Festive Tales and Traditions: A Chicago Christmas Tour
About the Tour
Chicago transforms into a winter wonderland during the holiday season. On this walking tour, you’ll discover why centuries of innovation and tradition made this city America’s unofficial Christmas capital. You’ll also find out how immigrant communities shaped the city’s holiday celebrations.
Starting beneath the historical Marshall Field and Company Building’s clock, you’ll walk through downtown Chicago’s most festive neighborhoods. During the holidays, you’ll pass Marshall Field’s richly decorated windows that have enchanted visitors for over 100 years. Continuing through the heart of the Chicago Loop, you’ll hear tragic Christmas stories and see Palmer House, a Hilton Hotel, where the brownie was invented for the 1893 World’s Fair.
The tour ends in Maggie Daley Park where, in winter, you can watch skaters glide along scenic paths with views of the Chicago skyline. Along the way, you’ll understand how German immigrants brought Christmas markets to America and find out why Chicago claims to be the birthplace of Rudolph the Red-Nosed Reindeer.
On this 45-minute tour, you’ll have a chance to:
- Learn about the tragic Iroquois Theatre fire of 1903 that changed theater safety codes nationwide
- Hear about the festive atmosphere of Christkindlmarket Chicago, America’s largest Christmas market
- See Marc Chagall’s ”Four Seasons” mosaic and find the winter scene among its colorful panels
- Spot the Holiday ’L’ train decorated with twinkling lights as it passes overhead
- Meet the Art Institute’s bronze lions, wearing their festive holiday neckties
- Find out how this urban transportation hub shaped holiday traditions, from Christmas tree schooners to Route 66 adventures
By the end of this tour, you’ll have experienced Chicago’s holiday magic through several stories about the diverse communities that created one of America’s most beloved Christmas traditions.
This tour can be enjoyed year-round but is particularly special during the holiday season.
Tour Producer
Amy Bizzarri
I’m Amy Bizzarri, a Chicago-based storyteller and educator. I'm also an armchair historian, PADI-certified scuba diver, yogini (and certified yoga instructor), mom, and mermaid (proud graduate of Weeki Wachee Mermaid School), not necessarily in that order.
My deep Chicago roots trace back to an extraordinary family legend: my great‑great‑grandparents met on the night of the Great Chicago Fire, when volunteer firefighter Walter Daker mistook young Catherine’s flowing ginger hair for flames and swept her up in his arms, literally and figuratively. I'm the author of a few Chicago history‑focused books, including Discovering Vintage Chicago, Chicago’s Iconic Dishes, Drinks, and Desserts, and 111 Places in Chicago That You Must Not Miss. I live in a century‑old home in the Logan Square neighborhood.
In my 20s, I lived in Italy, where my family has roots (Felina, RE). I'm an expert in all things Italy.
I speak fluent Italian and French; excellent Spanish and Portuguese.
My love for wine led me to pursue Wine and Spirt Education Trust (WSET) sommelier certification, levels 1-3.
I love a great road trip, too. So much so that my book The Best Hits on Route 66 earned the 2019 Silver Lowell Thomas Award for Best Travel Guide from the Society of American Travel Writers. I followed that bestselling guide with The Best Hits on the Blues Highway, which explores U.S. Route 61, the storied road that shaped American music. My latest book, Route 66 Recipes, celebrates the history behind the diners, dives, and restaurants along the Mother Road as it approaches its 100th anniversary in 2026.
1,000s of children have passed through my classroom doors over the years. I'm a dedicated educator with over 20 years of experience, holding a Master of Arts in Education with a focus on bilingual education. I'm Reading Apprenticeship and International Baccalaureate-certified, endorsed in ESL, and I've been awarded several study grants from the National Endowment for the Humanities (2019, 2021, 2022, 2023).
My storytelling has expanded beyond the page: I've hosted local and national television/radio segments, and I've produced interactive smart walking tours with VoiceMap and EAtlas.
Follow my adventures on Instagram at Instagram.com/amybizzarri to see where in the world I am today!
Preview Location
Location 1
Start - Marshall Field's Clock - 111 N State St
Our tour begins here, under the historic Marshall Field's Clock. This iconic t... Read More
How VoiceMap Works
Major Landmarks
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The Art Institute of Chicago
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Miller's Pub
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Palmer House a Hilton Hotel
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Maggie Daley Park
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Macys Chicago
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Millennium Park
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Chagall's Four Seasons
Getting There
Route Overview
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Start location111 N State St, Chicago, IL 60602, USA -
Total distance2km -
Final location337 E Randolph St, Chicago, IL 60601, USA -
Distance back to start location690.68m
Directions to Starting Point
Our tour begins 'under the clock' at Macy's (formerly Marshall Field's), on the northeast corner of State Street and Washington Street.
Tips
Places to stop along the way
There are many opportunities to stop at different places along the route.
Best time of day
For the ultimate experience, we recommend taking the Christmas in Chicago Holiday Walking Tour between 10 AM and 7 PM. During these hours, you'll be able to fully enjoy all the sites, as they will all be open for operation.
Precautions
The area is safe but always be street smart and take care when crossing busy intersections.
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