Prairie Avenue Chicago: The City’s First Neighborhood of Mansions

Maybe you’ve heard of the elite Gold Coast neighborhood on the Near North Side, but how about the Historic District of Prairie Avenue? Potter Palmer constructed a million-dollar mansion on the formerly-swampy Lake Shore Drive in 1882, establishing the city’s most affluent neighborhood on the North Side. Still, it wasn’t Chicago’s first affluent neighborhood. Before the Gold Coast, there was “Millionaire’s Row,” an even denser cluster of mansions belonging to Chicago’s most prosperous people between the 1600 to 2200 blocks of Prairie Avenue on the Near South Side.

We research Chicago history and architecture like this while developing our live virtual events and custom corporate events. Join us for our public virtual events or book an exclusive team-building event for your private group. We can also create custom tours and original content creation about this Chicago topic and countless others.

Prairie Avenue historic photo mansions
Prairie Avenue in its Gilded Age heyday.

Prairie Avenue was Millionaire’s Row

Prairie Avenue mansion illustration
A drawing of the grand Gilded Age mansions which stretched up and down Prairie Avenue.

Like many of Chicago’s main streets, Prairie Avenue evolved from a Native American trail that connected Chicago’s Fort Dearborn with Indiana’s Fort Wayne. The area became a desirable location because of its proximity to downtown business without the hassle of crossing the Chicago River. Things really flourished after the Great Fire of 1871. Prairie Avenue and its immediate surroundings were untouched, while the North Side was torched. Displaced people and businesses who could afford it relocated to the south of the Loop.

Prairie Avenue Kimball Mansion
The Kimball House, which today houses the U.S. Soccer Federation.

The Who’s Who of Chicago

Prairie Avenue was home to the men who made Chicago a global city. It featured the crème de la crème of Chicago gentry and architecture. To name a few highlights of this exclusive and close knit community:

  • Marshall Field’s mansion was designed by Richard Morris Hunt (architect of the Vanderbilts’ “The Breakers” in Newport, Rhode Island).
  • Daniel Burnham designed the home of John B. Sherman, one of the founders of the Union Stock Yard. Burnham met and then married Sherman’s daughter as a result of this commission. Down the line, he eventually lived in the mansion he’d designed.
  • George Pullman enlisted Solon S. Beman to design his Prairie Avenue home after Beman designed the entire layout of his company town, “Pullman. ” Beman was also architect for Marshall Field Jr.’s 43-room, 30,000-square-foot home (that is now six condos) as well as W.W. Kimball’s (of piano and organ fame) home.
  • Henry Ives Cobb, designer of the Newberry Library and many University of Chicago collegiate gothic buildings, designed two homes that are actually still standing today. Incredibly, his Rees House was hoisted up and moved down the street to make way for McCormick Place’s expansion in 2014.

End of an Era

Pollution and noise from nearby train yards, as well as encroaching districts of industry and “undesirable” activities eventually made Prairie Avenue and its Near South neighborhood less appealing to the wealthy leaders of Chicago. Palmer’s new setup in the Gold Coast also drew the aristocratic class to the North Side. Over the decades, factories, parking lots, and warehouses replaced the grand mansions. Only seven of these mansions still exist today. Only a heroic preservation effort saved them all from demolition. A small group of preservation-minded people, which eventually became the Chicago Architecture Foundation, saved H.H. Richardson’s Romanesque Glessner House from the wrecking ball in 1966.

Visit the Museums of Prairie Avenue

Clarke House Chicago oldest building
The Clarke House is the oldest building constructed in the city of Chicago. Photo via Wikimedia.

I learned about this forgotten neighborhood when I interned for the Glessner and Clarke House Museums this past spring. The museums, along with the Prairie District Neighborhood Alliance have worked very hard in revitalizing the area and educating the public with their own house tours and an annual neighborhood tour to see historic home interiors. On our “Century of Contrasts South Loop Walking Tour,” we would step into the ornate rooms of this Gilded Age Mansion. We can still create a custom private tour that takes you there, of course.

Glessner House Main Hall interior Prairie Avenue
The eye-popping Main Hall of the Glessner House. Photo by by James Caulfield; courtesy of Glessner House.

The Glessner House courtyard as well as Women’s Park are available for schmancy weddings, corporate events, and banquets. The historic Wheeler Mansion, down the block from Glessner, has been beautifully restored. Today, it’s a boutique hotel and hosts a lively farmer’s market in the summer. Glessner House also often hosts special tours and presentations on history. The gorgeous Second Presbyterian Church, the favored church of Chicago’s Gilded Age gentry, offers guided tours of its 1874 architecture, including a stunning Arts and Crafts style renovation and painterly stained glass masterpieces. There’s lots to do to explore the up-and-coming Near South Side neighborhood, where the glamorous past is coming into clear view again.

— Marianna Foral, Research Intern


In business since 2010, Chicago Detours is a passionate team of educators, historians and storytellers. We applied a decade of experience as one of Chicago’s top-rated tour companies to become a virtual event company in 2020. We bring curious people to explore, learn and interact about Chicago’s history, architecture and culture through custom tours, content production, and virtual events.


Share on facebook
Share on twitter
Share on pinterest
Share on linkedin

be a



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

Book a chicago event

Let’s Connect!