Best Chicago Architecture Tours Pt. 2: Depth

In choosing a Chicago architecture tour, you have so many choices that I decided to split the post into two parts. Part One considers the idea of “breadth” in a tour. We can choose to cover a lot of geographical ground and see a lot in an architectural tour, but not delve so much into deeper concepts of Chicago architecture and history. For “depth” you will see much less, but the tour guide will share more backstory on the buildings you will see to create a more educational experience.

kayak tours in chicago river
Tour Chicago via kayak with companies like Urban Kayak

Boat Tours

Generally the architectural boat cruises move by buildings so quickly you cannot really absorb more than a fleeting impression, so for a more active boat tour and a closer connection to the river, you could venture into a kayak. Urban Kayaks, Kayak Chicago and Wateriders are your options for kayak tours. Because you’re down much closer to the river, the buildings will seem even bigger and the slower pace will allow for more eye-candy time. However the tour guide commentary may not necessarily be so in-depth on these tours, which are often billed as “architectural tours,” simply because of the logistics of the tour group being in multiple boats.

Bike Tours

Chicago bike tours can cover a good amount of space in a short amount of time. Plus you get the lake wind blowing through your hair! Bike tours provide the sights and sounds of the city. Part of the allure also comes from the freedom to explore. Bobby’s Bike Hike has a Lakefront Neighborhoods Tour that ventures along the more residential side of the Mag Mile. It ultimately reaches the tiny side streets of the Old Town neighborhood. You even get to hop off your bike and see the nooks and crannies of the neighborhood on this Chicago architecture tour. night owls, their “City Lights at Night Tour” rolls by Gold Coast Mansions to the aforementioned Museum Campus view.

Running Tours

For the most active option of tour, go for a run! City Running Tours takes you for a jog while telling you grand stories of Chicago history, primarily along the lakefront. I’ve been meaning to try this out for some time, actually. I loved running when I used to work as a tour guide in Italy. It gave me a great perspective on the city I was in.

Architecture of chicago tours macys columns

Walking Tours

The slowest and most in-depth way to explore architecture is of course by foot. Walking affords you the time to soak in the beauty of architectural detail of building exteriors and the possibility to step into magnificent lobbies and contemporary interiors. Joyce Walks Chicago ventures into neighborhoods like Chinatown. Chicago Architecture Foundation has a multitude of docent-led walking tours that visit anywhere from the mansions of Astor Street to the Palmer House Hotel to Wicker Park, and tend to focus on the technicalities and styles of architecture. Multiple tour companies offer Pedway tours of our underground system of passageways. Or stop by the Chicago Cultural Center to pick up a Chicago Greeter, a year-round walking tour service that gives visitors the opportunity to explore Chicago with a volunteer leading the way. What hospitality Chicago gives, right?!

chicago architecture interior tour
Explore Architectural Interiors on the “Inside the Loop” tour

For in-depth perspectives on actively, visually engaging with our surroundings and how to relate to architecture, try my company, Chicago Detours. Our highly trained guides are experts in Chicago history and architecture. They’ll take you inside buildings to see the workings of the city and the beauty of interior architectural spaces. In order to understand architecture, we have to step inside. Architecture can be as much about the spaces we inhabit as the structures that surround us.

— Amanda Scotese, Chicago Detours 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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