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Three Chicago Holiday Traditions and One New

By Alex Bean on December 17, 2015


Like millions of other Chicagoans, I love the unique festivities and special Chicago holiday traditions. Here are some of our favorite activities to celebrate the holidays in Chicago this season.

Chicago holiday traditions Marshall Field's
A visit to the former Marshall Field’s is a Chicago holiday tradition.

Window Displays at Marshall Field’s

These dioramas have been one of the leading Chicago holiday traditions since they first enchanted kids of all ages in the 1890’s. The Field’s brand was retired when the store was bought by Macy’s, but the tradition continued and each window draws a sizable crowd throughout the holidays. In my own experience, it can be just as magical (and maybe a little easier) to go up to the 7th and look in on the glorious Christmas tree in The Walnut Room. You can check out both the window displays and The Walnut Room on our annual Holiday Tour of Drinks, Daleys and Dead Guys.

Christkindlmarket in Daley Plaza

The annual Christkindlmarket in Daley Plaza has been a Chicago holiday tradition for less than 20 years. Folks always love seeing it during our Loop Interior Architecture Walking Tour during the holiday season. The open-air market is based on the original in Nuremberg. That festival began in 1545, so it might be a while before we in Chicago catch up.

At Christkindlmarket, you can buy special holiday gifts like ornaments, knit hats, and also genuine German food like currywurst or apple strudel. It’s now become more international, too, with stalls from Poland, France, and South America. We have some tips for finding the right sausage, sweets, and stocking stuffers.

A great joy of the Christkindlmarket is getting the souvenir boot filled up with mulled wine, called gluhwein. Have you ever wondered what ingredients are in it?

As I can attest from my visit this year, the crowds at Christkindlmarket can be immense and dense. Go on the weekend only if  you dare!

The CTA Holiday Train

One of my favorite Chicago holiday traditions started riding the rails in 1992. The famous holiday train is a beloved CTA instution after 25 years. One very special ‘L’ train is decked out with holiday lights, blasting music, with a flatbed open-air car for a real live Santa, his sleigh and his reindeer.

Sadly, I’ve yet to hitch a ride on Santa’s sleigh this year. We’ll blame bad luck and worse timing. But we could hear its music and announcements out our office windows in the Loop last week, which was a treat.

Chi-Town Rising

A new Chicago holiday tradition is launching this year. The Hyatt Regency is hosting a New Year’s Eve celebration named Chi-Town Rising. The giant party on the riverfront will bring in musical acts and celebrity hosts and will simulcast the celebration on NBC5 and Telemundo. Time will tell if it catches on and becomes another Chicago holiday tradition.

— Alex Bean, Chicago Detours Tour Guide


Chicago Detours offers guided walking and bus tours of architecture, history and culture to public and private groups. We are a passionate team of educators, historians, artists and storytellers, and are proud to be one of very few tour companies in Chicago that is rated five stars on both Google and TripAdvisor.


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