Things to Do in Chicago Thanksgiving Weekend

Around the holidays in Chicago, a lot of the transplants head out and an influx of families come in. While things to do in the neighborhoods may shut down, downtown lots is left for fun activities. A few great things to do this Chicago Thanksgiving weekend:

1. Avoid Macy’s at all costs. It will be a zoo.

chicago tours architecture history in temple building

2. An interior architectural tour with yours truly, Chicago Detours

The Loop Interior Architecture Walking Tour avoids the cold (high of 43 degrees for Friday, only 36 for Saturday) by staying indoors to explore a very striking variety of buildings: a modernist structure, a church in a skyscraper, the dazzling mosaics of the Cultural Center. It’s not about dates and names of architects and events in history – it’s about the people and stories that make Chicago great. Friday 3pm, Saturday (SOLD OUT) & Sunday 1:30pm.

3. Christkindlmarket

It officially opens today! The annual German-style market with gifts, sausages, and best of all – you can drink beer or spiced wine called gluhwein in the middle of Daley Plaza.

4. Thanksgiving Day Parade

Starts at Randolph and ends at Congress along State Street on Thursday morning. According to their website, they will have “decorative floats dispensing holiday cheer.” Giant inflatable balloons will also contribute to the joy and terror of both children and adults. Fun fact: the parade started with “dispensing” just any kind of cheer in the 1930s, as it was created to boost morale during the Depression.

5. Fantasia with the Chicago Symphony Orchestra

Disney’s Fantasia will be performed with the original 1940 film screening. Saturday 8pm, Sunday 3pm. chicago thansgiving weekend fantasia cso6. The Historic Chicago Walking Bar Tour

Drink and eat while learning about Chicago’s entertainment history. Stop into a few bars and restaurants you never knew had such fascinating history. It’s a blast. Saturday 5pm, near the Mag Mile area.

Whatever you do, have fun and enjoy time with people you love. And THANK  YOU for reading!

— Amanda Scotese, Executive Director


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Private Tour Coordinator and Tour Guide

There is no shortage of things to discover in Chicago—I love being an urban explorer and uncovering its hidden places. I have an MA in Public History from Loyola University Chicago, and I have worked as a museum educator and kindergarten teacher. My desire to learn new things fuels my passion for educating others, which I get to experience every day as a Chicago tour guide. I live in the northern neighborhood of Rogers Park.

“Our guide Ellen was exceptional and gifted with a great personal touch.”


Tour Guide

Whether you are a first-time visitor or a lifelong resident, the vibrant history and modern majesty of Chicago never ceases to amaze. I’m a graduate of Columbia College with an M.A. in Interdisciplinary Art. I’ve worked for many years as an educator at City Colleges of Chicago. As tour guide at Chicago Detours, I integrate my enthusiasm for culture and architecture with my passion as an educator. West Town/Noble Square area is home for me.

“Jen was a perfect storyteller and kept us spellbound for hours.”


Tour Guide

With our Chicago neighborhoods, vibrant cultural institutions and nearly two centuries of larger-than-life stories, there’s never a dull moment here! I’m a fifth generation Chicagoan and a graduate of Washington University in St. Louis. In addition to guiding tours, I’m a creative writer and amateur genealogist. I also enjoy the city’s dynamic theater scene. You can also read overlooked stories from 19th-century newspapers on my “Second Glance History” blog. I live in River North.


Tour Guide

Chicago is unique as it always evolves into the future while holding on to the past. I’m fascinated by how people latch on to old architecture but happily pave over others. My background is in theater and performance and I’ve been a tour guide here for more than 10 years. Currently I’m finishing my Master’s in Public History at Loyola University because I love to teach the history of this scrappy city. I’m in the Edgewater neighborhood.


Operations Coordinator and Tour Guide

Chicago’s history is so fascinating, you could spend a lifetime uncovering its secrets…I’m willing to give it a try! I have an M.A. in US History from the University of Nevada-Las Vegas and then pursued doctoral studies in Urban History at the University of Illinois at Chicago. I love to learn new aspects of Chicago’s rich history and then share my knowledge as a tour guide with Chicago Detours. I live in Ravenswood.

“Marie was a bubbling fountain of information and contagious enthusiasm.”


Operations Coordinator and Tour Guide

As a fourth generation Chicagoan, I have been living and loving Chicago by bike, on foot, public transit or automobile. I am a graduate of UIC where through the College of Urban Planning and Public Affairs, began my eagerness to understand the nature, history and impacts of urban planning and development. It is incredibly rewarding to give back to this wonderful city by helping out in the office of Chicago Detours. I live in the incredibly diverse neighborhood of Albany Park.
“Sonny was extremely knowledgeable about all things Chi-town.”
Wade K


Content Manager and Tour Guide

Chicago has so many neighborhoods, buildings, and by-ways that it’s hard to go long without seeing something new, or something familiar from a new angle. I studied Cinema History for my M.A. from the University of Chicago. I’ve worked as a culture writer for various publications and as an educator of the humanities at the City Colleges of Chicago. I’m thrilled to share my love of this city’s busy past and unique architectural spaces with Chicago Detours. I live in the Chicago neighborhood of Lincoln Park.

“Alex was fascinating to listen to. He clearly knows his history and it shows.”
Katie K

Amanda Scotese

Executive Director and Tour Guide

I’m an interpreter of personal stories from the past and the city’s landscape. I love to imagine what originally happened inside old unmarked buildings, and what forces have shaped their design. I studied Chicago history, architectural history, and anything Chicago-related through my M.A. in the Humanities at the University of Chicago. My love for stories was enriched by my B.A. in Literature from the University of Michigan. I’ve written travel articles for publications like Rick Steves’ Italy best-selling travel guides, the San Francisco Bay Guardian, and The Chicago Food Encyclopedia. I live in the Chicago neighborhood of West Avondale.
“You can TELL Amanda is hyper-passionate about doing the research and getting the story that nobody’s heard before.”
Shelby F

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