6 Things You Never Knew About Oak Street & The Gold Coast

Chicago is a city rich in history, legend and stranger-than fiction-secrets.

From the chilling chapter told in the book Devil in the White City to tales of Al Capone’s secret underground exit at The Green Mill, it’s clear that this city has a fascinating past.

But what about our neck of the woods?  Do Oak Street and the Gold Coast neighborhood have any secrets you might not know?  Read on to find out…

1.  An Isolated History

These days, the Gold Coast couldn’t be more central or well-connected – its dream location is at the very heart of The Windy City.  But that wasn’t always the case.  Up until the early 20th century, it was a sort of isolated enclave that was home to some of the city’s richest residents.

When the Michigan Avenue Bridge (now known as the DuSable Bridge) was built in 1920, however, it connected this lovely lakefront area to the rest of the city, which resulted in massive new developments, like high-end shopping that the area is still known for today.

2.  The Astor Connection

This might surprise you, but the Gold Coast wasn’t always the Gold Coast.  In fact, it was once The Astor Street District.  And no, it wasn’t because the famous businessman John Jacob Astor resided here, but rather because his name conjured up the image that the area wanted to be associated with.

3.   The Playboy ConnectionGold Coast 2

The Playboy Mansion is now synonymous with Beverly Hills, but the original was here in the Gold Coast.  Hugh Heffner bought the place at 1340 N. State Parkway in 1959, and it served as the center of his infamous and luxurious lifestyle throughout the 60s and early 70s.  In 1974, Heffner donated the building to the Art Institute of Chicago for student dorms.  The building was bought and turned into 7 condos in 1993, one of which sold for nearly $3 million last year.


4.  Landmark Achievement

Much of the Gold Coast neighborhood is protected as a historical landmark as it was placed in the National Register of Historic Places in 1980.  This is due to the area’s many notable architectural landmarks and its significant role in Chicago history.

5.  The Palmer CastleGold Coast 3

Potter Palmer was arguably the founder of the Gold Coast neighborhood.  While the vast majority of his wealthy contemporaries, like Marshall Field for example, were building magnificent homes in the Prairie Avenue district (now the near south side), Mr. Palmer was snapping up swampy lakeshore property to the north.  Here, he built the Palmer House Hotel as a gift to his wife and the Potter Palmer Homestead, a Gothic-style urban castle that presided over 1350 N. Lakeshore Drive before it was demolished in 1950.

6.  The Crème de la Crème

Michigan Avenue as famous shopping district was born in the minds of city planners at the start of the 20th century.  They widened the street and began to build a commercial center inspired by Paris’s Champs-Élysées.  Progress went along swimmingly until the Great Depression brought it to a halt.  But 1947 saw a resurgence and a plan to make the avenue into “The Magnificent Mile.”

Over the years, the area established itself as a world-class commercial district.  And its development brought about the transition of Oak Street from elegant residential block to the upper echelon of Mag Mile shopping, where exclusive boutiques could find charming spaces that were a bit removed from the hustle and bustle of the avenue.

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