Historic Homes, Cottages & Buildings Of Wicker Park: Ronnie
Brief History Of Wicker Park
Wicker Park feels frozen in time.
Packed with Victorian homes—cottages to mansions.
Settled by Germans and Scandinavians, rich and poor.
On the tour you’ll see stained glass, carved doors, gazebos, and gingerbread porches.
In 1871, it was still open prairie.
Great Fire did 2 things:
- Acted as a catalyst for the settlement of this area.
- Created a merchant class for those in the lumber & building trades.
Pyrophobia – Homes were brick and stone with metal details—no more wood.
Wealthy Germans left ghetto of Old Town but were scorned by S. Prairie Avenue elites.
Many showed off their wealth by building here.
- Chicago’s first horse-drawn streetcar ran from North & Milwaukee to downtown.
- These horse-drawn taxis were called “hacks.”
- Described as bumpy rides, long trips, and trouble with kids.
Photo 1 – Horsedrawn Hacks
U.S. Labor History
Besides architecture, Wicker Park is also important in U.S. Labor history.
After the Fire, times were hard for this new immigrant working class.
- Worked 10 to 12 hours days
- Contractors would often neglect to pay them
- Protests and riots occurred in the name of an 8-hour workday
Photo 2 – Poster For 8-Hour Workday
German workers and the new American Federation of Labor declared May 1, 1886, a day of protest for the Eight Hour Day Movement.
A full week of demonstrations followed.
At the end: The Haymarket Protest Meeting
The crowd had started to disperse when police arrived.
A riot broke out—someone threw dynamite.
Photo 3 – Haymarket Riot
The Pullman Strike began on May 11, 1894—just 8 years later.
It lasted two months and disrupted rail traffic nationwide.
The federal government sent in 4,000 troops to stop it.
Violence broke out—many were killed and property was destroyed.
Labor Day was created in response to this unrest.
Photo 4 – Pullman Strike Destruction
Photo 5 – Pullman Strike Destruction
Photo 6 – First Labor Day Parade Poster
History Of Workers Cottages
Chicago’s Rapid Growth
- 1837: Population ~4,000
- 1850: 30,000
- 1871 (Great Fire): 300,000
- Fire killed 300, left 100,000 homeless
- 1900: 1.2 million
- Today: 2.7 million
Why the Boom?
- Industrial Revolution
- Railroads + telegraph
- Central location + Lake Michigan
- Key industries: meatpacking, grain, rail cars
- Pullman Co. brought in workers and porters
Workers Cottages Rise
- Built fast and cheap for booming population
- Raised first floors, lower units rented out
- $100 down, $10/month (furnished!)
- Came in many shapes and sizes
What’s Happening Now
- Many cottages are at risk
- Small lots + old styles don’t fit modern builds
- Getting torn down for dense development
Photo 7 – What Chicago looked like around 1870.
Photo 8 – Brick Cottage Advertisement
Photo 9 – Wood Cottage Advertisement
1236 N. Hoyne
Brick Workers Cottage
Style: Italianate
Built: 1886
Features:
Double brackets in the eaves
Dentil molding in the eaves
Beautiful arched and carved terracotta lintels over doors and windows with scroll designs at both ends
1311 N. Hoyne
- 1311 N. Hoyne – Brick Workers Cottage
- Style: Italianate
- Circa: 1887
- Features:
- -Projected bay window
- -Original stained glass
- -Original cast-iron railings
- -Fancy, carved wave-shaped and dentil molding in the eaves
- -Small, Eastlake (Gingerbread)-style covered porch with very detailed latticework and turned columns
Photo 10 – Charles Eastlake Book
“Eastlake” is synonymous with “Gingerbread” and “Stick Style”
1345 N. Hoyne – Dr. Karl Sandberg
- Style: French Second Empire / Romanesque
- Second Empire – Think The Addams Family Home
- Romanesque – Think Game Of Thrones
- Circa: 1895
- Sandberg was a prominent surgeon, gynecologist, and professor
The Second Emporer of France (Napolean III) commissioned a man named Baron Haussmann for the renovation of Paris. It was a vast public works programme between 1853 and 1870. The medieval neighbourhoods were overcrowded and unhealthy. The renovation included:
-the building of wide avenues
-new parks and squares
-new sewers, fountains, and aqueducts.
-the street plan and distinctive appearance of the center of Paris today are largely the result of Haussmann’s renovation, this new Second Empire style was born and its influences spanned the globe.
Photo 11 – French Second Empire Home In St. Louis – reminiscent of the Addams Family Home
1407 N. Hoyne – John Raap
- Style: Second Empire / Italianate
- Circa: 1879
John H. Raap, a wealthy wine merchant.
Includes a matching coach house and original fence.
Raap was murdered by his bookkeeper. His wife went insane & his son was convicted of embezzlement.
House later became apartments, then restored in 2010.
Now a single-family home—currently listed for $6.95 million
Mansard Roof (slate) with dormers
Convex “hooded” tower roof
Double brackets and denticulated brackets
Pronounced Limestone Lintels
Eastlake Porches in Iron (Art Nouveau)
Photo 12 – Foyer
Photo 13 – Kitchen
Photo 14 – Dining
Photo 15 – Spiral Staircase
Photo 16 – Sitting Area
Photo 17 – Primary Bedroom
Photo 18 – Primary Bathroom
Photo 19 – Rooftop Terrace
Photo 20 – Custom Shower Area
Home of Edward Warnecke
1417 N. Hoyne
Style: Italianate
Circa: 1879
Features: detailed wood-columned side porch and rolling lawn—classic Victorian style.
Home later fell into deep disrepair.
English basement design kept the kitchen below to reduce heat and odor—think Bridgerton or Downton Abbey.
Stop 6 – 2131 W. Le Moyne – Sausage Factory Cottages
- Style: Italianate
- Circa: 1888
Two brothers built this cottage and the one next door.
Shared coach house between them was used for a sausage factory.
Current owners bought 2018 around 7 years ago—in disrepair.
Fully gutted and restored, including the coach house.
Dug a basement—original joists were sitting on dirt.
Worked with Landmark Chicago and National Landmark on restoration.
Took 3 years to complete.
Refinished original windows, doors, and trim (or matched it).
Installed geothermal heating in basemet
Photo 21 – Existing Condition When Purchased
Photo 22 – Existing Condition When Purchased
Photo 23 – The Dig
Photo 24 – The Dig
Photo 25 – Pouring The Concrete Basement
Photo 26 – Patched Staircase Reinstalled
Russian/Turkish Baths
Circa 1910
Lloyd & Klein
In the 1800s, regular bathing wasn’t common in Chicago.
By 1900, hygiene and health became linked—bathing grew popular.
Bathrooms and hot water were still rare in many homes.
Sewers and water lines reached this area starting in 1873.
Thousands lined up for free hot showers from the city.
Chicago opened the world’s first free public bathhouse in 1894.
Each person got free soap, a towel, and 20 minutes total.
Water ran full force for 7–8 minutes.
By 1919, 19 bathhouses existed in the city.
Prohibition cut revenue—eventually bathers had to pay 5 cents!
Photo 1 – Facade with Aquatic Motif in Terra Cotta
Photo 27 – Men’s Bathhouse Line
Photo 28 – Women’s Bathhouse Line
Photo 29 – Bathhouse on Cullerton in Pilsen
The Robey Hotel
- Name: North West Tower — Wicker Park’s first skyscraper
- Style: Art Deco, Flatiron shape
- Built: 1929
- Architects: Perkins, Claten & Hammond
Location Buzz
- 30,000 people + 20,000 vehicles passed by daily
Design & Structure
- 14 stories, Indiana limestone—tallest on the Northwest Side
- Grand entrances on North & Milwaukee
- Lobby with Grecian marble and Art Deco details
Target Tenants
- Built for doctors, dentists, and lawyers
Modern Features (for 1929)
- High-speed elevators with automatic leveling
- Enclosed fire stairs—no exterior fire escapes
- Sub-metered electricity at wholesale rates
- Oil-burning boilers for clean, quiet heat
Medical-Grade Utilities
- Suites had gas, air, water, and electricity
- Ready for surgery, dentistry, or lab work
- Each suite individually metered
Photo 30 – Chicago Tribune Cover 1929
Photo 31 – Rendering of original building
Fly Boy and Lil Mama
- Created by Brantley—”cartoons history forgot”
- Inspired by the Tuskegee Airmen (WWII Black pilots)
- Goggle-wearing characters reflect modern kids
- Honor the spirit of courage + breaking racial barriers
About Hebru Brantley
- Exhibited worldwide: Chicago to London to Hong Kong
- Shown at Art Basel, Scope NYC, Frieze London
- Featured in major media: Forbes, HypeBeast, Tribune, etc.
- Collectors: LeBron, Beyoncé, George Lucas, more
- Collabs: Nike, Adidas
Nevermore Park
- Opened in Pilsen (2019), 6,000 sq ft immersive world
- Featured Flyboy & Lil Mama, drew 23,000+ visitors
- Closed during pandemic
Now
- Based in L.A., building the Flyboy Universe
Photo 32 – N. Damen (just north of 6 corners intersection)
Photo 33 – Uptown (side of Uptown Broadway Building – Leland)
Photo 34 – Navy Pier
Photo 35 – Tuskegee Airmen
Photo 36 – Red Tail Fighter Airplanes
Photo 37 – Batboy “Flynamic Duo”
Photo 38 – Sparrow “Flynamic Duo”
I Am A Man Mural
Mural by Chicago native Darius Dennis
Honors a pivotal moment in Black history
Recreates a photo from MLK’s funeral
King gave his “I’ve Been to the Mountaintop” speech in Memphis
Assassinated the next day
“I Am A Man” became a lasting civil rights symbol
Photo 39 – Clifton Street Art Gallery in Uptown
Photo 40 – Clifton Street Art Gallery in Uptown (above Jeremy Novi’s “Koi” mural)
Flatliners Filming Location – David’s Apartment
Photo 41 – 1990 Flatliners Poster
Address: 1270 N. Wolcott Ave
Style: Second Empire, late 1800s
Next door: 1266 N. Wolcott – Italianate, late 1880s
Movie Details
Flatliners (1990) filmed here
Plot: Med students experiment with near-death experiences
Cast: Kevin Bacon (32), Kiefer Sutherland (23), Julia Roberts (22)
Tagline: Some Lines Shouldn’t Be Crossed
Photo 42 – 2017 Flatliners Poster
Remade in 2017 (Netflix), Kiefer returned at age 49!
Tagline: Cross the Line – Death Will Follow You Back
Also starred Elliot Page (he/him)
Photo 43 – Scene from the original movie
Social Media Creator Services
Professional Interior Design Services
Architectural Photography Prints
Route 66 Content Coming Soon
Walking Tours and Private Tours:
Art Deco / Oldtown / Wicker Park / Ravenswood Manor / Graceland Cemetery / Fine Arts Building
Second Fridays in the Fine Arts Building Open Studios from 5 pm – 9 pm
Doorways Of Chicago Coffee Table Book Launching in 2026 – Trope Publishing
I’m taking my tours abroad! My curated trip to Peru launches in 2026. Architecture, Ancestry & Ancient Doorways: Peru with Ronnie
Authors On Tap: Keir Graf & Ronnie Frey
Please join us for a very special Exile in Bookville and Fine Arts Building event! On Friday, June 13th at 7:00pm CT in Curtiss Hall (10th floor) of the Fine Arts Building, Exile MVP Keir Graff will discuss his new book, Chicago’s Fine Arts Building: Music, Magic, and Murder. Keir will be in conversation with Ronnie Frey!
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