The Best Free Rooftop Views of Chicago

free rooftop views Chicago Fine Arts Building

We want to highlight the best free rooftop views of Chicago. After all, paying for cover and drinks at the swanky rooftop bars isn’t exactly cheap. You can still get that sweet skyline view on the cheap, though! Heading into famous and overlooked buildings and finding a hidden vista is one of the great downtown […]

Overlooked Historic Architecture on the Mag Mile

World-famous skyscrapers bookend the Magnificent Mile and the Water Tower is a legendary presence, but today I want to highlight some of the lesser-known historic architecture on the Mag Mile. They don’t call us “Chicago Detours” for nothing! Of course the architectural boat tours talk about the Wrigley Building and Tribune Tower, and your hop-on […]

Explore Printers Row Architecture During Lit Fest

Printers Row, a section of the South Loop with historic architecture related to the printing industry, will become the most dangerous part of Chicago this weekend for book lovers. The neighborhood is hosting the 34th Annual Printers Row Lit Fest. Here I have made a brief guide of some of the Printers Row architecture highlights you can […]

How Do We Reckon with Orientalist Architecture in Chicago?

Bahá'í House of Worship Wilmette Orientalist architecture in Chicago most beautiful buildings in Chicago

Chicago is famous for its different schools of architecture. The First Chicago School created the skyscraper and gave our city its architectural identity. The Second Chicago School, the Modernists of Mies van der Rohe with their austere steel and glass facades, completely redefined how we think of buildings. Today, contemporary architects like Jeanne Gang blaze […]

Presidential Architecture and History at the Blackstone Hotel

The Blackstone Hotel, known as the “Hotel of Presidents” has long been one of the most prestigious spots in Chicago. Located on Michigan Avenue in the South Loop, where we often lead custom private tours, the grand hotel has hosted a dozen U.S. Presidents and countless celebrities, such as Marilyn Monroe, since its construction in […]

Chicago History Books for Your Holiday Gift List

Chicago History books The Dial bookshop

It’s hard for me to imagine a better holiday gift than good Chicago history books. They hold the promise of gripping narratives, undiscovered facts, and greater perspective and understanding. It’s like manna from heaven for big ol’ history and architecture nerds, like yours truly. But which Chicago history books are worth gifting? To help you […]

Five Ways to Appreciate Chicago’s Historic Buildings

Chicago's historic buildings Reliance Building virtual events remote team building

Chicago’s historic buildings are a three-dimensional manifestation of our city’s history and culture. If these buildings could talk, they would have endless stories to tell about the city and the many people that have passed through. Read here to learn how to better understand the architecture around you, and imagine, if Chicago’s buildings were among the […]

Underground Chicago: Exploring The Hidden Layers of the City

underground Chicago lower Wacker Drive

The term ‘Chicago architecture’ usually evokes images of soaring skyscrapers, but the architecture of underground Chicago is fascinating and essential in its own right. Virtually unknown layers of tunnels, passages, sewers, pipes, and other infrastructure crisscross below the city.  We research stories from Chicago history, architecture and culture like this while developing our live virtual tours, in-person […]

Questions from our World’s Fair Tour on Today’s Anniversary

World's Fair Tour guest questions

In the 18 months since it launched, we’ve had tons of guests discover a huge piece of Chicago’s history on our “1893 World’s Fair Tour with Bars.” As anyone who has joined us knows, our guides always encourage questions from guests. Accordingly, we’ve been doing some fun research on the questions from our World’s Fair […]

Why the Chicago Architectural Boat Tour is So Popular

chicago architectural boat tour

Earlier this summer, TripAdvisor named the Chicago architectural boat tour the single most popular tour in America. That got me to wondering, what is it that makes it so popular? Sometimes our walking tour guides are hired out to lead a Chicago River boat tour, often on a private yacht charter via Anita Dee Yacht Charters. […]

Ellen

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.”
Robert
GetYourGuide

Jen

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.”
Heather
TripAdvisor

Elyse

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.

Anthony

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.

Marie

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.”
Lorit
TripAdvisor

Sonny

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
TripAdvisor

Alex

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
Yelp

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
Yelp

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