Best Christmas Activities in Chicago

Every year my Mom and I take an annual trip to Chicago in December to soak up the Christmas décor of the city. Since we were unable to go this year due to the pandemic, I was able to reminisce about my families past visits.

Below is a list of my must-do activities to do in Chicago during Christmastime.


This is my number one stop! If you only have time for one activity then do this!

The Christkindlmarket is a Christmas market held in Daley Plaza. The market features a number of delicious food and warm drinks to enjoy from brats, hot chocolate, and German pastries. Many annual visitors are familiar with their collectable souvenir mugs.

The market is perfect for unique gifts for hard to buy for friends and family, it’s also the ideal way to get into the Christmas spirit. There are many holiday vendors selling a variety of handmade gifts. Ornaments are by far the most abundant, lining multiple walls of tents and displays.

Ride The Polar Express

The Polar Express attraction Experience leaves from Chicago Union Station, and yes, it is a real train ride.

I went on The Polar Express with my family when I was nineteen, it seems old, but better late than never. The whole experience from start to finish made me feel childish, warm, and fuzzy, like how you feel during the holidays when you’re six or seven years old.

The experience starts when you find where you board the train. Riders are ushered into a blue lit room with floor to ceiling snowflake and holiday décor accompanied with music from “The Polar Express” soundtrack. You’re given your train ticket and not long after you’re ushered into a Christmas decorated train car.

The trip is one hour long and takes riders through iconic scenes of the movie. Naturally, characters from the movie make an appearance, even Santa. I enjoyed the hot chocolate and snacks the most. The hot chocolate number is my favorite part of the movie and being able to live it was definitely a childhood dream come true.

This experience is perfect for families, especially with younger kids. Pajamas are highly encouraged (my family wore matching pj sets and we fit right in).

Christmas Around the World: Museum of Science and Industry

The Christmas Around the World exhibit showcases the cultures of forty different countries through Christmas trees. In the middle of the display stands one four story grand tree that’s worth the trip in and of itself.

Its a gorgeous exhibit to walk around and it’s fun to pick out trees from countries your family is from or guess the country simply by the tree’s décor.

The Museum of Science and Industry is a necessary stop regardless of season, this exhibit is just an incredibly big perk come Christmastime.

Go See a Christmas Show

From play performances to concerts Chicago was a hub of entertainment pre-COVID. In past years my family has attended Christmas concerts since we love Christmas music so much. My favorite concert was the Pentatonix Christmas Tour from 2017. If you’re a fan of acapella I highly recommend you check them out if you aren’t familiar with them already.

Christmas Shop on the the Magnificent Mile

Since my family doesn’t live in a major city like Chicago visiting gives us a chance to get a lot of shopping done. Not only that, but my Mom and I love shopping as a hobby, no holiday gift giving necessary. We make a point to go shopping every time we visit Chicago regardless of the season, and the Magnificent Mile is definitely an epicenter of stores we come back to.

Garretts popcorn always makes a great gift!

Go on a Carriage Ride

If your party decides to go for a carriage ride be sure to bundle up! Luckily in most carriages in winter months they have blankets for people to use.

At night carriage rides are great for seeing the Christmas lights of the city.

Get Hot Chocolate from Ghirardelli Chocolate Co.

Ghirardelli Chocolate Company has the best hot chocolate, especially if you’re like me and love the whip cream, marshmallows, chocolate drizzle, the works.

My family and I usually try to sip on our hot chocolates on our carriage ride.

Go on a Holiday Trolley Tour

If you’re looking to see most of what Chicago has to offer during Christmastime wrapped up into one activity or you simply don’t have a lot of time, then a trolley tour could be right up your alley. Many tours let guests hop off at certain stops and explore the holiday highlights in the city.

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