The Best Holiday Activities in Chicago
Disclaimer: We are not paid to promote any restaurant, hotel, activity, product, or attraction. All opinions are subjective and based on our personal experience. Your experience may be different.
Update: If you are looking for the best spots to see the grand Christmas tree and the famous Macy’s window displays, be sure to visit my Christmas in Chicago guide for further details.
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.
I love the winter season in Chicago. Even though most tourists prefer the summer, I love the festive holiday events, the high likelihood of snow, the ice rinks, and the many cozy local restaurants that populate the metro. This is my favorite time of the year to visit the city, especially Millenium park to ice skate.
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
- browsing for unique ornaments at Christkindlmarket
- holiday shopping on Michigan Ave.
- seeing the iconic Macy’s holiday window displays
- heading over to Lincoln Park ZooLights event
- ice skating at Millennium Park
The history of the Chicago Christmas tree
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. Being a Chicago native, I headed downtown to see this tree almost every year as a child. Anytime I am back in the city around the holidays (which is rare), I try to get downtown to take in the holiday cheer.
Read more about the history of the Chicago Christmas tree
Update: I finally planned a winter visit back home for Thanksgiving and I was able to see the new tree at Millennium. It’s so gorgeous. What do you think of the new tree in comparison to my old pic from 2012?
Holiday Bucket List
Check out my guide to the best activities and events to look forward to this holiday season.
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 big city rinks I’ve ever seen offer free admission), 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).
Update: There are now a number of festive ice rinks downtown including a unique ribbon shaped rink at Maggie Daley Park which I have been dying to skate on for a number of years now. Here is a pic from my 2025 visit. The rink looks so gorgeous at night!
Seeing the Macy’s on State Street holiday window displays is always a must-do during the holiday season. Seeing these windows was a big thing each holiday season when I was a kid. We would look at the gorgeous tree and then make our way over to state street to see the windows. Then, we would browse around the gigantic Marshall Fields department store and never buy anything, but still have a blast looking.
The spirited windows are conveniently located just a short walk from Christkindlmarket. 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, nostalgic fans of the beloved Marshall Fields holiday window tradition continue to make the trek downtown for this long running city tradition.
Update: Here is a picture of one of the window scenes from the 2025 display. It was actually a fun throwback to the past display. I was so shocked when I arrived downtown and found no crowds! In the old days, we would be 3 rows deep trying to see over the heads of the throngs of crowds lining up. It was so crazy seeing it so empty. Christkindlmarket on the other hand was super busy.
Also, if you feel like shelling out a few bucks, you can reserve seats for dinner at The 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: Wow after almost 15 years of wanting to do so, I finally scored reservations to The Walnut Room. It was an incredible dining experience just like I imagined. Dining on delicious food while taking in views of The Great Tree was such a magical holiday experience. The Franco Mint Cheesecake is so amazing. And I just loved the Marshall Fields themed tree for 2025. What a fitting year (my first time back in the city for the holidays in like 15 years) and the tree is a nostalgic throwback to the past. Just perfect!
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 & Ghirardelli shops as they have cute decor and tons of cute little trinkets and gifts. Update: Hershey’s is now closed. Check out Eater’s guide to the best cocoa in the city for an alternative.
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!
The Art Institute is a wonderful place to visit anytime of the year. The Windy City’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.
Lincoln Park Zoo, located just north of downtown, puts on a fabulous and colorful holiday light display! I have been to a lot of festive holiday zoo events, and I still like this one best. Afterwards, warm up with a delicious drink at Mindy’s Hot Chocolate! Best of all, admission is just 5 bucks and free on Mondays.
Update: As of 2025, tickets are now $7-12 with most mondays being free. Not a bad deal considering most zoos charge $20-30.
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!
Update: The Hard Rock is now closed. What a shame – I love this place! Fortunately, there are endless dining choices in this city. If you are looking for something fancy, I recommend The Rosebud on Rush (you will find no better Italian restaurant in the city). For casual fare, you can’t beat Giordano’s deep dish and Lou Malnati’s (a long running Chicago favorite serving the best veggie lasagna!).
Where to find these holiday hotspots
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
Hershey’s
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.
