Chicago Christmas Tree at Daley Plaza

Chicago is one of the best cities to visit around the holidays. I often find myself venturing back to the area as there is so much to do in terms of holiday entertainment and attractions. Plus, the wintry weather really adds to the holiday ambiance! Nothing really compares to bundling up with a hot cocoa in hand, snowflakes falling all around you, as you take in the festive lights of the season.

There are endless ways to keep yourself busy during the holidays. A few of my must do’s each holiday season include heading downtown to see the annual Christmas tree and browsing for unique ornaments at Christkindlmarket in Daley Plaza, holiday shopping on Michigan Ave., seeing the iconic Macy’s holiday window displays, heading over to Lincoln Park Zoo’s ZooLights event, and ice skating at Millennium Park.

The history of the Chicago Christmas tree

Chicago Christmas tree history

The first Christmas tree was lit in 1913 on Christmas Eve in Grant Park. For many years (1956-2015), the tree was located at Daley Plaza near Christkindlmarket, rated one of the top holiday markets outside of Europe. Today, the tree stands tall in Millennium Park (and has done so since 2015). At 60+ feet, it is one of the tallest Christmas trees in the country. And the beautiful architecture surrounding the tree creates a holiday setting unlike anywhere else in the country! Seeing the tree has become a yearly tradition for both locals and recurrent tourists. 

Read more about the history of the Chicago Christmas tree

Chicago Holiday Activity Bucket List

Ice skating rink at Millennium Park is one of my favorite winter/holiday activities in the city! Look at the gorgeous city views in the background! Holiday music and lights, as well as the chance of snow, creates the most magical Christmas in the City ambiance! Admission is free (one of the only rinks to offer free skating), so if you have your own skates you are ready to go! Even better, the city offers free skating lessons 9-10am Saturdays and Sundays (advance registration required).

Ice rink at Millenium Park in Chicago

Seeing the Macy’s on State Street holiday window displays is always a must-do during the holiday season. They are conveniently located just a short walk from Chriskindlmarket. Seeing the creative windows has been a defining holiday experience in the city since way back in the 60’s, when Macy’s was still Marshall Fields. Although the windows are not nearly as whimsical as they once were, fans of the beloved Marshall Fields holiday window tradition continue to make the trek downtown for this nostalgic holiday attraction. Also be sure to dine inside the gorgeous Walnut Room, a 7th floor restaurant in Macy’s known for its’ giant 45 foot tall tree and beautiful Christmas decor. Just another holiday tradition in the Windy City not to miss out on! 

Update: There are now a number of festive ice rinks downtown. Consider skating on the highest ice rink in the world on the top floor of the John Hancock Observatory. The unique ribbon shaped rink at Maggie Daley Park is also pretty fantastic.

Macy's holiday window displays - Chicago

I like to stop and take a break from shopping in the blustery cold with a nice hot cocoa! Not surprisingly, there are tons of different places to check out. A lot of tourists love the Hershey’s & Ghiradelli shops as they have cute decor and tons of cute little trinkets and gifts. Update: Hershey’s is now closed. Check out the Chicago Tribune’s list of the 12 best hot chocolates in the city!

Hershey's Chicago

Water Tower Place, along the Magnificent Mile, is always a fun spot for holiday shopping. Plus, there’s 7 floors to explore so you can literally walk around here all afternoon! A fun little escape from the cold for a bit!

Water Tower Place - Chicago

The Art Institute is a wonderful place to visit anytime of the year! Chicago’s art museum is home to one of the most impressive collections in the country. Founded in 1879, it’s one of the country’s oldest and largest art museums. How cute is this lion dressed with a holiday wreath?! The Annual Wreathing of the Lions takes place in late November just after Thanksgiving. 2021 marked the 30th anniversary of this iconic event. If you are looking for more holiday museum fun check out the Christmas Around the World display at the Museum of Science and Industry.

Art Institute of Chicago holiday decor

Lincoln Park Zoo, located just north of downtown, puts on a fabulous and colorful holiday light display! Definitely the best zoo light display I have ever seen! Afterwards, warm up with a delicious drink at Mindy’s Hot Chocolate! Best of all, admission is just 5 bucks and free on Mondays.

Lincoln Park Zoo Lights

I like to stop at Hard Rock Cafe after exploring the holiday attractions downtown. The food is consistently great, the atmosphere great, and the holiday decor very festive. Do treat yourself to the Twisted Mac and Cheese and a few delicious appetizers!

Hard Rock Cafe Chicago

Where to find these holiday hotspots

Chicago Christmas Tree and Christkindlmarket
Daley Plaza
50 W Washington St
Chicago, IL 60602

McCormick Tribune Ice Rink (Millennium Park)
55 N Michigan Ave
Chicago, IL 60602

Macy’s Holiday window displays
111 N State St
Chicago, IL 60602

Hard Rock Cafe
63 W Ontario St
Chicago, IL 60654

822 N Michigan Ave
Chicago, IL 60611

Water Tower Place
835 N Michigan Ave
Chicago, IL 60611

The Art Institute of Chicago
111 South Michigan Avenue
Chicago, Illinois, 60603

Museum of Science and Industry 
5700 S Lake Shore Dr
Chicago, IL 60637

Lincoln Park Zoo
2001 N Clark St
Chicago, IL 60614

Mindy’s Hot Chocolate
1747 N Damen Ave
Chicago, IL 60647

Most of these places are within walking distance. Check out the public transportation link below for directions on taking the train to Lincoln Park Zoo any other areas throughout the city.

The “L” Public Transportation in Chicago