Detours 2021 Chicago-themed Gift Guide

Upon us is our annual tradition of the Chicago Detours curated gift guide, a compilation of Chicago-themed gifts for friends and family. These gifts are great for born-and-bred Chicagoans as well as new transplants. We choose gifts that specifically highlight Chicago architecture or history, or show off Chicago pride. Support local businesses with these Chicago gifts this season!

Gift #1. Artwork of Chicago Neighborhood Landmarks by Ruth Pychke

ruth home art studio kingston mines paintingI chanced upon artist Ruth Pycke Pomareda on Instagram and was struck by the energy of her acrylic paintings of Chicago buildings, from neighborhood landmarks to the iconic skyline. Her Chicago paintings do get snatched up pretty quickly! Pictured here is a little bit of a departure from her more architectural paintings. It’s a blues musician at the venerable Chicago blues club, the Kingston Mines.  She also does paintings of Wrigley,  Guaranteed Rate and Soldier fields, and other sports themes for the Cubs or White Sox fan in your life. 

If you are near the Lincoln Park neighborhood, her artwork will be on display until May of 2022 at a gallery called Fortunate Discoveries. Find it located on Armitage just west of Sheffield. Ruth also takes custom orders at very reasonable rates! Email her at Snatch up her paintings off Facebook or Instagram  (@myhomeartstudio90) for around $90

Gift #2. Learn and Reflect with the Badass Women Journal

badass women journal 2020 shop local gift guide

We at Chicago Detours designed the Badass Women Journal to inspire and inform curious people about Chicago women from history. The 52-page printed journal has blank pages along with vibrant watercolor illustrations and the backstories of eight badass women – like Bessie Coleman, who was the first licensed Black pilot, or Maria Tallchielf, who was America’s first prima ballerina.

The blank sheets of this journal are great for notes, reflective writing, or drawings. Some pages have inspiring quotes by well-known heroes like Ida B. Wells and Michelle Obama. Journal book for $16.

And while we’re at it – Chicago Detours also has a few dates for our “Downtown Chicago Holiday Walking Detour” available for public and private groups. See all the tour dates here

Gift #3. Books from Da Book Joint

Support a female, Black-owned business in Chicago with Da Book Joint, a

simon b rhymin book cover for chicago gift guide

 marketplace of African American books. It has a physical location in Boxville, a shipping container retail market and business incubator.

Consider Simon B. Rhymin’ by Dwayne Reed for the creative kid in your life. It’s a storyabout a fifth grader who dreams of being a rapper and ends up facing his fear of speaking in front of people and ends up using his voice for positive change.

book gift cover three girls from bronzevilleA great Chicago gift for women intrigued by personal stories and Chicago history is Three Girls From Bronzeville. It’s a memoir by former Chicago Tribune columnist Dawn Turner. Just published in fall of 2021, this work of nonfiction “has given us a tutorial of urban decay, White privilege, poor city planning and the influence of fads and digital advances on Black urban teenagers,” according to the  Washington Post. And of course, the book takes place in the South Side neighborhood of Bronzeville. Books are various prices, and make sure to buy from Da Book Joint.

Gift. #4. Where the Tour Buses Don’t Go Book by Gerry Lekas

chicago gift book of chicagoland historyThe rather comprehensive book title pretty much explains it: Where the Tour Buses Don’t Go: Chicago’s Hidden Sites of the Mysterious, Macabre, Ghostly & Glamorous. It is a manual for self-guided car trips around the Chicagoland area in search of the more eclectic, little-known spots that might hold an appeal for fans of all-things Windy City odd. Be clear that it has a lot of suburbs included in this book. Consider it a “Detour from Chicago” and a broader exploration of the Chicagoland area.

Paperback book for $12.93.

Gift #5. Brick of Chicago 2022 Calendar

calendar brick of chicago giftWill of Brick of Chicago is an architectural photographer, writer and researcher. He loves bricks! His Instagram account (@brickofchicago) documents the incredible variety of Chicago brick patterns and textures. 

The 2022 Brick of Chicago Calendar highlights buildings from a variety of Chicago neighborhoods, including Logan Square, Roseland, McKinley Park, and Lakeview. And it has a very pretty letterpress cover. Buy the 2022 Calendar here for $15.

Gift #6. Miscellaneous Chicago-made Gifts

chicago el game gift guide for holidaysTry out Local Goods Chicago for even more Chicago-themed gifts, from tea towels printed with Chicago symbols to Chicago star ornaments or the Chicago El game, pictured here.

We have just a few dates left for our “Downtown Holiday Walking Detour,” an in-person, mostly indoor walking tour. You can grab a friend and join a couple of our public tour dates or book for a private group. Public tour $50 per person, private tour $60 per person

Have an excellent holiday season! And thank you again for supporting our Chicago content and tours for curious people here at Chicago Detours. 

– 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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