Last Updated on September 20, 2022 by JaimeSays
It’s only been in the last few years that I’ve started taking tours in Chicago, the city I’ve called home for over ten years. The Chicago architecture tours are unbelievably interesting. I’ve gone on many a Chicago walking tour, rain or shine. With inclement weather and other obligations, sometimes paying the $15-$20 for a Chicago walking tour doesn’t seem like a great idea. What if you could go on a Chicago walking tour self guided? That’s right, I’m talking about a self guided Chicago walking tour. I’m an architecture gal, but if street art is your thing, check out this Chicago mural tour. With a self guided Chicago architecture tour, you are able to go whenever you want to and move at your own pace. If you planned to go one weekend but then it was too rainy or too hot, you can go another time. Our first stop is in the South Loop, Chicago in the historic Prairie District.
The History of Prairie Avenue
Prairie Avenue was the it street of Chicago in the late 1800s. After the Great Chicago Fire of 1871, many of the cities most influential families moved to Prairie Avenue and built grand stone homes. After the city outlawed the building of timber homes after the fire, these beautiful mansions were much more fireproof then their wooden predecessors. The most elaborate homes were built in a six block stretch, from 16th Street to the North and 22nd (Cermak) to the south. Today, Prairie District from 16th Street to 18th Street is high rises and new townhomes. As such, today’s self guided Chicago walking tour will focus on the area from 18th Street south to Cermak.
Self Guided Chicago Walking Tour Logistics
Where: Prairie Avenue, from 18th Street to Cermak Avenue, in Chicago
How Long: This self guided Chicago walking tour is 0.33 miles down Prairie Street, with a final stop on Cullerton. Down and back is just about 2/3 of a mile long. You can easily do this walking tour in thirty minutes, and then stop at Woven and Bound at the Marriott Marquis to treat yourself to a delicious meal.
When: Whenever! This is a Chicago walking tour, self guided for you to go whenever you are available.
1800 South Prairie: The Glessner House Museum

The Building
Located at the Southwest corner of 18th Street and Prairie Avenue, the Glessner House Museum is a heavy stone structure that looks more like a castle than a family home. It isn’t until you take a peek around the corner on 18th however, that you see that this building is actually a palatial fortress. At 17,000 square feet, this home is an H.H. Richardson design completed in 1887. Its exterior is made of dolomite from other parts of Illinois. Much of its design had practical implications ahead of its time. Just like Frank Lloyd Wright after him, H.H. Richardson built an interior in the Arts and Crafts style with an integrated environment. While looking medieval from the outside, the inside was decidedly modern. Nearly every room had its own fireplace for heat and the entire house had electricity and lighting before 1893’s World Fair.
The People
The Glessners commissioned the house after a move to Chicago from Ohio. John Glessner made his fortune as partner in a firm that sold farming equipment. They family owned the house off and on for nearly 60 years and the house was finally placed on the National Historic Register in 1970. It became a museum in 1994.
Today
Saved from demolition in 1966, today the Glessner House is a Museum. Tours are 11:30AM, 1PM, and 2:30PM Wednesday through Sunday, with free admission on Wednesdays. Otherwise, tickets are $15 for adults.
1801 S. Prairie Avenue: William W. Kimball House

The Building
Next up on the self guided Chicago walking tour: the Kimball house. This Chateauesque home was the home of William W. Kimball, founder of the Kimball Piano and Organ Company. Although its interior is organized like a simple rectangle, the ornateness of the exterior provides all the pizzazz of the building. A highly sloped roof, conical turrets, and elaborate gables decorate the building. Completed in 1892, its limestone exterior and richly decorated interior still reflect the richness of the home.
The People
William W. Kimball founded the Kimball Piano and Organ company in 1857 on the South Side of Chicago. After losing all of his inventory due to the Great Chicago Fire of 1871, he spent a short period of time selling and manufacturing pianos from his home. Mr. And Mrs. Kimball were avid art collectors. Upon their deaths, they bequeathed their collection of works to the Art Institute of Chicago.
Today
Today, the William W. Kimball mansion houses the U.S. Soccer Federation headquarters. An addition made at the end of the twentieth century linked the Kimball house with the Coleman house as the soccer federation needed more space.
Worked up an appetite? Try some sushi or one of Chicago’s date night restaurants!
1801 South Indiana: The Clarke House at Chicago Women’s Park and Garden
The next stop on the self guided Chicago walking tour in the Sotuh Loop technically has an address on Indiana Avenue, but it sprawls all the way to Prairie Avenue. It is next door to the Glessner House so you can’t miss it.

The Building
The grounds of Chicago Women’s Park and Garden encompass the entire west side of the 1800 block of Prairie Avenue. The green space and community gardens are beautiful and well kempt. Sitting smack dab in the middle of the park is Chicago’s oldest home. The Clarke House was built in 1836, a year before Chicago was officially incorporated as a city. Built in the Greek revival style of architecture, original location of the home was just about 1700 South Michigan.
After the surviving the Great Chicago Fire of 1871, the house was moved 28 blocks south, away from the hubbub of the city. When the house was deemed too large for an individual family, it was purchased by St. Paul Church of God in Christ. By 1977, the city of Chicago purchased the property. The city relocated the house nearer to its original location in the South Loop where it sits today.
The People
The Clarkes came to Chicago from Utica, New York. With the promise of wealth and opportunity as their guide, merchant Henry became a partner in a hardware firm. With the major population boom in the prairie land of Illinois, hardware was needed for new construction throughout the area. When the home was built, it was built among tall prairie grass and its entrance was a footpath right off of Lake Shore Drive. After the panic of 1839, the Clarkes turned to farming on their land. Henry Clarke died early due to a cholera outbreak that wiped out nearly one third of Chicago’s population. His wife died just a few years later. The Clarke children kept the house in the family until 1872 when they sold it to the Grimes family.
Today
The Clarke House is a museum located within the Women’s Park and Garden. While it used to cost a fee to enter the home, tours are now free. Tours are approximately one hour long and occur on Wednesdays, Fridays, and Saturdays at 1PM and at 2:30 PM. There is a 15 person limit per tour.
1900 South Prairie Ave: The Elbridge G. Keith House
The next stop on your self guided Chicago walking tour has a celebrity connection. Have you ever watched the Showtime program, Shameless? At the end of season seven, the character of Lip checks into rehab. This is the home that portrayed the rehab facility in the show, and with so much character, you can understand why the director had to include it.
The Building
The Keith House is designed in a typical Victorian Chateauesque style, combining classical French styling with that of traditional English. Completed in 1870, the home is the work of J.R. Roberts. At over 10,600 square feet and seven bedrooms, this house was built for Elbridge Keith. The third floor mansard roof was an addition in the 1880s. Elbridge Keith’s widow sold the house in 1920, and afterward, the home served a commercial purpose as a publishing company and book store. Notice the white posts in front of the stairs. These posts were used to tie up horses. See the holes in the posts? That’s where you slipped the rope through to make sure your horse didn’t get away.
The People
One of three Keith brothers that all lived on this toney block of Prairie Avenue, Elbridge Keith made his fortune in millinery, banking, and the mortgage industries. He founded First National Bank and was very active in public service. He was a director of the World’s Columbian Exposition, and treasurer of the University of Illinois. Keith also helped to create and serve as president of the Union League Club, and served as treasurer of the Moody Bible Institute. He and his wife Harriet had six children, whom they raised in the family home on Prairie Avenue.
Today
In 1978, the Pratt family purchased the home and have since used the property as their home as well as an event space and art gallery. It was most recently listed for sale at a cool three million dollars.
1919 South Prairie: The Home and Deathbed of Marshall Field Jr.

Marshall Field changed the way people shopped. With his gorgeous department stores and exceptional customer service, he quickly became a mogul in Chicago. While his home was located at 1905 South Prairie, his son moved one door down, into a home provided by his father at 1919 South Prairie.
The Building
The Marshall Field Jr. mansion was built in 1884 by Spencer Solon Beman. Marshall Field Sr. bought it for his son in 1890. Once purchased by Field, the magnate brought on Chicago darling Daniel Burnham to make additions bringing the total size of the building to over 30,000 square feet. Beman is best known for his work designing the Pullman neighborhood for employees of the Pullman Palace Car Company. Built of red brick and local sandstone, the Queen Anne style mansion was a standout, even on a block known for its mansions
The People
Marshall Field Sr. purchased the home in 1890, and immediately hired Daniel Burnham to add on to the building. Marshall Field founded the department store of the same name that was the jewel of Chicago shopping. The home was a wedding gift for his son Marshall Field Jr.. Known for their opulent parties, the Fields were very popular in the area. Known as a frequent visitor to the Everleigh Club brothel located on 21st (now, Cullerton) and Dearborn, history tells us that Marshall Field Jr. fell victim to a gunshot wound at the brothel but was carried to his home in order to prevent scandal. He succumbed from his wound on November 22, 1905. The building spent much of the 70 years between 1923 and 1993 boarded up and abandoned, until a residential development company restored it.
Today
Today the mansion is made up of six condos, with price ranges between $770,000 and $1.7 Million. Some of the 30,000 square feet was lost due to garage space, but owners of the units have access to a gorgeous courtyard with topiary and benches.
If you like learning about architecture, consider a short getaway to Columbus, Indiana. This mecca of Modernist architecture is worth at least a day trip. These are my must see things to do in Columbus, Indiana.
2013 South Prairie Avenue: The William H. Reid House
The Building
This Classic Revival style building is the last remaining residential building in a row of attached houses previously extended the length of the block. Completed in 1894, this home is the first residence in Chicago built with steel frame construction. It is the first fireproof home of the city, with floors of poured concrete. The off-center entrance opens into a stunning performing room. With a platformed stage and under an interior Healy and Millet stained glass dome, a sun tube runs all three floors of the house providing natural light throughout. It was built by the firm Beers, Clay, and Dutton. Much of the interior has remained original, including the nine fireplaces.
The People
William H. Reid, a successful banker, built this home for his second wife. She was an avid singer and loved to entertain. The main floor performing area was the jewel of this home.
Today
The National Register of Historic Places added the William H. Reid home to its register in 2003. Today, it is owned and inhabited by Isberian Rug company owner, Oscar Tatosian.
2017 South Prairie Ave: The Harriet F. Rees House
The Building
This Romanesque style row house is an 1888 beauty designed by the firm of Cobb & Frost. Originally located at 2110 S. Prairie, the building was moved in November 2014 to make way for the Wintrust Arena. The interior features ornately carved wood, mosaic fireplaces, and numerous built in cabinetry.
The People
The widow of a prominent and successful real estate mogul and land surveyor, Harriet Rees died within a few years of moving into the house. It was then purchased by one Edson Keith Jr., one of three Keith brothers to live on Prairie Avenue. His daughter Katherine, who grew up in this home, went on to marry famed Chicago architect, David Adler of the Adler Planetarium.
Today:
The building last changed hands in the 2000s. It is currently owner occupied by a private family.
213 East Cullerton Street: Dr. Charles W. Purdy House
The Building
This building was one of three nearly identical homes built at 213, 215, and 217 E. Cullerton Street. 215 is the only one no longer standing. Built by the same architecture firm of Thomas & Rapp, 213 was commissioned in 1891 and 217 in 1892. Each floor of the homes feature different style windows, and the cornice is highly decorated with brackets, egg-and-dart-trim, and dentil moulding.
The People
Dr. Charles Purdy, the house physician for the Auditorium Hotel, moved to Chicago from Canada in 1871. He is known as the first physician who opened a clinic in the burned zone of the city. Dr. Purdy had this home built in 1891, after marrying Miss Florence Hoffman of Oak Park, IL. His work in urology and diabetes research is well known.
Today:
The current owner of 213 E. Cullerton is working on restoring the interior to the building’s former glory.
I hope you have enjoyed this walking tour!
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your story of 2013 prairie should tell of the espenshades, who lived in the home durung the war years, 1940’s. they moved there from 50th and lake park ave. they went often to mrs’s home area in indiana, just off hwy 41, for the day. Mrs morelli and her son lived at 213 cullerton, he was active in many activities in 1st ward. owned some property, some pretty notorious. the gibsons lived at 217 cullerton, the father had been a photographer. jesse, who liked to invent, was married to florence, who finally had to part with the properties at 213, 215 and 217. sad story she just ran out of money and steam. she befrended a postal worker. 2011 prairie was t. j. murphy, he needed a garage and vacant lots nearby for scavanger trucks. the espenshades were the last family that i know of to remain on that part of prairie avenue.
Oh I had no idea. It sounds like you knew them! That’s a good tidbit of history you’ve got there. Did/do you live in the area?
What do you mean 215e Cullerton is no longer standing?
The original building at that address is no longer standing. A newer building stands in its place.