7 Must-Do Holiday Activities In and Around Chicago

Posted on December 13, 2017

Believe it or not there are holiday activities that don’t include watching movies on the Hallmark channel, especially when you’re in Chicago. In the winter, the city encapsulates the perfect holiday scenes depicted in the movies you’ve seen every year since you were 5 years old. Cold, snowy and full of bright lights and decorations that bring out the kid in everyone.

So why stay indoors when one of the most magical places during the holidays is waiting right outside your door?

If you don’t know all that Chicago has to offer during the holidays, don’t fret. We’ve got you covered. From the must-do’s to the under-the-radar events that are sure to bring joy to you and your family.

1. Ice Skating at Millennium Park

We’ll start with what may be the most popular activity in Chicago during the winter. If you’re a visitor during the holidays, you will undoubtedly hear about or see the ice rink at Millennium Park. It offers a great view of the downtown skyline and is a memorable activity if you’re looking for something to do for a fun family outing. If you’re looking for a more intimate experience on the ice, you can head over to ice rink at the The Peninsula Chicago. While you’re there you can also treat yourself to their famed holiday tea. Even if you’re from Chicago you will most likely attempt to channel your inner Chazz Michael Michaels at least once during the holidays.

Dates: November 17 - March 4
Pricing: Free if you bring your own skates. Skate rentals are available for $12 Monday-Thursday and $14 Friday-Sunday/Holidays.
Address: 201 E. Randolph St. Chicago, IL 60601

2. Christkindlemarket
Another Chicago must-do during the holiday season is taking a stroll through Christkindlemarket in Daley Plaza. This Chicago tradition is for tourists and locals alike. It’s Chicago’s largest open-air Christmas festival and brings German and European culture, including authentic food such as potato pancakes and sausages, traditional drinks, including a wide selection of beer and Glühwein, and specialty gifts like nutcrackers and beer steins. They have recently expanded into Naperville, making it easier for those in the suburbs to join in on the fun. And for those of you in Wrigleyville and surrounding areas, they didn’t forget about you either. Also, don’t worry about the language barrier. You don’t have to speak German in order to enjoy the festival.

Dates: November 17 - December 24
Pricing: Free
Address: 50 W. Washington St. Chicago, IL 60602
                 523 S. Webster St. Naperville, IL 60540
                 3637 N. Clark St. Chicago, IL 60613

3. Zoolights at Lincoln Park Zoo
Falling in between a must-do and under-the-radar, Zoolights is a family-oriented holiday celebration featuring luminous displays and holiday-season activities throughout the zoo grounds. Filled with the ever popular picture with Santa, live ice-sculpture carving, musical light shows and even a polar journey experience, this is a perfect opportunity for the family to experience everything the holiday season has to offer. This celebration also transcends age, with adults possibly enjoying it more than the kids.

Dates: December 8 - January 7
Pricing: Free entry. Tickets for rides start at $3.
Address: 2001 North Clark St. Chicago, IL 60614

4. Chicago Trolley and Double Decker Holiday Lights Tour; CTA Holiday Train
If you’d like to experience the magic of riding on a sleigh being pulled by eight reindeer, this is the closest you can get. Minus the reindeer, but you also have so much more leg room. The Holiday Lights Tour is a great way to catch a couple of the aforementioned events as they make stops at Chirstkindlemarket and Zoolights. As you take this expedition across the city, you’ll have a chance to see all the holiday decorations while enjoying a free cupcake from Sprinkles. If a trolley or double decker isn’t your cup of tea, the CTA has also rolled out its famed Holiday Train onto the tracks. This holiday tradition is unique to Chicago and includes a Santa on a sleigh in the middle of the train.

Dates: November 24 - December 23
Pricing: Adults - $29; Children (5-15) - $18
Address: 875 N. Michigan Ave. Chicago, IL 60611

5. Holiday Shows
None of these theater shows are really under-the-radar when thinking about the holiday season, however, with Hamilton being all the rage, these seem to have been lost in the shuffle. Chicago offers all the classic shows like Goodman Theatre’s “A Christmas Carol,” Joffrey Ballet’s “The Nutcracker” and Broadway Playhouse’s “‘Twas the Night Before Christmas,” which the entire family will enjoy. Trust us, you don’t want to be a Scrooge this season by not taking the family out to a show (if you don’t know who or what a Scrooge is, then we recommend you attend all the shows immediately).

Dates: Most run to the end of December
Pricing: Varies

6. Christmas Bar Pop-ups
The holiday’s are usually a time were you can experience events that come around only once a year. With holiday-themed decor and drinks, such as the “Snowball Old-Fashioned” and “How the Gimlet Stole Christmas,” Brando’s Speakeasy’s Christmas Cocktail Pop-Up is full of holiday spirit (pun intended). Lost Lake will also be hosting a pop-up for the second consecutive year. Whether you want to spend a couple hours away from all the family madness or if you want to make this a family outing, you can’t really go wrong with trying the “Run, Run Rudolph” concoction. 

Dates: November 24 - December 24
Pricing: Free entry. Drink prices vary.
Address: Brandos Speakeasy - 343 S Dearborn St. Chicago, IL 60604
                  Lost Lake - 3154 W. Diversey Ave. Chicago, IL 60647

7. Hot Chocolate Options
If your holiday consists of young children, but you still want to experience a beverage synonymous with the holidays, we’re sure you and your family will enjoy some of the best hot chocolate options around. BomboBar is your prototypical hipster hangout that will instantly make you the coolest parent in town. Their “Hotter Chocolate” is particularly exceptional and comes with funfetti and smores (make sure you renew that gym membership). If you’re looking for a place where you can accompany your hot chocolate with some pastries, Bittersweet Pastry Shop is one place you must try. Its signature hot chocolate is even better when you pair it with an apple muffin or a poached pear and hazelnut tart.

Dates: Open year round
Pricing: Varies
Address: BomboBar - 832 W. Randolph St. Chicago, IL 60607
                  Bittersweet Pastry Shop - 114 W. Belmont Ave. Chicago, IL 60657