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10+ Reasons to Visit Chicago During the Holiday Season

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Create Chicago holiday memories with your family

A visit to Chicago is a treat for Champaign-Urbana families during any season. Over the years we have shared lots of tips and recommendations about our favorite Chicagoland destinations as well as about the logistics of travel, lodging, and — mmmmmm — eating.

To counteract the increasing chill and darkness of the rapidly approaching winter season, Chicago dials it up to 11 for the holidays. We set out to discover some big-city holiday highlights, with our own experiences mixed in with our readers.

Millenium Park Chicago Christmas tree
City of Chicago Christmas Tree in Millennium Park (photo from choosechicago.com)

As is the case most places these days, Chicago starts the official Christmas machine in mid-November with multiple lighting ceremonies. Another highlight is the Thanksgiving Day Parade that follows its traditional route along State Street in the Loop.

One of the best things about Chicago is that it offers so many budget-friendly opportunities to enjoy the season. (We love our friends in Indianapolis, but many of the city’s top holiday traditions come with a hefty price tag; for exceptions to this rule, find out when to time your visit to Indy.)

Weekends in December will be pretty insanely busy no matter where you choose to go — as is Every Single Day between Christmas Day and New Year’s Day when seemingly the entire Midwest goes on vacation and converges on Chicago’s tourist destinations.

Our readers gave plenty of advice to maximize your holiday fun:

  • Weekday visits to most of these destinations are going to be your best bet.
  • Plan ahead for any reservations you might need.
  • Look for Groupon or other deals on the more expensive options.
  • “Pick an area and make that your focus or you’ll overdo it. Determine where you want to eat, or your number one stop, and plan your outing around that.”
  • The ultimate mom advice — “Be safe & dress warm!”

We have not visited all of these locations personally. Do you have a favorite Chicago holiday tradition? Please email us.

FREE OR RELATIVELY INEXPENSIVE

Lincoln Park Zoo ZooLights: While the normally free Lincoln Park Zoo charges admission for its lights this year, the cost is relatively low ($7 per person weekdays, $10 per person weekends and special days). Mondays are free. Tickets are required each night. ZooLights will be celebrated from Nov. 17 to Jan. 7. Some days include performances or special events, such as Dec. 31, which features New Year’s Eve countdowns every hour.

ZooLights at Lincoln Park Zoo
ZooLights at Lincoln Park Zoo (photo from Facebook)

Macy’s on State Street: It’s not the holidays in Chicago without a visit to State Street to see the themed window displays, which are already up and running (they debuted the first weekend in November). This visit can be free if you simply admire the window magic and decorations in this historic store. For a holiday splurge, make a reservation to eat a fancy lunch in the Walnut Room restaurant inside the store (although at last look, reservations are already full from Nov. 18 to Jan. 1; get on the cancellation list). Of course when I was a kid, it was the Marshall Field’s windows that were the main attraction, but alas, showing my age.

Christkindlmarket: This traditional holiday market is located in Daley Plaza, not far from Macy’s on State Street, so if you head downtown — it’s easy to combine these. We’ve heard from friends that this market offers really cool crafts and artisan goods in the traditional German style, so how much money you spend on food or souvenirs is up to your family. It’s free to enter, and there’s also lots of free live entertainment — from brass bands to ballet. Check the calendar to plan your trip; open Nov. 17-Dec. 24. There is also a Christkindlmarket in Wrigleyville.

Fun at Millennium Park: Bring your own skates, and skating at Millennium Park is FREE! Remember to reserve a time online well in advance. (Also if you don’t manage to skate during the holiday season, the rink is actually open well into March). Stop by the Bean for the Millennium Park Holiday Sing-Along: sing out and celebrate Chicago’s diverse holiday traditions at 6:30 p.m. on Dec. 1, 8, 15.

Art on the Mart: An incredibly unique FREE attraction you’ll be marveling at for days. Art on the Mart is a free light show that projects art on the Merchandise Mart downtown on the Chicago River. This winter, Art at the Mart will collaborate with students from the School of the Art Institute on a new installation. 7:30 and 8 p.m. nightly; bundle up!

joffrey ballet art on the mart
Art on the Mart. Photo credit via Art on the Mart Facebook page.

The CTA Holiday Train and Bus: This holiday tradition will return for its 32nd year, from Friday, Nov. 24-Monday, Dec. 18. Check back here for more info. Consult the CTA schedule to see when a given bus or train route will feature a blinged-up ride with lights, decorations, music, and Santa. Regular transit fees apply.

Garfield Park Conservatory: A beloved oasis on Chicago’s west side, it is one of the largest and most stunning botanical conservatories in the nation, with eight indoor display gardens open year-round as well as more than 10 acres of outdoor gardens. This year’s Winter Flower Show Snow Day! (open Nov. 24 through Jan. 7) will celebrate the Garfield Park Conservatory Alliance’s 25th anniversary. Learn about the rich 25 years of history while enjoying beautiful silver foliage, lush poinsettias in pink and white hues, and more of our favorite winter flowers and plants. Admission to the Conservatory is always FREE; however timed entry reservations are required and donations are welcome.

Garfield Park Conservatory in Chicago

FUN IN ICONIC PLACES

Winterland at Gallagher Way: Features a Christkindlmarket next to Wrigley Field at Gallagher Way — entry is free and no tickets are required. For $5 per person, enter Wrigley Field and get access to a unique experience, including an ice rink inside the historic stadium! Save money by buying attraction ticket bundles in advance online. Rent a pair of skates and take a spin on the 12,000-square-foot Gallagher Ice Rink. Also: on-field games, carnival rides, an ice slide, a miniature train, and ice bumper cars. Wrigley Field activities start Nov. 17 and go through Jan. 7.

Museum of Science and Industry: Boasts a four-story, floor-to-dome Grand Tree, surrounded by a forest of more than 50 trees and displays decorated by volunteers to represent the holiday traditions from cultures around the globe. An 80-year tradition! This year’s holiday exhibits, Christmas Around the World and Holidays of Light, are included in museum entry and are open from Nov. 18 through Jan. 7. (Photo opportunities with Santa require a reservation and extra charge.)

Christmas tree at Museum of Science and Industry
Decorating at the Museum of Science and Industry (photo from Facebook)

Light Up the Lake at Navy Pier: If you prefer indoor holiday celebrations that are a bit more temperature controlled, this is the place for you. Light up the Lake offers indoor lights displays and outdoor ice skating; there seems to be something for everyone, with a mix of free and ticketed activities. You can ride on Navy Pier’s iconic 200-foot Centennial Wheel, offering 360-degree views of the decorated city and frosty Lake Michigan — it’s heated. From Nov. 24 to Dec. 31.

GO TO A SHOW

There’s no shortage of holiday-themed entertainment in Chicago. Here’s just a few of the shows on our radar for 2023:

  • The Nutcracker presented by Joffrey Ballet
  • A Christmas Carol at the Goodman Theatre
  • A Charlie Brown Christmas
  • Dr. Seuss’ How The Grinch Stole Christmas! The Musical
  • Hip Hop Nutcracker

SPECIAL FOOD AND DRINK

High Tea or Hot Cocoa: Many of our readers and their families like to indulge in High Tea for the holidays: recommendations downtown include the American Girl store, the Russian Tea Time restaurant, or the Drake Hotel. One budget-conscious reader suggested buying hot cocoa at the Starbucks located in the Palmer House Hotel, and then going up to gawk at the Palmer House holiday decor in the lobby as well as the view from the second floor.

LIGHTS AND MORE LIGHTS

We wouldn’t be Chambanamoms if we didn’t list additional holiday lights displays. Besides the downtown Chicago lights at Lincoln Park Zoo listed above, our readers also recommend lights at these suburban locations. Some of these require timed tickets, so get your reservations EARLY.

More city holiday fun: 10 Ideas for an Indianapolis Holiday Getaway

Looking for more? Subscribe to our Home for the Holidays Newsletter.  Want more ideas for holiday (or everyday) fun? Check out our Events Calendar.

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