Eye icon to see Chicago architecture

Architectural eye candy

4 or 8 hours

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11 or fewer guests

Expert tour guide

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Best Chicago highlights

Downtown Bucket List
Private Tour

Experience the best of the Loop and Mag Mile

Our signature, four-hour experience is half by chauffeured car and half by foot in order to maximize both the quantity of sights and the quality of your experience. You can also go full blast with your Chicago sightseeing on a full-day tour.

Your professionally trained tour guide will reveal Chicago’s bold character through its dramatic landmarks and fascinating backstories. You’ll hear stories of history, new ideas in architecture, and insights into contemporary Chicago life.

Your chauffeured driving tour will give you a macro perspective of the city. You’ll see historic skyscrapers, grand mansions, modernist buildings and the skyline from Museum Campus.

The walking tour within the Loop gives a more up-close look at Chicago. You’ll visit the Riverwalk, the Magnificent Mile, and dazzling interior spaces like the Chicago Cultural Center with its Tiffany stained-glass dome.

We’d love to be your Chicago expert guide on history, architecture, food, drinks and things to do. Discover why our passionate tour guides got us runner-up for “Best Tour of Chicago” two years in a row.

Chicago Highlights Tour visits Lincoln Park lagoon Nature Boardwalk
chicago highlights private tour


  • See Chicago highlights on a 1/2 driving tour, 1/2 walking tour.
  • Marvel at dramatic skyline views.
  • Learn about famous and overlooked architecture.
  • Drive through the Gold Coast’s enclave of historic mansions.
  • Cruise down Michigan Avenue, aka Mag Mile.
  • Step inside glitzy lobbies of the world’s oldest skyscrapers.
  • See the Muddy Waters mural and learn about Chicago blues.
  • Enter draw-dropping landmarks like the Cultural Center.
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Meet your private Tour Guides

Alex Bean

"I love showing how buildings are physical remnants of history that let us in the present have a glimpse into the past. I'll show you forgotten pieces of the past, like the cowpath through a luxury hotel in the Loop."

Amanda Scotese

"I am fascinated with how every downtown building has a story to tell, both about its design and the people who have used it. I can take you to the best spots for a Chicago-style hot dog, donuts or hot chocolate."

Marie Rowley

"I love introducing newcomers to Chicago highlights and revealing the city's secrets to local Chicagoans. As your tour guide, I'll incorporate stories of the diverse people who have made downtown Chicago."

why our private tours are the best

Our team of expert tour guides know how to curate a killer experience. We’ve been top-rated since 2010 on TripAdvisor and Yelp.

We have hosted more than 75,000 tour guests. We love to bring curious people to explore stories and places even locals don’t know of Chicago history, architecture and culture.  

private downtown tour in lobby
Can’t say enough about this tour - an absolute blast.
We have so many great memories from the tour and we learned a lot.



Private group tour rates start at $45 per person.
We can also accommodate large groups of hundreds via bus.
Call us: 312.350.1131
Email us: sales@chicagodetours.com





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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