Best Tours to Get to Know Chicago for New Chicagoans

We welcome you new Chicagoans to Chi-town. The Second City. The City of Big ShouldersThe City That Works. Urbs in Horto. The Windy City. Any city with that many names contains multitudes of experiences. It’s probably impossible to ever fully know Chicago, but Chicago Detours offers public tours that you can individually sign up for, or these four private city tour experiences can acquaint you with this evasive mistress. 

Chicago Blues Tour Fun Bus Tour Laughing Chicago Detours get to know Chicago city tours

1. The Best Chicago Highlights Tour

While there are a lot of different “highlights” city tours in Chicago, only one Chicago Highlights Detour 101 Tour by Bus exists. We at Chicago Detours emphasize quality over quantity. Though it could be argued that every skyscraper, park, corner, avenue, and alley (we have the most in the nation!) of this fair city is a highlight, we’ve whittled down this two-hour tour experience to touch upon the best of the best highlights. This city tour has been curated to hit the Chicago highlights and we also share an in-depth perspective on the trajectory of our history and development of our famous architecture.

You’ll be able to honestly respond “yes” when coworkers ask if you’ve seen all the tourist hotspots in downtown Chicago! Plus you will be able to then dazzle them with historical anecdotes and informed architectural observations. It’s an excellent introduction to Chicago for the more seasoned traveler. Because we do this highlights tour by bus, it works out great for any kind of weather.  

Get to know Chicago city tours
On the ground is one of the best ways to discover Chicago. Photo by Pawel Skrabacz.

2. Explore Architecture Inside Downtown Buildings

Chicago’s stunning skyline, glittering lake, gleaming glass-and-steel skyscrapers, and resourceful, eclectic look is only half the story of the Loop. While you may have seen Chicago architecture on an architectural boat cruise, the next step is to go inside the buildings on an interior architectural tour. Discover the stunning interiors–full of glittering mosaics, gleaming stained glass and hidden secrets on our Loop Interior Architecture Walking Tour. This private group tour starts in the heart of the Loop, walking distance from many of the new corporate headquarters. In addition to being a great private group event option, we also offer this city tour seven days a week as a public tour

P.S. Tour guests receive a printed map and introduction to the Pedway, the system of mostly underground passages that connect buildings downtown. 

3. Learn About the Booming Fulton Market

Google moved to the Fulton Market neighborhood in the West Loop in late 2015. McDonald’s has built a flashy new headquarters and are currently about to make their big move here, too. Tons of smaller and mid-size businesses are opening up in the former meatpacking district of Fulton Market. And we offer a private group tour here!

With so many people now working in Fulton Market, a little orientation to the history and architecture of the neighborhood through a walking tour. Our Factories to Calories Fulton Market Food Tour digs into the complex, evolving story of this neighborhood with meaty historical anecdotes about culinary and food processing history. You’ll glimpse the industrial past and corporate, foodie future while snacking on gourmet sandwiches and sipping local beer. Like our “Loop Interior Architecture Walking Tour,” this Fulton Market walking tour is also available to the public or as a private experience.

4. Get to Know Chicago Through its Neighborhoods

chicago neigborhoods architecture on private custom group tourChicago is a city of neighborhoods. They are where Chicagoans have created homes and identities for themselves. Several of our city tours go into various neighborhoods, of course. But we have two Chicago neighborhood tours that traverse a multitude of neighborhoods for private group clients. These private group tours will bring your group to explore the rich patchwork quilt of Chicago neighborhoods. They bring the city’s workaday existence and local culture to vivid life.

Our Cool Neighborhoods of Chicago Tour was made special for universities or companies wanting to orient or recruit. This tour ventures into neighborhoods popular for new Chicagoans and discusses new trends in city living. Neighborhoods include the Loop. Wicker Park and Fulton Market. 

For more historic background on the people that have made our city great, consider the Chicago Neighborhoods and Cultural Diversity Tour for your private group. This thoughtful Chicago neighborhoods tour explores immigration, industrialization, social change, segregation, and community. The bus drives through the varied Asian, European, and African-American communities that call Chicago home. 

Our private group tours accommodate groups as small as one guest or as large as 330 guests. If any of these private tour experiences sound right up your alley, or you’d just like to learn more, contact us here or give us a ring at (312)-350-1131.

– Morgan Lott, Private Tour Coordinator and Tour Guide


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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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