historic mansions of prairie avenue

The First Gold Coast. 
The Holiest of Holies of the Social Life of the City. 
The Sunny Street That Held the Sifted Few. 

The Prairie Avenue historic district has garnered many nicknames over the years, all relating back to a time just after the Great Fire of 1871—before the completion of Lake Shore Drive and the subdivision of North Astor Street—when the South Loop address attracted the city’s ultra-wealthy. Properties like the Clarke House, the city’s oldest surviving structure, and Glessner House, a masterwork whose threatened demolition in 1966 precipitated the creation of the Chicago Architecture Foundation, have helped to set the stage for historic preservation battles, and many successes, over the past 50 plus years. 

Since 1972, the district has been listed on the National Register of Historic Places, and became a designated Chicago Landmark in 1979. This excursion explores the many historic structures within the landmark district, which includes nine mansions, three row houses and the landmark, Gothic Revival Second Presbyterian Church, with an additional stop to take in the tranquil beauty of the Women’s Park and Gardens. As this is a residential neighborhood, please be respectful of people’s property and keep to the public right-of-way.

I’m Ronnie Frey creator of the popular Instagram account @doorwaysofchicago.  I welcome you to follow me there and all my other socials like TikTok, Facebook and YouTube with the same handle @doorwaysofchicago.  I also give in person tours and private tours and those can all be found on my website doorwaysofchicago.com.  If you would like to reach out my email address is ronnie@doorwaysofchicago.com and you can also join my email list using the form at the bottom of each page of the website.

Additionally, I would love to invite you to visit my website: doorwaysofchicago.com for other tour offerings including live, in-person tours and private tour offerings.  I also have all my eATLAS app tours listed with links to each one.  Once there you can read my story and see my offerings of photography prints, greeting card collections, and even my curated interior design furnishing collections.  I’m an interior designer by trade and during the pandemic, I started my Instagram account as well as these walking tours to be able to share more of my passions with you!

I’m constantly on the search for wonderful architectural content to share with you as well as anything vintage, especially planes, trains, and automobiles…after all, they all have doors too!

Thank you, and as I always like to say, “See you out on the trails!”



Second Presbyterian Church - NOTABLE PROPERTY

East Cullerton Street Rowhouses

Clarke House Museum

Glessner House Museum

Kimball House

Coleman-Ames House

Women's Park & Gardens - NOTABLE PROPERTY

Keith House

Marshall Field Jr. House

William Reid House

The Harriet F. Rees House

Wheeler Mansion

Discover The Fabulous Mansions Of The South Prairie Historic District - PLUS MORE!

Historic Mansions Of Prairie Avenue

the deep pockets of graceland cemetery

On this tour, you will see the tombs and mausoleums of many famous architects like William LeBaron Jenney, John Root, Louis Sullivan, Mies Van der Rohe, and Daniel Burnham, and other rich and famous "deep pockets" like Marshall Field, Palmer Potter, George Pullman, Walter Newberry and more!

Here in the app, I have included several additional photos related to some of the stops.  As you open each stop in the app I would suggest you read about the tomb first and then click on the two arrows in the upper right-hand corner of the first photo you see and that will pop out the photos and videos so you can view them full screen.  

Welcome to my THE DEEP POCKETS OF GRACELAND CEMETERY tour. I’m Ronnie Frey creator of the popular Instagram account @doorwaysofchicago.  I welcome you to follow me there and all my other socials like TikTok and YouTube with the same handle @doorwaysofchicago.  I also give in-person tours and private tours and those can all be found on my website doorwaysofchicago.com.  If you would like to reach out via email please feel free:  ronnie@doorwaysofchicago.com

I have designed a growing number of tours in this eATLAS app that span many different neighborhoods as well as downtown Chicago.  I welcome you to check them out!  Many of them have promo videos you can watch prior to purchasing. 

Graceland Cemetery History from Adam Selzer's Book: Graceland Cemetery, Chicago Stories, Symbols & Secrets (HIGHLY RECOMMEND!)

During Thomas Barbour Bryan's time in Chicago, there was hardly a week that he wasn't in the papers for something or another. An 1848 Harvard grad who spoke half a dozen languages, Bryan built railroads, erected concert halls, founded the suburb of Elmhurst, ran for mayor more than once, and rubbed elbows with the famous and infamous. 

The son of an abolitionist Virginia politician (and, by some accounts, a grand nephew of Daniel Boone), he served as a pallbearer for Abraham Lincoln,' and during the last months of the Civil War, he organized the Great Northwestern Sanitary Fair, which became a sort of victory lap for the just-won struggle. 

When General Grant made a speech at the fair—his first public speech Bryan introduced him onstage.

In the 1880s Bryan had an office in William Le Baron Jenney's Home Insurance Building, the first modern "steel frame" skyscraper. In the early 1890s, he was Vice President and Commissioner at Large for the World's Fair and Columbian Exposition, traveling the world and meeting with people such as the Pope to promote the interests of the upcoming Fair.

And in the middle of his Columbian Exposition work, he sold a 51 percent interest in a copier machine company to H. H. Holmes, the murderous "Devil in the White City," who paid him with a $7000 promissory note. Bryan never got a cent in cash, making him one of Holmes' biggest individual swindling victims.  He is probably the only person who knew both Abraham Lincoln and H. H. Holmes.
And, in the midst of all these exploits, he somehow made time to found Graceland Cemetery.



William LeBaron Jenney

Dexter Graves

John Root

Peter Schoenhofen

George Pullman

Ryerson Tomb

William Kimball

Louis Sullivan

William Goodman

Potter & Bertha Palmer

Charles Wacker

Daniel Burnham

Getty Tomb

Ludwig Mies van der Rohe

Ernie Banks

Richard Nickel

Cyrus McCormick

Marshall Field

Inez Clarke

Walter Newberry

Stroll through historical Graceland Cemetery and discover all the tombs of the rich and famous.

The Deep Pockets of Graceland Cemetery

workers cottages of old town triangle

"Chicago has faced its fair share of adversity in its 184-year history, but the city has always risen from the ashes, both literally and figuratively. Its most remarkable renaissance came in the wake of the Great Chicago Fire of 1871. The inferno killed 300 people, left another 100,000 homeless, and cost a jaw-dropping $222 million (equivalent to $4.7 billion in 2020), but it also gave birth to a beautiful new city, built with brick and better than ever. 

Sadly, one iconic building style, the workers cottage, which flourished both before and after the Great Fire, has recently been falling victim to urban developers whose visions just don’t jibe with historic lot sizes or bygone architectural styles. As demand grows for apartments and other higher-density housing, many of these humble dwellings are at risk of being razed."  -bobvila.com

On this tour you will see 40 or more of these delightful cottages and the different styles they were designed and constructed in. Also, you will see some very rare instances where there are several cottages in a row or in one case an entire block of cottages on both sides of the street! 

Stops called "NOTABLE PROPERTIES" are not worker cottages but historically notable for the neighborhood.

I’m Ronnie Frey creator of the popular Instagram account @doorwaysofchicago.  I welcome you to follow me there and all my other socials like TikTok, Facebook and YouTube with the same handle @doorwaysofchicago.  I also give in person tours and private tours and those can all be found on my website doorwaysofchicago.com.  If you would like to reach out my email address is ronnie@doorwaysofchicago.com and you can also join my email list using the form at the bottom of each page of the website.

Additionally, I would love to invite you to visit my website: doorwaysofchicago.com for other tour offerings including live, in-person tours and private tour offerings.  I also have all my eATLAS app tours listed with links to each one.  Once there you can read my story and see my offerings of photography prints, greeting card collections, and even my curated interior design furnishing collections.  I’m an interior designer by trade and during the pandemic, I started my Instagram account as well as these walking tours to be able to share more of my passions with you!

I’m constantly on the search for wonderful architectural content to share with you as well as anything vintage, especially planes, trains, and automobiles…after all, they all have doors too!

Thank you, and as I always like to say, “See you out on the trails!”


Rowhouses by architect Harold Hansen

215 W Eugenie - Matthew Buschwah Cottage 

217 West Eugenie Street

219 West Eugenie Street

225 West Eugenie Street 

Home of Henry Gerber

319 West Eugenie St - PETER JUNG RESIDENCE 

405-07 West Eugenie - O'CONNELL RESIDENCE 

SAINT MICHAEL'S CHURCH 

Twin Anchors Ribs 

335 West Concord Place 

329 West Concord Pl - HEINRICH FISHER RESIDENCE 

316 W. Concord Place

310 W. Concord Place

306 W. Concord Place

305 West Concord Pl - NICHOLAS BIRREN RESIDENCE 

1638 N. North Park - Workers Cottage

1722 N. North Park - Elaborate, Italianate Workers Cottage

331 West Menomonee St - THEODORE BECKING RESIDENCE 

1824 North Orleans St - JAMES ROTTRAY RESIDENCE 

1819 North Orleans Street

NOTABLE PROPERTY - 1827 North Orleans St - JOHN W. WHITE RESIDENCE 

FREDERICK WACKER RESIDENCE 1838 North Lincoln Park W. 

CHARLES WACKER HOUSE 1836 North Lincoln Park West 

Ann Halsted Rowhouses

Large Italianate Farmhouse 1802 N. Lincoln Park W

NOTABLE PROPERTY - 226 West Menomonee Street

FIRE RELIEF SHANTY. 216 West Menomonee St 

See 30+ Stunning Chicago's Workers Cottages - An Architectural Vernacular Of the Late 1800's - PLUS OTHER NOTABLE PROPERTIES

Workers Cottages Of Old Town Triangle

match.com inside chicago fine arts building tour april 13, 2024

Nestled in the vibrant cultural landscape of downtown Chicago, the Fine Arts Building, an architectural gem, has stood as a testament to creativity and craftsmanship since its inception in 1898.

As you traverse the ornate corridors, walk up and down the grand staircase, and ride some of the last manually operated elevators in the city, you'll be transported back in time to an era when the arts flourished. The Fine Arts Building, originally built in 1887, housed the Studebaker Carriage Company’s showroom and factory.

This guided tour will unravel the stories embedded in the building's exquisite architecture, highlighting its role in fostering creativity. Explore the floors that once housed studios of influential artists, musicians, and writers, immersing yourself in the same spaces that inspired the likes of Frank Lloyd Wright, Lorado Taft, and Sherwood Anderson.

Every corner of the Fine Arts Building whispers tales of the creative and enduring spirit of Chicago's artistic heritage. Designed by Solon S. Beman, the architect behind the Pullman Palace Car Company, the building served as a hub for Chicago's burgeoning arts scene in the late 19th century. Now, 125 years later, it continues to play the same pivotal role, preserving the old and perpetuating a new and exciting artistic colony within its historic walls.

Exterior Details 

Lobby and First Floor Corridor

Studebaker Theatre

2nd Floor Gallery

Elevator Circus Ride

926 Solon Spencer Beman

1025 Leyendecker Brothers

1024 Ralph Seymour

1038 Lorado Taft

1020 Frank Lloyd Wright

1014 Ralph Clarkson and The Little Room

10th Floor Murals

800 Cordon Club and Nellie Walker

825 Anna Morgan

410 The Harrington Institute Of Interior Design

4th Floor Venetian Court

424 Fab Finds by Doorways Of Chicago

Step into the heart of Chicago's enchanting artist’s colony with this tour inside the Fine Arts Building.

Match.com Inside Chicago Fine Arts Building Tour April 13, 2024

retro river north

Hi and welcome.  I’m Ronnie Frey creator of the popular Instagram account @doorwaysofchicago.  I welcome you to follow me there and all my other socials like TikTok, Facebook and YouTube with the same handle @doorwaysofchicago.  I also give in person tours and private tours and those can all be found on my website doorwaysofchicago.com.  If you would like to reach out via email please feel free:  ronnie@doorwaysofchicago.com.

I’m constantly on the search for wonderful architectural content to share with you as well as anything vintage, especially planes, trains, and automobiles…after all, they all have doors too!

Speaking of things vintage, welcome to my RETRO RIVER NORTH walking tour where you will get to see several establishments and their amazing vintage signs and vintage neon signs.  Plus along the way I will show and tell you all about many notable properties like I always do.  It’s hard to walk past a historical place and not include it on the tour - even though these other properties may or may not have a vintage sign they are still just as much a part of Chicago’s history.

I will give you a clue, the best time to take this tour is in the evening as the sun is setting or at dusk as you will be able to see most of the lights illuminated!  

Also for your convenience, I have included several photos related to many of the stops including some interior photos and a short video message about each stop.  You can either read the information in the app or if you’d rather, just listen to my video.  As you open each stop in the app I would suggest that you click the icon in the upper right-hand corner of the first photo you see and that will pop out the photos and videos so you can view them full-screen.  

Enjoy the tour!  If you are going in the evening, the last stop is at the Tortoise Supper Club and you may want to stop in to hear their live jazz -  the musicians start at 7:30 or 8 pm - it's a great way to end the tour!

Additionally, I would love to invite you to visit my website: doorwaysofchicago.com for other tour offerings including live, in-person tours and private tour offerings.  I also have all my eATLAS app tours listed with links to each one.  Once there you can read my story and see my offerings of photography prints, greeting card collections, and even my curated interior design furnishing collections.  I’m an interior designer by trade and during the pandemic, I started my Instagram account as well as these walking tours to be able to share more of my passions with you! 

If you would like to reach out my email address is ronnie@doorwaysofchicago.com and you can also join my email list using the form at the bottom of each page of the website.

Thank you, and as I always like to say, “See you out on the trails!”


LaSalle Flowers

Rowhouse - 154 W. Superior


Clark Street Ale House

Rosebud On Rush

St. James Cathedral

Cable House

Driehaus Museum

The Murphy

McCormick Double House

Pizzaria Due

Medinah Temple

Uno Pizzaria & Grill

Freehand Hostel

Tree Studios

P.O.S.H.

Redhead Piano Bar

Chicago Chop House

Hard Rock Cafe

Harry Caray's Italian Steak House

House Of Blues

Tortoise Supper Club

Retro River North

chicago art deco madness part i

Art Deco, sometimes referred to as Deco, is a style of visual arts, architecture and design that first appeared in France just before World War I. It influenced the design of buildings, furniture, jewelry, fashion, cars, cinemas, trains, ocean liners, and everyday objects such as radios and vacuum cleaners.  It took its name, short for Arts Décoratifs, from the Exposition Internationale des arts décoratifs et industriels modernes (International Exhibition of Modern Decorative and Industrial Arts) held in Paris in 1925.

You will see many clean-lined and simple, "moderne" motifs of the deco period on this tour which include: streamlined shapes, horizontal lines (suggesting speed), verticality in buildings, zig zags or ziggurats, stair-stepping, sunbursts, silver and golden metallics, and a general sense of modern style & glamour of the roaring twenties and flapper eras.

Art Deco combined modern styles with fine craftsmanship and rich materials. During its heyday, it represented luxury, glamour, exuberance, and faith in social and technological progress.

I’m Ronnie Frey creator of the popular Instagram account @doorwaysofchicago.  I welcome you to follow me there and all my other socials like TikTok, Facebook and YouTube with the same handle @doorwaysofchicago.  I also give in person tours and private tours and those can all be found on my website doorwaysofchicago.com.  If you would like to reach out via email please feel free:  ronnie@doorwaysofchicago.com

I have designed a growing number of tours in this eATLAS app that span many different neighborhoods as well as downtown Chicago.  I welcome you to check them out!  Many of them have promo videos you can watch prior to purchasing.

Chicago Board Of Trade 

Bank Of America Building (Field Bldg)

One North LaSalle Building

Thirty Thr33 N. LaSalle

Chapel In The Sky - 1st United Methodist Church

Spirit of Electricity - God Of Lightning Scuplture

Franklin Savings Bank - 105 W. Madison 

Silversmith Hotel

Marshall Field Store Elevator Doors and Escalators (Inside Macy's)

333 N. Michigan Avenue

Carbide & Carbon Building - Pendry Hotel

Chicago Motor Club Building

Discover Art Deco architectural treasures in Chicago's Loop

Chicago Art Deco Madness Part I

historic homes, cottages & buildings of wicker park

Chicago has faced its fair share of adversity in its 185-year history, but the city has always risen from the ashes, both literally and figuratively. Its most remarkable renaissance came in the wake of the Great Chicago Fire of 1871. The inferno killed 300 people, left another 100,000 homeless, and cost a jaw-dropping $222 million (equivalent to $4.7 billion in 2020), but it also gave birth to a beautiful new city, built with brick and better than ever. 

"Sadly, one iconic building style, the workers cottage, which flourished both before and after the Great Fire, has recently been falling victim to urban developers whose visions just don’t jibe with historic lot sizes or bygone architectural styles. As demand grows for apartments and other higher-density housing, many of these humble dwellings are at risk of being razed."  - Bob Vila

On this tour, you will see 40-50 of these delightful cottages and the different styles they were designed and constructed in. In addition, you will see and learn the history of at least 25-30 other stunning and historically significant homes, mansions and buildings in the charming neighborhood of Wicker Park.

I’m Ronnie Frey creator of the popular Instagram account @doorwaysofchicago.  I welcome you to follow me there and all my other socials like TikTok, Facebook and YouTube with the same handle @doorwaysofchicago.  I also give in person tours and private tours and those can all be found on my website doorwaysofchicago.com.  If you would like to reach out via email please feel free:  ronnie@doorwaysofchicago.com

I have designed a growing number of tours in this eATLAS app that span many different neighborhoods as well as downtown Chicago.  I welcome you to check them out!  Many of them have promo videos you can watch prior to purchasing.

1236 N. Hoyne - Workers Cottage

1301 N. Hoyne Apartment Building

1311 N. Hoyne - Workers Cottage

1317 N. Hoyne - Workers Cottage

1343 N. Hoyne - Georgian Residence

1345 N. Hoyne - Second Empire Residence

1400 N. Hoyne - Giant Workers Cottage

1407 N. Hoyne - Second Empire Mansion

1417 N. Hoyne - Italianate Residence

1427 N. Hoyne - Romanesque Revival Residence

1426 N. Hoyne - Tiny Workers Cottage

Wicker Park Lutheran Church

2128 W. Le Moyne - Workers Cottage

2131 W. Le Moyne - Workers Cottage and Sausage Factory

2137 W. Pierce - High Late Victorian Era Residence

1520 N. Hoyne - Second Empire Residence

1521 N. Hoyne - Queen Anne Residence

1558 N. Hoyne - Modified Queen Anne Residence

2039 W. North - Turkish Baths 

2108 W. North - The Robey Hotel

1420 N. Wood - Fly Boy and Lil Mama

1395 N. Milwaukee - Workers Cottage Parklet Sculpture

1338 N Wicker Park Ave - Queen Anne Residence

1348 N. Wolcott Ave - Workers Cottage

1270 N. Wolcott Ave - Second Empire Workers Cottage

1266 N. Wolcott Ave - Workers Cottage

 1958 W Evergreen Ave Nelson Algren's Home

See 40+ Stunning Wicker Park Workers Cottages - An Architectural Vernacular Of the Late 1800's - Plus 25+ other notable historic homes, mansions and buildings.


Historic Homes, Cottages & Buildings Of Wicker Park

pullman national historical park

Discover the crossroads of American history that is uniquely Chicago.  This is the most fabulous, MUST-SEE, historic preservation project in all of Chicago! The new National Park Service Pullman Visitor Center is located in the former Administration Clock Tower Building of the Pullman Palace Car Company Factory. A 141-year-old piece of history that is making history again as the first National Monument in America located in an urban setting!

Pullman was the first model, planned industrial community in the United States. The district is significant for its historical origins as one of the most famous company towns in America and scene of the violent 1894 Pullman strike. 

It is a story of American opportunity.

I’m Ronnie Frey creator of the popular Instagram account @doorwaysofchicago.  I welcome you to follow me there and all my other socials like TikTok, Facebook and YouTube with the same handle @doorwaysofchicago.  I also give in person tours and private tours and those can all be found on my website doorwaysofchicago.com.  If you would like to reach out via email please feel free:  ronnie@doorwaysofchicago.com

I have designed a growing number of tours in this eATLAS app that span many different neighborhoods as well as downtown Chicago.  I welcome you to check them out!  Many of them have promo videos you can watch prior to purchasing


111th Street Metra Station Murals

NPS Pullman National Monument Visitors Center

Hotel Florence

Arcade Park

Historic Pullman Exhibit Hall

Visions Of Pullman Mural - 1996

Pullman Livery Stables

George Pullman Elementary School 1907

Honeymoon Row

Florence Lowden Miller Center

Market Hall & Colonnade Apartments

Greenstone Church

Arcade Row - Jr. Executive Housing

Pullman House Project...At Home in Pullman

Executive Housing

Gateway Park

Block Houses A & C

Pullman Artspace Lofts 

Pullman National Historical Park

bits of boystown 

Home to one of the largest LGBT communities in the Midwestern U.S., Boystown is a bustling neighborhood in West Lakeview. It has hosted Chicago’s annual Pride Parade since 1971 with over 1 million people attending each year!  The neighborhood has charming coffee shops, cool record stores and trendy boutiques along its tree-lined streets. Known for its comedy clubs and offbeat theaters, the area also draws young, hip crowds to its vibrant cocktail bars and nightclubs.

I’m Ronnie Frey creator of the popular Instagram account @doorwaysofchicago.  I welcome you to follow me there and all my other socials like TikTok, Facebook and YouTube with the same handle @doorwaysofchicago.  I also give in person tours and private tours and those can all be found on my website doorwaysofchicago.com.  If you would like to reach out via email please feel free:  ronnie@doorwaysofchicago.com

I have designed a growing number of tours in this eATLAS app that span many different neighborhoods as well as downtown Chicago.  I welcome you to check them out!  Many of them have promo videos you can watch prior to purchasing

Space Park - Roscoe Garden Park

Roscoe's Tavern

Legacy Walk Pylons & Rainbow Crosswalks

Hydrate Nightclub

Center On Halsted

Kit Kat Lounge & Supper Club

Cell Block

The North End

Bobby Loves

Fantasy Night Club

Little Jims

Replay Beer & Bourbon

Progress Bar

Sidetrack

See all the hot spots of Boystown and learn about some fascinating history of the area.

Bits Of Boystown 

Ronnie Frey @doorwaysofchicago

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