Best Chicago Architecture Tours Pt. 1: Breadth

Without question, a visit to Chicago would not be complete without a tour of the best Chicago architecture, soooo…which one? The choice of breadth or depth will be your first choice to make. By “breadth” we mean trying to see lots of places and buildings, versus getting an in-depth background on fewer ones. In other words, the breadth kind of a tour will look at architecture from a distance and with speed.

Your preferred mode of transport will be the next decision. For breadth, you will go for a bus tour, boat tour, or Segway tour. For a tour with depth, which will be in Part 2, your best bet for a Chicago tour would be by kayak, bike, or a walking tour. Here’s a little guide to help you find the best Chicago architecture tour for your travel style, from the perspective of a tour company, Chicago Detours.

Boat Cruises

chicago skyline museum campus tours best Chicago architecture
A “macro” view of the Chicago skyline from Museum Campus

Architectural boat cruises reign as the absolutely most popular way to tour Chicago architecture, at least during the summertime. Chicago’s First Lady Cruises or Chicago Line Cruises offer comprehensive learning experiences. Those who want a more lively, entertainment driven tour can try Wendella Sightseeing Boats, Chicago’s Skyline Cruiseline, or Shoreline Sightseeing Company.

Whichever architectural boat cruise you choose, the experience of the tour will be primarily a visual one. The pace of the slow-moving boat is not unlike panning in a film.

It’s like a 360-degree movie screen surrounds you as you sit in your chair and slowly glide by the skyscrapers. Guides will share brief commentary about the history and styles of the architecture. It’s a moving tour, so there’s just enough time to move on to another spectacular angle.

Segway Tours

For another experience of the best Chicago architecture you could try a Segway sightseeing tour. To be totally honest with you, I’ve always been mystified by the allure of this mode of transportation. They look utterly ridiculousness whizzing among Renaissance architecture in Florence. There is a slew of Segway tour companies to choose from: Absolutely Segway, City Segway Tours, Segway Experience of Chicago or Steve’s Segway Tours. The fun of the Segway tour is zipping through the city in such a unique way. Absolutely Segway Tours offers a weekend architectural tour through Grant Park, culminating with the grand skyline view from the Museum Campus. That sounds pretty cool!

Bus Tours

chicago bus tours
The bus we use for our Jazz, Blues & Beyond tour

For some, a bus tour is the best Chicago architecture tour for their tastes. Bus tours of the city by companies like Chicago Trolley & Double Decker allow you to get a general overview of the city – and also possibly a tan – while viewing the architecture from the unique perspective of elevated above street-level. Bus tours are the quickest and most general way of experiencing Chicago architecture. Honestly, I only recommend them to people with mobility issues. If you really want to see Chicago via wheels and with air-conditioning, grab a guidebook, like the AIA Guide to Chicago, and get a CTA pass to tour the city by public train and bus.

Ultimately, your experience is whatever you want it to be. Have fun touring Chicago, and stay tuned for Part 2 on “depth.” We’ll highlight the city’s walking tours, running tours, bike tours, and kayak tours!

— 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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