at the Drake Hotel
Ah, the splendor, the lavish decorations, the graceful harpist, the joyful Twelve Days of Christmas carolers and, of course, the irresistible holiday pastries! A holiday institution for many Chicagoans and visitors in-the-know, Holiday Tea at the iconic Drake Hotel is much more than “just the tea,” it’s the holidays!

Christmas things to do in Chicago - Holiday Tea at The Drake Hotel
Holiday Tea at the Palm Court of The Drake Hotel on Michigan Avenue is a holiday tradition for many Chicagoans and visitors alike.

Read More>> Holiday Tea at The Drake Hotel in Chicago

9. Christmas Around the World
Want to see how Christmas trees are decorated in Guatemala, Slovenia, Japan or India? You won’t need your passport, just head to Chicago’s Museum of Science and Industry to see its popular Christmas Around the World and Holidays of Light exhibit and gain a perspective on other cultures and holiday traditions. The beautiful display of trees is decorated with help of volunteers from the city’s many ethnic communities.

Christmas things to do in Chicago - Christmas Around the World exhibit at the Museum of Science and Industry
The Christmas tree representing Guatemala at the Christmas Around the World and Holidays of Light exhibit at the Museum of Science and Industry.

>>Read More: Chicago Museums with Great Holiday and Winter Themed Exhibits

10. The Holiday Train, Chicago’s version of the Polar Express
Riding the Chicago “L” train is a unique and authentic experience year round, but catching a ride on the bedazzled Holiday Train which runs every year during the holidays is simply magical and unforgettable. Check out the CTA website for more information and this year’s schedule and then line up for the first car so you can “Ho Ho Ho” with Santa who sits, where else, up front.

Christmas things to do in Chicago - Santa, leading the Holiday Train
Santa, leading the Chicago Holiday Train.

You may also enjoy:

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Know Before You Go

  • Chicago’s nickname is “The Windy City.”
  • Make sure to visit Millennium Park so that you can see the world-famous Bean!
  • Avoid visiting in the winter if you aren’t a fan of cold weather! The weather warms up around May.

Oak Street Beach in Chicago photo by Jrissman – Own work. Licensed under CC BY-SA 3.0 via Commons.

This post was written by Hilton Suggests Team Member, Vera H. Are you interested in traveling to Chicago? Let us know if we can help you with any other recommendations. Tweet us for more great local travel tips!

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