A collection of the best Chicago holiday activities, from a family that has done them all! We stayed in Chicago for all of winter break, taking advantage of Chicago's many Christmas events and activities.
I am writing this with the goal of helping you to choose the holiday events and activities that you will enjoy the most.
You can read even more about Chicago Christmas Activities here.
Best Chicago Holiday Activities
Best Holiday Lights Event: Chicago Botanic
We were blown away with the light displays at Chicago Botanic's Lightscape. It felt immersive and truly magical. I took my parents, husband, and five-year-old daughter, and we all had a blast. This is an extremely popular event that does sell out, so book tickets in advance. Don't be scared off by cold weather. There are plenty of tents throughout the 1.3 mile trail where you can warm up.
Morton Arboretum
Illumination at the Morton Arboretum transforms vast landscapes with lights, decorations, and music. I prefer the Lightscape at Chicago Botanic, but I have friends who prefer this. Illumination did feel more nature-focused. We happened to go while it was snowing, and it added an element of magic to the experience.
ZooLights
ZooLights is fun! If you live in Chicago, this is the most easily accessible light event. It's also more affordable and has more activities for children.
Note: all these of the light experiences offer adult-only nights.
Best Theatre Experiences: The Nutcracker and Beatrix Potter Tea Party
The Joffrey Ballet's Nutcracker is simply stunning. I loved how the Chicago World's Fair was incorporated into the story and the sets were spectacular. I am already excited to go back next year. I took my five-year-old, and she got a little antsy here and there, but overall, she loved it. I wouldn't bring a child younger than age 5.
There is one very important thing to know about seeing The Nutcracker at the Lyric Opera. If you leave your seat to use the restroom during the show, you will not be allowed to return to your seat until intermission. Yes, this strict rule applies to children as well.
The Beatrix Potter Tea Party is a darling play for young children at the Chicago Children's Theatre. It tells four classic Beatrix Potter stories, and the runtime is under an hour. It's great for children ages 2-7.
Elf
We need to stop the trend of turning 90-minute movies into 2-hour-and-30-minute Broadway musicals. Elf had too much filler. It was fun, but my five-year-old got a little restless during some scenes. As an avid theater-goer, I'd give this musical a 4/10 review.
'Twas the Night Before
Compared to Elf, this Cirque du Soleil show is much faster-paced and better for young children.
Best Fun-for-the-Whole-Family Event: Christkindlmarket and Winterland
Skip the overcrowded downtown Daley Plaza Christkindlmarket location where the wait to get in can be over an hour long. Instead, visit the location at Gallagher Way, the park beside Wrigley Field. This Christkindlmarket is far less crowded and offers the same experience - and the same mulled wine in decorative mugs.
Besides being less crowded, this location has Winterland activities, including an ice skating rink and a train ride for children.
Best Activity for Children: Winter Wonderfest at Navy Pier
This annual event at Navy Pier's festival hall includes ice skating, carnival rides, bounce houses, inflatable slides, and a few food vendors. Priced at $40, the tickets include ice skating, skate rental, and unlimited carnival rides. The ticket even includes a ride on the Centennial Wheel, which usually costs $20+. The value for money is incredible.
I brought my five-year-old, and we spent four hours here. She was able to go skating and do most of the rides (most had height requirements). The ideal age range for this event is children between the ages of five and ten. There were bounce houses and a few activities for toddlers.
The Event to Skip: Passport to Santa
This pop-up experience was hosted in several cities across the country. It came to Chicago's Pioneer Court, where it was a family-friendly event by day and a naughty burlesque club at night. Influencers were paid to promote the event, and after seeing their positive reviews, I bought tickets. The tickets were $40 per person, and it felt rushed, crowded, and cheap. Children were given a very small toy (you could pay an additional $15 for a stuffed animal), got to decorate a cookie, did some quick activities, made an ornament, and met Santa. Adults receive nothing in exchange for the $40 admission - except the chance to chaperone their child and the opportunity to purchase a cocktail for $20-$25 at the end of the event. The "Rockette style entertainment" was a clown who briefly spun plates before letting children on stage to throw scarves around. Skip this and take your $40 to Navy Pier and spend hours enjoying the activities there.
