Ultimate Guide to Chicago’s Popular Christmas Experiences

It may be a bit chilly, but I firmly believe that Chicago is one of the best cities to celebrate Christmas. Why? Because there are so many beautiful and unique family friendly experiences that truly capture the spirit of the holidays. The only downside is that your family isn’t the only one who wants to dine with Santa at the Walnut Room nor drink glugg at the Christkindle Market. But if you follow some of my Ultimate Guide to Chicago’s Popular Christmas Experiences, I promise that you will have a very merry time (and maybe save a few bucks, too!):


Photos with Santa

Thankfully you can now make reservations with Santa so you don’t have to wait in a mile long line, but if you visit the authentic and Jolly Old Nick at Northbrook Court, waiting isn’t an issue. 900 North Michigan is another popular spot, or you can visit the Santa suite at the Swissotel…which is totally FREE! Be sure to visit during the weekday in the early afternoon…it is a breeze and just plain wonderful experience!

Morton Arboretum

Illumination is one of the most beautiful ways to celebrate the season of lights…just be sure to bundle up because you have to walk the trail instead of driving it! Buy your tickets early and try to avoid visiting when schools are on winter break because it can get very crowded. Oh, and to save some money check out the Groupon Deal and this buy one get one coupon from Com Ed.

Christkindle Market

Hard to spell but oh so much delicious fun. And if you manage to visit on a day when it snows? It feels truly magical. What’s not so magical? The crowds…because there are TONS of them! If you are looking to avoid some of the chaos, be sure to visit during the late afternoon (3-4:30 is a great time frame) during the week. You can also try to visit right when it opens on weekends, but it gets crowded VERY quickly. You have been warned. Oh, and don’t forget to enjoy your boot of glugg and baby carrier (leave the stroller at home!) This year there are also locations in Naperville and the Park at Wrigley, and I must tell you that the Park at Wrigley’s Winterland is PERFECTION! There is ice skating, photos with Santa, and the same delicious food and drink and handmade European crafts as the original market downtown but it is so less crowded and a much more enjoyable, family friendly experience.

CTA Holiday Train

I’ve heard from so many readers that my tips ensured them a festive ride last weekend. Check out my article about the Holiday Train and Bus so your family doesn’t miss out!

Chicago Botanic Garden Wonderland Express

Calling all train lovers…don’t miss out on the CBG’s magical holiday experience! Although the exhibit is located indoors, there is an outdoor walk to arrive there so be sure to bundle up and feel free to bring a stroller or wagon since there is ample stroller parking outside of the exhibit. Be prepared for festive fun made out of all natural products, including an indoor snowfall at the beautiful Wonderland Express.  And scoop up some discounted tickets to save on parking and admission through Groupon or this buy one get one coupon from Com Ed.

Walnut Room

There is nothing like the tradition of eating a meal under the beautiful Christmas tree at the Walnut Room. Want in on the fun without waiting in line for hours? Here is my insider tip: Arrive at 8:30 a.m. before it opens so even if you do have to wait, it is only for a very short amount of time. And don’t forget to visit Santa on your way out!

Zoo Lights

Both the Lincoln Park Zoo and Brookfield Zoo put up impressive light shows, but the Brookfield Zoo parking situation can be quite a headache. Heck, the Lincoln Park Zoo one can be a hot mess, too. So my tip is pretty straight forward: Arrive slightly before it gets dark out to snag a spot and check out the animals while you wait for the lights to come on. Easy peasy.


And while it might not *technically* be Christmas themed, be sure to check out the Ice Castles exhibit that is in Lake Geneva this season!

What is your favorite Chicago Christmas experience?

Looking for the best Christmas light displays, unique meals with Santa, or other Holiday Fun in Chicago?

Happy Holidays!
Don’t miss a post…follow me on Blog Lovin’.


  1. Alli Smith says

    I’ve never been to Chicago during the Christmas season. I would love to visit and see all the lights and visit the Botanical Gardens. It would be so much fun.

  2. Pam Wattenbarger says

    I have always wanted to visit the Christkindle Market. I see photos of it every year from my friends who live in and around Chicago.

  3. Angelic Sinova says

    I might be bias because I’ve lived here all my life but Chicago IS the best city during the holidays (and I’ve experienced NYC, DC and LA during this time of year and nothing compares to Chicago!). I LOVE going to ZooLights each year! All the light displays are so gorgeous!

    • Amanda says

      That’s why I hate to travel during Christmas…there are so many fun and beautiful things to do and see. Now in January, then I’ve got to get away from the frozen tundra!

    • Amanda says

      It is a really fun and festive way to get from place to place…and the best part is when you are totally surprised by it because it replaces your typical train/bus!

  4. Jeanine says

    Oh how fun this would be to visit! I’ve never been to Chicago so this is the first I’ve heard of this an it sounds great!

  5. michele dickerson says

    I’ve never been to Chicago but I bet it’s so pretty around the holidays. This event looks like a blast.

  6. Christina Aliperti says

    This would be a great family trip. We have never been to Chicago and it seem the holiday season is perfect to visit.

    • Amanda says

      It would be impossible to do all of these things in one day so I recommend you plan a visit to these great spots all throughout the holiday season.

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.