Construction at Leland and Broadway, 1920s

Construction on Leland looking toward Broadway; you can see the rooftop marquee of the Uptown Hotel. The Uptown Hotel, aka the Plymouth, was torn down as part of the redevelopment of the Goldblatt's-to-Borders project. To view a bit of the terracotta that once graced it, you can peek into the lobby of the current condo building on the site.

Leland at Broadway

I'm not sure of the exact date of this photo, but it appears to be 1920s. You can see the very top of the Uptown Hotel's marquee at the top. This is looking toward the stretch of Broadway between the Wilson El stop and Lawrence, where the tracks go across the road.

Kenmore South from Leland a Hundred Years Ago

An idyllic stretch of Kenmore a hundred years ago, before most of the big entertainment venues, including the Uptown Theatre, were built.

Our Lady of Lourdes Parish School

A 1911 view of the intersection of Leland and Ashland with Our Lady of Lourdes Parish School.

Sheridan South from Leland, Uptown Chicago

While I love the great entertainment history of the neighborhood photos like this make me a bit wistful. I wonder what these families thought as "progress" creeped into Uptown, along with the apartment hotels, clubs, restaurants, dance clubs, and theatres.

Sheridan South from Leland

Another 100-year-old-view of Sheridan Road, looking south from Leland. This stretch has changed a lot over the last century, with homes coming and going, businesses coming and going... There are a few pockets of Uptown that still look like this, but not many. If you ever feel like taking a stroll through the past, take a walk down Castlewood to see samples of some of these vintage homes.

Leland from Beacon, Uptown Chicago

How wonderfully overgrown with trees and shrubs, you just know this street was blissfully cool on a summer's day.

Leland from Magnolia

Isn't the old saying "you can't see the buildings for the trees" or something like that. Here is a 1911 view of Leland Avenue looking from Magnolia.

Kenmore and Leland, 1980s

pre-condo, a photo by Jonie Snake on Flickr.

Used with permission of flickr's "Share on Blogger" feature. Check out Jonie Snake's photo stream for more excellent photos of Uptown in the eighties.

Today:


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Lewis A. Weiss Hospital Groundbreaking, Uptown Chicago, 1952

Relatives and friends of the late Louis A. Weiss, businessman and philanthropist for whom the hospital is named, participated in the ground-breaking ceremony for the new $2,500,000 memorial hospital on Marine Drive between Leland and Eastwood. Left to right are James R. Gersonde, former director of the Chicago hospital; Dr. Siegfried Strauss, president of the board of directors of the new hospital; Dr. John J. Sheinin, president of the Chicago Medical School; Dr. and Mrs. Jerome H. Hirschmann, son-in law and daughter of Lewis A. Weiss, and their son, Ricky Hirschmann, 4.

Image currently available on eBay. Item number: 270787829984

Leland and Kenmore, 1914

A rare view of the intersection, currently on eBay

Here's how it looks today:


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Clark and Leland, Chicago, 1955

This one is a little further out than we usually find for images of Leland. It is currently for sale on eBay

Sheridan and Leland, Uptown Chicago, 1936

This series includes one of my favorite terra cotta buildings in Uptown, with the large faces at the top.

Looking back on the dozen or so posts from this evening, all I can wonder is "what happened, Uptown?" So many more fabulous buildings were lost than I ever imagined. Such vibrant, clean streets and lots of retail opportunities. I can see why it was the place to be back in the day.

Matchbook from the Leland Hotel, Leland and Racine, Uptown Chicago

A downtown hotel in the art of Uptown!

To see historic images of the Leland Hotel that we posted back in 2007, go to: Leland Hotel

1254 Leland, Uptown Chicago -- Home of the Touhy Gang

Roger Touhy (1898-December 16, 1959) was an Irish-American mob boss and prohibition-era bootlegger from Chicago, Illinois. He is best remembered for having being framed for the 1933 faked kidnapping of gangster John "Jake the Barber" Factor, a brother of cosmetics manufacturer Max Factor, Sr. Despite numerous appeals and at least one court ruling freeing him, Touhy spent the next 26 years locked in a prison cell. Touhy was not released until November 1959. He was murdered by the Chicago Outfit less than one month later (more at Wikipedia.)

On October 9, 1942, Touhy and six other men escaped from Stateville prison. Touhy and the others were eventually discovered living in a Chicago boarding house. Touhy and three others surrendered peacefully. The remaining escapees tried to fight their way out and were killed. Touhy re-entered Stateville on December 31, 1942, and was sentenced to an additional 199 years in prison for the escape. 

The above photo, available for purchase at time of writing here, is of 1254 Leland, where the Touhy Gang lived. In 1944, 20th Century Fox released a semi-biographical and highly fictionalized film based on Touhy's life, called Roger Touhy, Gangster.

To learn more about Touhy, read The Stolen Years.





and


When Capone's Mob Murdered Roger Touhy: The Strange Case of "Jake the Barber" and the Kidnapping That Never Happened 

Sally's 4650 Sheridan, Uptown,

 

A matchbook from Sally's, a 24-hour diner once located on Sheridan, between Wilson and Leland. 

A description of Sally's from a 1930s dining guide can be seen here: Uptown Restaurant Reviews.

Leland and Magnolia, Uptown Chicago, 1910

Looking east on Leland from Magnolia, 1910 (above) and on Google Street Views (below).


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Sheridan and Leland, Uptown, Chicago

Sheridan Road at Leland, you can see the church on Wilson in the far distance. Image courtesy Ben B.

Leland from Clarendon, Uptown Chicago

How's this for a big ol' shocker. Here's Leland Avenue looking west from Clarendon. Yup. that's right. Leland. The roads haven't even been paved yet.

Here's what it looks like today. A great big bunch of empty. And according to Uptown Update, it looks like it will be staying that way for a while.

Top image courtesy John Chuckman. Bottom image courtesy Google Maps.

Uptown (Plymouth) Uptown Hotel, Broadway at Leland, Built in 1912

Uptown Hotel
Fireproof
4700 Broadway at Leland
Chicago Illinois
The Uptown Hotel's Location is Perfect Winter or Summer
Theatres, Beaches, Shops, Chicago's Best Transportation
Elevated Express, Street Cars, and Buses at Door. Metropolitan Bus Station in Hotel.
Weekly Rates $7.00 to $12.00
Courteous Service. 150 Large Rooms. Telphone LONgbeach 6400

The Plymouth Hotel, built in 1912, was one of the oldest buildings in Uptown when it was torn down in 2003 as part of a development project. Preservation groups tried to get the developer to incorporate the building into its plan, as it was structurally sound and, according to Landmarks Illinios, capable of being adaptively reused. Unfortunately the developer felt otherwise.

The Plymouth was designed by George Kingsley, best known for his Reebie Warehouse on North Clark. It was the favorite hotel of Essanay's silent film stars. In the lobby of the condo portion, visible from the western side on Racine, is a rather large fragment of the original terra cotta ornamentation. For photos of the Plymouth and its destruction, go to Landmarks Illinois.