Our New Neighborhood, Food & Bar Tours

We are excited to bring you three new private Chicago neighborhood tours. Chicago is, after all, a city of neighborhoods. Each of these tours explores the history, architecture, and food created by the people who live in these distinct, though ever-changing, areas. Think outside of downtown. Think outside of deep-dish and Italian beef. Heck, think outside of your grandmother’s tour!

Big Shoulders food bus tour neighborhood bar Bridgeport Chicago Detours South Side tour
Neighborhoods are the best places to find historic bars in Chicago. Photo by Pawel Skrabacz.

Big Shoulders

Don’t call it a comeback–Bridgeport’s been here for years. We are excited to share stories of old Chicago on a new route. After the closure of Schaller’s Pump (RIP) we had to rethink our tour of Chicago’s oldest neighborhood, Bridgeport. We are excited to re-release this popular bus tour.

This South Side tour includes three drinks at historic bars paired with food that help tell the tumultuous story of this blue-collar neighborhood and Chicago itself. From Upton Sinclair to Da Mayors Daley (to only name a couple), Bridgeport is chock full of characters. Historic bars, new cuisines to the neighborhood like bao, and old favorites like the dreaded mother-in-law sandwich, make this a complete, authentic experience for locals and visitors alike.

Chicago neighborhood tours pilsen food
Did I mention our Pilsen Tour includes food? Photo by Pawel Skrabacz

Changes and Spaces in Pilsen Walking Tour

Pilsen is at the heart of some of the most interesting conversations happening in Chicago. For decades Pilsen has been a working-class neighborhood, first as a Czech enclave before developing into the heart of the Mexican community in Chicago. Now it exemplifies the contentious process of gentrification that is changing our cityscapes. Guests on this tour consider these changes while viewing politically-charged community murals juxtaposed with trendy street art, and contemplating the irony of “gourmet” tacos, which were once considered working-man’s fuel.

Experience this South Side story for yourself on this Chicago neighborhood tour by foot. Dig into the history, architecture and culture one of Chicago’s most vibrant neighborhoods while tasting authentic dishes at neighborhood spots on this walking tour.

On this bus tour, guests have opportunities to get close to Logan Square street art. Photo by Marie Rowley.

The Future of Cities in Avondale & Logan Square Tour

Major U.S. cities are changing, and Chicago’s neighborhoods provide clear examples of this. Whether good, bad or just difficult, it’s worth seeing these changes. On this bus tour, guests will look at the architecture and landscapes of Logan Square and Avondale. These areas used to be known as the Polish Village, but it’d be hard to guess that history these days. We briefly de-board to get up-close and personal with street art. Along the way, guests learn to read the signs of shifting communities. This tour concludes the same way most good experiences in Chicago do–with a stop at a neighborhood bar for drinks and discussion.


– Morgan Lott, Private Tour Coordinator and Tour Guide


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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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