10 Things to do in Chicago for the Holidays

You know that song…”There’s no place like home for the holidays“?

Chicago at Christmas time is a city full of lights and wreaths.
Well to us, that lyric definitely rings true. We absolutely love being in Chicago around Christmastime. The city is just such a magical place filled with twinkling lights, crisp air, and holiday tradition.Twinkling Christmas trees and decorations are all around Chicago during the Holiday season.

To celebrate our love of Chicago and the holiday season, we decided to combine them both into a post outlining our favorite things to do around here this time of the year.The Macy's Christmas windows are a great holiday destination in Chicago.

So if you’re from Chicago or plan to visit Chicago someday soon, we hope this list helps guide your activities when in our home sweet home. Here are 10 things to do in Chicago for the holidays.

1. Ice Skate at Millenium ParkThe Bean in Chicago is beautiful in the Winter time.

Ice skating in millenium park is a must-do in the winter. Right underneath “The Bean” you’ll find a small ice skating rink in Millenium Park. It’s a cute little spot filled with families, couples, and anyone looking to enjoy this holiday activity. We suggest going at an off-time (i.e. not a weekend), so you don’t have to wait in long lines to skate. If you have your own skates, bring them! You’ll skip the rental line and be able to get out on the ice much faster. Check out the City of Chicago website for more information.

2. Ride the Holiday Train

Each year during the holiday season, the CTA has a holiday train that runs around the city.  The train is covered in lights, the inside of each train car is decorated from top to bottom, and they blast Christmas music. It’s amazing and makes commuting around town waaay better. The holiday train runs a certain schedule (you can find this year’s here), and you can try your best to find it on that particular day. When Finn & I moved back to Chicago a couple years ago, we made it our mission to find the holiday train one random Saturday. After running around to different train stops, we finally found it! And here’s my big grin from that day…Take the city holiday train to get in the Christmas spirit.

It’s so funny because last year I was heading home from work on a random day, and to my surprise my train home was the holiday train! So sometimes it will show up when you least expect it to brighten your boring routine.

3. Visit Christkindlmarket Chicago

This is a German market in Chicago’s loop. Every year they set up a little village of food, drink, and shopping vendors and it has become one of the most popular winter attractions in the city. You can walk around with a beer stein and get some of your holiday shopping done! But (like #1) it can get suuuuper crowded. So try to visit on an off-night to bypass the crowds. You can find more info here.

4. Check out the ZooLights

The Christmas lights at the Lincoln Park Zoo light up the cold winter night.

Image via Lincoln Park Zoo

This is such an amazing activity, especially because it is F-R-E-E. Yep, the Lincoln Park Zoo is free all year round, and it remains that way even during the holiday season. The entire zoo is illuminated in lights and they also have fun activities like ice carving and carousel rides. A family-friendly favorite! You can find more info here.

5. Shop on Michigan Avenue & State Street

Doing all your Christmas shopping at Chicago's magnificent mile is a a fun holiday activity. Sure we love to online shop like no other, but there’s just something about shopping on the iconic Magnificent Mile for your holiday gifts. Even if you just window shop the designer stores while sipping on your hot cocoa, it’s still a fun place to be around the holidays.

6. See the Joffrey Ballet’s The Nutcracker

When I (Casey) was a little girl, every year my mom would take me and a friend downtown to see The Nutcracker. We’d get all dressed up, have a nice ladies lunch, and then hit a matinee. I looked forward to it every.single.year. I don’t get to a show every year these days, but I look forward to the day when I can bring my own daughter to this gorgeous ballet.Joffrey Ballet's, The Nutcracker is a must see in the city.

7. Have a beer pint at Butch McGuire’s

For the last 45 years, this Irish pub has been decorated from top to bottom with Christmas decorations each holiday season. This iconic spot even has a double-decker model train that zooms around the entire restaurant. Definitely worth a visit if you’re in Chicago during the holiday season.

8. Check out the windows and iconic tree at Macy’s (previously Marshall Field’s)

The Macy's Christmas windows and tree and Chicago holiday staples.
For the holidays, the windows along Macy’s on State Street are dressed up for the holidays. If you walk window by window you can follow the “storyline” and enjoy a staple Chicago Christmas tradition. When you’re too cold to stay outside a minute longer, hop inside the historic 9-story Macy’s (!!) to enjoy dinner under the iconic (and HUGE!) Christmas tree in the Walnut Room. You may want to go early or stop in to put your name on the list for the evening, because this Chicago staple fills up quickly around the holidays.The Christmas tree in Macy's Walnut Room is a Chicago favorite. Grab a coffee mug souvenir at Macy's Walnut Room in Chicago.

9. Watch “It’s a Wonderful Life” at the Music Box Theatre

I don’t know about you guys but I (Bridget), along with my family, are huge fans of the Christmas classic “It’s a Wonderful Life”.  If you heart George Bailey and Bedford Falls as much as we do then you don’t want to miss seeing this iconic movie on the big screen! Throughout the month of December, The Music Box Theatre, an adorable old-fashioned movie theatre, plays this movie. And to make the experience even better, a dressed-up Santa Claus comes out during the previews and hosts a Christmas carol sing along. Oh and if you do decide to go to this one-of-a-kind event, don’t forget to bring some bells. You fellow fans know what happens every time a bell rings…. 😉

10. Take a Carriage RideExploring Chicago's festive decor is a magical way to enjoy Christmas time.
If you’re looking for a magical way to explore the busy streets of Chicago, a Christmas carriage ride may be right up your alley. You can hop on a private carriage ride with your honey (or family!)  right around the old water tower on Michigan Avenue. Pick up some hot chocolate on the way, bundle up, and enjoy the gorgeous lights and holiday hustle and bustle up and down the Mag Mile.

Chicago's silver Bean gleams in the winter light. Looking for more Chicago posts? Check out this list of Chicago activities and this one featuring our favorite photos spots.


The Year of Casey

Hey there!

I’m Casey Finn, the voice behind The DIY Playbook. I’m a Chicago gal teaching you how to design, DIY, and maintain your home…by yourself! Learn more about me right here.

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