I have to say….

Chicago might just be one of my favorite places to spend a holiday weekend. I recently went to visit the city right before the Thanksgiving holiday, and I’ll admit, I was a bit nervous. As a California girl, I rarely encounter weather below 40 degrees. And so, it didn’t help when everyone’s first reaction to hearing about my winter trip is, “but Chicago is so cold!!”

Challenge accepted.

the iconic Chicago theater

And I’m happy to say, it was one of the most magical trips I’ve been on yet. Why? Well, they take the holidays there seriously. From the most insane holiday pop-up bar to a lights parade of a million people, Chicago is THE place to go to get into the holiday spirit. I came back to San Francisco a changed woman, imbued with holiday spirit. I haven’t had a Christmas tree in years… and well after Chicago, that was one of the first things I did. So you know, that was a life-changing trip! Read on to see what are the must-do holiday activities for when you visit!

1. The Annual Chicago Christmas Tree Lighting Ceremony

It was funny because I had just gone to a tree lighting ceremony in Sonoma a week before, and it was a WORLD of difference. In Sonoma, I missed the actual lighting of the tree because it was a palm tree and I couldn’t see it, ha! In Chicago, it is an epic Christmas tree. What you expect from a Christmas tree! All covered in gorgeous lights, decor, and festive holiday spirit. And it isn’t just a tree lighting, we saw some amazing live performances where we were able to discover new artists.

2. Ride the Chicago Holiday Train

I wish I got better pictures but riding the Chicago holiday train was one of the best experiences I had in Chicago!! This is a special train that is decorated completely in Christmas festivities, including neon lighting and new upholstery. The best part? The AMAZING smell!! It smelled like cinnamon… And for anyone who has been on public transportation, you KNOW that that is a Christmas miracle. And of course, Santa rides along with the train, and his elves are all the train conductors!

3. BMO Magnificent Mile Lights Festival Parade

And of course, you can’t miss the iconic Magnificent Mile Lights Parade. It is an epic parade, over 1 million people attend every year!! The floats are so fun— from a Disney one to a sports one with all the mascots, there is no end to the entertainment on this parade. We were lucky enough to BE in the parade, waving just like a pageant queen :P.

Bonus! Stroll Through the Gold Coast Historic Neighborhood

a house in the gold coast historic district

If you want to see a plethora of festive holiday homes, the Gold Coast is the place to go. This historic neighborhood goes all out, with huge installations of reindeer, Santa, and even nutcrackers! I also heard it’s a must-see during Halloween. Take a stroll before heading to brunch at the 3 Arts Club.

an amazing group of new friends!

Where’s your favorite spot to celebrate the holidays? I’d love to know— tell us in the comments! 

Cultural Chromatics has teamed up with Choose Chicago, the Chicago tourism board, for this post. However, all opinions are our own, (and always will be). Thanks for supporting content that keeps the lights on here at Cultural Chromatics. 

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