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Hi, we're Georgina and Nathan, college friends turned travel partners. We're coffee and animal-loving adventure enthusiasts here to share our favorite travel tips with you! Our goal is to inspire others to get out and explore this wild planet by camping, hiking, or wandering around a fun new city!

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  • Georgina D'Angelo

13 Fun Things to do in Chicago in December

Fun Festive Activities in Chicago for Everyone to Enjoy

Things to do in Chicago in December - Alpacka My Bags

Are you looking for a festive holiday destination to celebrate this year? Then Chicago is the place for you! They go ALL out for the holidays, making it a great place to enjoy the season with lights, hot cocoa galore, Santas, and more.

This city is a great place to visit in winter; there are so many things to do in Chicago in December! It’s festive and vibrant, but also beautiful when it’s covered in a blanket of snow. Chicago is designed to be a fun place no matter the weather, so even if it’s freezing out, there is so much to do and experience.

Read Also: What to Wear in Chicago Winter

If you’ve never been to Chicago, but are planning to go for the holidays, you’ll definitely want to check out some significant attractions as well, such as:

Things to do in Chicago in December

1. Christkindl Market

Breaking news! You don’t have to travel all the way to Europe to enjoy an authentic Christmas market! Chicago is home to Christkindl Market; with multiple locations, you can enjoy the holiday decorations, and different vendors, go shopping and sip on mulled wine to complete the experience!

2. Ice Skating at Maggie Daley Park

There are multiple locations to enjoy a round of ice skating in Chicago, but our favorite is Maggie Daley Park! With a unique “ribbon” shaped rink, it feels like you are ice skating on a frozen river through a beautiful winter wonderland!

ice skating maggie daely park chicago in december

3. Sip on Hot Chocolate at BomboBar

Known for their extravagant s’mores hot chocolate in winter, stop by BomboBar for a truly unique experience. Be prepared to wait though, as it is very popular. I highly suggest going earlier in the day, rather than waiting for the evening. One of their hot chocolates makes for the perfect treat to stay warm while adventuring around the city.

things to do in chicago in december

4. Macy’s Windows

If you enjoy Christmas lights and fun decorations, you have to stop by Macy’s in downtown Chicago! The windows all display their own holiday scene with extravagant decorations, music, and more. This is really fun for kids, but even adults will love it!

things to do in chicago in december

5. Giant Tree in Millennium Park

Home of the giant Christmas Tree, Millennium Park is another fun place to go to. With a 55-foot tree, completely decorated with lights, this is a Christmas sight to see! Even if you don’t celebrate the holiday, this tree will put you in a cheery, festive mood!

things to do in chicago in december

6. Afternoon Tea at The Drake

For a truly magical dining experience, make a reservation at The Drake hotel for an afternoon holiday tea. Suit up in your holiday dress attire and enjoy an array of delicious pastries, teas, sandwiches, and more. This afternoon tea is a fun, yummy way to enjoy the holidays. If you’ve never been to one before, it’s such a lovely experience!

holiday activities in chicago

7. Magnificent Mile

You can’t visit Chicago without walking down the Magnificent Mile, or "Mag Mile" on Michigan Avenue. With shops upon shops and lights all down the street, this is a great place to go window shopping, or maybe even find a gift or two! There is a store for everyone, from Disney to Anthropologie, and more!

things to do in chicago in december

8. Holiday Bars

There are some killer pop-up holiday bars in Chicago! If you enjoy a good cocktail, head to Wrigleyville, and walk around the Wrigley Field area. There are several in this area, you will not miss them. A few of our favorites are Christmas Club Pop-Up Bar and Santa Baby Bar. Remember these will be very busy and are more for the experience.

things to do in chicago in december

9. Music Box Theater

Go for a calmer holiday activity in Chicago and head to the Music Box Theater! This elegant 1920s theater is a wonderful place to visit any time of year, but visit in December and you’ll be able to catch a holiday movie classic or two!

music box theater chicago

10. Holiday Train

In true Chicago style, use the CTA and wait for the fully decorated holiday train to pass through the station. If you’ve never seen a fully decked-out holiday train, then you need to see this at least once! It’s fun for everybody, and you’ll most likely catch Santa waving at you! Check the holiday train schedule here.

cta holiday train chicago

11. The Chicago Roastery

While we prefer avoiding chains and rather supporting small, local businesses, the Chicago Roastery - Starbucks Reserve is honestly a fun experience. With five floors, you can find much more than your typical Starbucks coffee here. They also offer a full food menu, cocktails, coffee tastings, and more. Plus, the lights and decorations are so fun to admire here!

things to do in chicago in december

12. MSI Trees Around the World

If you only have time for one museum, make sure you visit the Museum of Science and Industry (MSI). They have the "Christmas Around the World and Holidays of Light" exhibit which showcases more than 50 trees decorated to highlight different countries and cultures around the world!

things to do in chicago in december - alpacka my bags

13. Lincoln Park Zoo Lights

There's nothing quite like walking around a zoo at night while it's decorated in intricate Christmas lights. Experience this fun time at Lincoln Park Zoo throughout December! Admission is free on Mondays and $5 the rest of the week (at time of post). Fun for the family or for the adults!

lincoln park zoo christmas lights chicago

While there is so much more to experience here, these are all necessary things to do in Chicago in December! You’ll be able to find Santas to take photos with, carols to sing along to, and tons of goodies to buy. Chicago is also home to a killer dining scene, so make sure you eat plenty while in town.

Read Also: 15 Fun Restaurants in Chicago

With lights and decorations and music all around, Chicago truly is the ultimate winter destination! And who knew you could find such a great European Christmas Market outside of Europe! Where will you be stopping in Chicago? Have you been during another time of year before or is this your first time?

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We're Georgina and Nathan, two adventure enthusiasts and creators of Alpacka My Bags. We're here for all of your travel and adventure planning needs! 


We've been exploring this insane planet that we call home together for over 3 years now. After college, we knew the "traditional career path" was not for us, and honestly the "traditional life path", in general, just wasn't for us.


We needed to travel and explore what this world has to offer, it sounds cliché but you do only live once. So we made going on adventures a priority, and soon realized that we wanted to share them with others so they can enjoy them too! 

Our passion is spreading the travel bug and showing others that travel is attainable and so worth it. From itineraries to camping tips to packing lists, Alpacka My Bags has you covered!

Join us, and often our dog, JoJo, as we find exciting adventures and travel recommendations for you! If you've been bit by the travel bug just as we have, we hope you find our tips useful for any and all of your future travels.

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