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8 Ways to Kickoff Christmas in Chicago

For the first 29 years of my life, I celebrated the holidays in Hummelstown, Pennsylvania. While we’re not a religious family we have deep-rooted holiday traditions that I cherish more than I could ever put into words. There will never be a day I forget what our homemade popsicle stick star looks like, the taste of filling balls or the words to Raffi “Old Toy Trains”. Leaving home and traveling nearly full time meant I would be missing out on many of these moments. It is something I still struggle with whenever the holidays roll around. In return, I’ve gained the freedom to create my own traditions. Travel has, of course, become a huge part of those traditions. Feeling so grateful that each year means new light displays, new parades,  new holiday meals.

This year we had the opportunity to kick off Christmas in Chicago with the amazing folks at Enjoy Illinois. We spent a few days absolutely buzzing around the city devouring the best deep dish pizza in Chicago (Gino’s East), listening to Blue Man Group and shopping until our hearts were content. Believe it or not, we even got to be part of the ultimate Christmas in Chicago kick off, the Magnificent Mile Lights Festival Parade! Talk about an “ I can’t believe this is our life type moment”.


Christkindl Market

Small wooden handicraft stalls and twinkly Christmas lights stand in stark comparison to the large skyscrapers surrounding them.  Modeled after the traditional holiday markets in Germany the Christkindl Market is an undeniable pop of holiday cheer to anyone walking past. The stalls are filled with delicious smelling German classics like potato pancakes, hot cider and of course, bratwurst. There are some ornaments and other handcrafts being sold but to be honest we came for the food. Prices were ranged from about $2 for a cup of cider, $8 for spiced pecans and $8 for three potato pancakes with the usual sides.

Woman at Chicago christmas Market

Macy’s Holiday Traditions Tour

Macy’s has been an integral part of Chicago holiday traditions for years. While we were on the Holiday Traditions Tour we even here other guest talking about having tea with parents and grandparents each year in the Walnut Room. On the tour, you get some insider information on the famous window displays and Thanksgiving Day Parade. What makes it feel special is the way they guides deliver the history, its like they are letting you in on a Christmas secret.

Magnificent Mile

During the holidays the word shopping makes a brief transformation from assumed self-indulgence to act of love. Gift giving, hours spent browsing the shelves to find the exact item to express your love. There is no better place to shop in Chicago than the 460 retailers represented along the Magnificent Mile. Do not let yourself think it’s all luxury brands here, there are stores for every budget.

Lincoln Park ZooLights

Meg and I attended DC ZooLights and had the most magical little date night. When we found out Chicago has Lincoln Park ZooLights we knew we had to fit into our schedule. This is hands down the fest free holiday activity in Chicago. The Zoo is lit up with over 2 million holiday lights! Check out the schedule for a handful of specialty nights scheduled throughout December.

Illumination at Morton Arboretum

Take a mile walk through the interactive light displays during Illumination at the Morton Arboretum. All the trees are lit up in beautiful ways and Christmas music is flowing through the speakers. Honestly, this is the perfect winter date night in Chicago. I recommend a hot drink and s’mores by the fire for the finishing touches to a perfect evening. When planning keeps in mind they are closed every Monday.

Millennium Park Ice Skating

Possibly the most iconic place to visit in all of Chicago is  Millennium Park, home of “The Bean”. One little-known fact is that The Bean’s real name is the Cloud Gate. Nab the most famous mirrored selfie for your Instagram feed. Pro Tip: get some of the Chicago Skyline in there to avoid the bathroom selfie look. Dust off the skates before you go because there is no more beautiful place to ice skate in all of Chicago. It is free to get on the ice if you have your own skates and about $15 if you need to rent them for an hour.


Holiday Lights and Architecture Tour

Architecture tours in Chicago are the number one tour in Chicago. The Chicago Skyline is widely considered one of the best in the world, it is an epic combination of unique history and modern skyscrapers.  Many people love to get out on the water and take the tours by boat. In the winter the boats don’t run, honestly, it’s just too freaking cold for that. So swap out the boat and add in sparkly holiday lights and you end up with the Holiday Lights and Architecture Tour.

Christmas Around the World at Museum of Science and Industry

The Museum of Science and Industry is jam-packed with exhibits of all types. What instantly jumped out to me was the attention to detail paid in making sure information was presented in ways that people with various learning styles can consume. As a physical learner myself I often find it hard to get through museums but absolutely loved my visit here.

The main exhibit was Christmas Around the World, showcasing 50 trees! Each tree was decorated to highlight traditions and customs from around the world. As a traveler I found it fascinating to check them all out, attempting to gain even the slightest idea what it would be like to celebrate in cultures so different from my own.  

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