Group Urban Excursions (aka Private Tours)

2022 Update: We no longer offer public tours and have kept this post as a historical record of our role in innovating in travel and tourism.

Lately we’ve been bombarded by interest in our private tours of Chicago, and it probably comes along with the surge in interest in unique experiences these days. (FYI, we can create custom tours for private groups.) Groupon and other deals’ business models depend on this trend. Ten years ago activities for grown-ups didn’t have this kind of hype. Apparently lines go around the block to tour Chicago first local distillery Koval, located in Lincoln Square, and new twists on the tour, like the Chicago Beer Experience or Urban Kayaks, show that Chicago Detours isn’t solo in the lands of hipper travel. Allow images to see a cool picture

What’s On Our Private Tours

Here is a picture of a crew from a digital agency called Doejo. They came on a “field trip” with Chicago Detours on our Loop Interior Architecture Walking Tour. Several of them were recent transplants to the city and hadn’t seen much yet. This indoor walking tour of architecture, history and culture opened them up to the beauty of downtown – and to the idea that tourism doesn’t have to be hokey.

We’ve done private tours for groups ranging from corporate team building outings to family reunions, and from every tour we learn a little something more about catering our tours to the interests and expectations of our guests. What do I mean by this? Well, when we do a family outing, we keep things real casual and roll with the family’s style of sense of humor and personal interests. Law firm groups are impressed when we bring out Release Form Contracts for them to sign. And when I hopped on a boat with a private group from Morningstar and mingled to answer Chicago questions, I realized that financial types wanted more facts and figures than stories from history (one even asked me how much water is in Lake Michigan!). I had a woman from the Upper West side of Manhattan hire me to take her, just her, on a four-hour tour by hired car to experience Chicago history – but in chronological order. We haven’t had too strange of requests so far – at least not yet.

Public/Private Divide

Our private guided tour options include our tours that we’ve offered to the public. The Loop Interior Architecture Walking Tour takes guests on an indoor excursion of a variety of sites downtown. While lots of locals have seen the sparkling Tiffany mosaics of the Chicago Cultural Center. Many haven’t heard the insider stories our knowledgeable guides share. We also tour the mythic Pedway network of underground passages. These explorations balance with in-depth discussions on architectural design and city development follies.

We are just now beginning to offer our Historic Chicago Walking Bar Tour to groups. This guided walking tour, which takes place 90% indoors, includes three stops for beer or wine in restaurants of eras past. Just like the Loop walking tour, guests get to share iPads with historic video clips and photos. We pop into a couple examples of roaring ’20s opulent architecture and dig into stories of prohibition, social clubs, early jazz, vices and nightlife. It’s all just north of the Michigan Avenue bridge. We include appetizers at two of the stops, too, making it part food tour, part history tour, part architecture tour.

Musical Private Tours?

Tips for planning a Chicago Family Reunion private tours
A family reunion on our Jazz, Blues and Beyond Tour last summer. Photo by Amanda Scotese.

Groups looking for a premium experience love our Jazz, Blues, and Beyond Bus Tour. This tour (actually more like “luxury coach tour”) goes to neighborhoods north and south to expound the cultural history of Chicago’s most influential music. We even have a blues musician hop on the bus and teach blues harmonica.

And lastly, we do all kinds of custom tours for private groups. We’ve customized the Jazz and Blues tour to include dinner at a soul food restaurant. We’ve built a green tour of Chicago that shares thoughtful perspectives on the entire green movement, from architecture to food. And we’ve offered historic pub crawls by bus, a Pedway pub crawl, and creative food tours for our private tour guests.

Give Us a Call!

Tours with a private guide in Europe are pretty standard, but Americans like to think that they already know everything! A live tour guide has more enthusiasm and insights than a guidebook or iPhone app. And we also take tour guiding as not a hobby, but as a profession. That’s why our tours are great for all kinds of local business groups. Lawyers love the learning, creative professionals love the visual experiences, etc. Plus, everyone enjoys getting out of the office and exploring our incredible city.

 — 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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