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Chicago Holiday Season Bucket List - A Guide to Chicago Christmas Events!

This is my first Christmas living in the city, and I am seriously loving it! The city is so beautiful this time of year (and thankfully not too cold - yet!) Everything is so festive and beautiful, and there is an endless list of ways to get into the holiday spirit! I'm overwhelmed by how many evens I want to attend, trying to cram everything in before I head down to Naples to spend the holidays with my family and escape the chill. 

The holiday activities have also been a great way to explore Chicago more and resist the urge to head straight home from work and curl up on the couch...although I'm still doing that plenty, trust me! For anyone else who lives in the city or visits this time of year - which I highly recommend - I have spared you the headache and compiled a list of all of the amazing ways to spread Christmas cheer Chicago-style. Fingers crossed I can accomplish all or most of the items on this list!


1. Christkindl Market in Daley Plaza - This Traditional German Christmas Market is probably my favorite thing I have seen so far this holiday season. A huge open market of traditional German foods and drinks, musicians and singers, sweet Christmas treats from around the world, and so much more. My favorite has been the indescribable hot chocolate and the fresh ginger bread!

2. Zoo Lights at Lincoln Park Zoo - This was the first thing I heard about when the holiday season approached, and I can definitely understand why! Visit the animals, musical light shows, ice carving, ice skating, and tons of activities for little kids too! You can also visit during Brew Lights, with dozens of draft beers and pale ale served among the 2 million holiday lights. (I've been to this one three times already...no shame!)

3. Ice Skating at Millennium Park - Having visited Chicago many years before I moved here, ice skating at Millennium park is not new to me but it will always be one of my must-do activities during the winter. It's so incredible to see the entire city and all of its lights surrounding you, with ice skaters and music everywhere and the cafe serving hot chocolate and treats. My favorite thing to do is go out to dinner, head to the ice rink, then walk down Michigan Avenue to look at all of the incredible Christmas displays in the shops.

4. See one of the Chicago-Famous Holiday Shows - Being from Louisville, we always went to Christmas plays and shows but you can't beat the big-time shows in cities like Chicago. The Nutcracker and A Christmas Carol have been running for over 30 years, and they've stuck around for a reason! I can't wait to try this new experience out in my new home next week!

5. Catch the CTA Holiday Train - I've been chasing this around for the last week so far and still haven't gotten a ride, but I've seen it on SnapChat and even a glimpse from the street when I was walking to dinner one night...major jealousy. One train on the "L" in the city is decked out in Christmas lights, displays, music, and elves handing out candy and Christmas Cheer for the entire month. Determined to catch it soon!

6. TBOX - The Twelve Bars of Christmas 12 Hour Bar Crawl...I think the name kinda says it all with this one. People have been asking me if I've bought my ticket since before the Halloween bar crawl in Wrigleyville! (And people get upset when people play Christmas carols before Thanksgiving...sheesh). An all day event in Wrigleyville that has been described to me in a hundred different ways, but it seems to be the holiday event of the season. I'll definitely let you know how it goes after this weekend!

Does anyone else have any helpful tips or holiday must-see events in Chicago? Please share with a rookie Chicagoan, I'm loving all of the exploring!

PS - Suddenly for the first time, I'm noticing the insane amount of Christmas movies that take place in Chicago/Chicago suburbs...Can't be a coincidence! You just can't beat Christmas in Chicago!

Happy Holidays!

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2 comments

  1. You are right, Home Alone takes place in Illinois near Chicago and its a classic! I'd love to visit Chicago this time of year!

    Laura | Laura Aime Vous

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    1. I know, my friend's uncle lives right near there and he said he stops by the house all the time. It's also the same town they used the high school for Ferris Bueller from! What a famous little suburb!

      xo Olivia

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