My Chicago Holiday Bucket List

I can hardly contain my excitement about spending the holiday season in Chicago! Big cities always go all out for the holidays with decorations and festive cheer, and I’m thrilled to start some new Christmas traditions with the kids. I’ve put together a Chicago holiday bucket list with activities I can’t wait to experience during the 2025 holiday season. There’s so much to see and do in Chicago this time of year, but I’ve narrowed it down to a few choice activities I don’t want to miss.

Visit the Christkindlmarket.

Let me set the scene. You’re wandering through a storybook winter village, a steaming mug of glühwein warming your gloved hands. Twinkling lights drape over the wooden booths, casting a cozy glow as you browse handmade treasures and festive crafts. It’s magical! We visited once a couple of years ago when we were in Chicago, and I can’t wait to go back. There are three locations: downtown Chicago, Wrigleyville, and Aurora in the western suburbs. I’d love to start a family tradition of picking out a special ornament from the holiday market each year.

See the Zoolights at Lincoln Park.

This is a beloved Chicago holiday tradition, and one I absolutely don’t want to miss! The Lincoln Park Zoo is transformed into a winter wonderland, with over three million sparkling lights illuminating the paths. You can wander through the displays while sipping hot chocolate. Monday nights are free, but keep in mind that tickets are still required.

Ride the CTA holiday train.

One of the CTA trains gets decked out for the holidays and makes it’s way around the Chicagoland area. Some nights Santa is on board, too! Check out the schedule here to check out when it will be in your area.

See A Christmas Carol at the Goodman Theater.

Seeing A Christmas Carol has been a cherished holiday tradition of mine for nearly twenty years. This year will be extra special, as it’s the first time the kids will be joining us. I’m so excited to share this magical experience with them and start a new family tradition together.

Ice Skate at the Maggie Daley Park Skating Ribbon.

A quintessential Chicago holiday activity—ice skating! It has been years since I last stepped onto an ice rink, but when in Rome. Tickets to the rink are free, though there is a cost to rent skates, with prices varying by date. Another option is the Millennium Park Ice Rink, located near Cloud Gate (also known as The Bean!).

See the Home Alone house.

A lifelong dream of mine! Just kidding (but not really). The iconic Home Alone house, where the exterior shots were filmed (most of the indoor scenes were shot on a sound stage built inside a school gymnasium in Chicago), is a must-see. While we’re at it, we might as well do the full Home Alone Chicago tour!

Eat at a festive restaurant.

We may be a little late to get a reservation at some of the more popular spots, but I know there are plenty of restaurants in Chicago that get decked out for the holidays. From what I’ve heard, Butch McGuire’s, Chief O’ Neill’s, and The Walnut Room are top choices but no longer have reservations available (noted for next year!) I’ll be doing some research for other festive options!

See the Light Of Christmas Drive Thru Display.

There’s something magical about staying snuggled up in the car, watching a display of Christmas lights through your window with a to-go mug of hot chocolate in hand. We used to visit a similar lights display in Kansas City, and it was one of my favorite holiday activities. This one in Chicago takes place at Guaranteed Rate Field, home of the Chicago White Sox. Pro tip: if there’s a line, queue up a holiday movie to watch in the car while you wait.

If you’re from Chicago and have any recommendations or holiday must-sees, I’d love for you to leave a comment on this post. Happy holidays!