Chicago’s Best Family Holiday Activities
The Chicagoland area has some wonderful family-oriented activities to help you celebrate the Holidays and have fun together. We have a whole list of activities that we want to do each Holiday Season to take advantage of all of the cool happenings in Chicago. Chicago shines during December and whether you live here or are just visiting – take advantage of the fun.
Here are a few well-known and lesser-known local Holiday favorites that my family loves to do. Many of these have become Holiday Traditions that our kids look forward to every year.
Younger Kids:
- Wonderland Express – Holiday Train Exhibit at Botanical Gardens
- Zoo Lights at Brookfield Zoo
- Winter Wonderland at John Hancock Building – The Christmas tree is beautiful, the train exhibit inside is delightful for kids, and get a free photo with Santa every weekend from 12 – 4 p.m.
- Winter Wonderfest at Navy Pier
- Drive around the neighborhoods and see the lights or see the Winter Wonderland Holiday Light Show at the Cuneo Museum – perfect for little kids who can’t walk far or for those nights when it is absolutely freezing
Kids Aged 6 and up
- Christkindlmarket in Daley Plaza – This is my family’s favorite thing to do every Christmas. We have been 3 times already this year. The hot sausages, German pastries, beautiful ornaments from Germany and the Gluhwein make it a hit for parents and kids.
- Christmas Around the World at the Museum of Science & Industry – While the exhibit is nice and has a lot of great history, definitely check out the Dr. Seuss exhibit this Holiday Season. The Gingerbread Museum in the lobby is AWESOME!
- Christmas Carol at the Goodman Theater or Joffrey Ballet Nutcracker - we alternate these two shows every year. This year we’re going to the Nutcracker Ballet. Joffrey’s version is the BEST. I’ve seen it 6 times. Last year, the kids LOVED the Christmas Carol. The stage and the special effects were incredible.
- Nutcracker Tea at Seasons of Long Grove or Holiday Tea at the Drake Hotel is a special moment for the whole family or a Mom, Daughter and Grandmother event. I met a friend for Holiday Tea at the Drake Hotel this past weekend and the decorations were spectacular. So many adorable little girls in fancy dresses!
- Ice Skating Millenium Park – Rockerfeller Plaza doesn’t have the mighty Bean sculpture behind it, now does it? Friday nights in December there is caroling in front of the Cloudgate sculpture (aka the Bean) at 6 p.m. Haven’t gone yet but I’m sure the photo ops are incredible.
Any Age:
- Carriage ride on Michigan Avenue – Grab yours by the Water Tower
- Tower Brass Holiday Concert at Fourth Presbyterian Church on Michigan Avenue
- Shop windows at Macy’s on State Street, then see the beautiful, decorated Christmas trees at Water Tower Place, 900 North Mall or NorthBridge. There is supposed to be an incredible, 5 story Grinch display in Water Tower Place so check it out.

– We go every year. It’s amazing. This year it is scheduled for Saturday, Dec. 17th at 2:30 p.m. Save us a seat, we’ll see you there.
No matter what you decide to do this year, create some memories and have some Happy Holiday Fun with your family!
What are your favorite things to do in Chicago during the Holiday Season?
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