448 W. Surf (above), and 2800 N. Pine Grove (below) were among the homes occupied at various times by the founder and leader of the North Side Mob, ex-singing waiter and floral artist, Dion O'Banion, in the early 1920s. 2800 N. Pine Grove stands opposite the Commonwealth Hotel, where, a few years later, entertainer Joe Lewis was brutally attacked after he switched venues from a Capone-controlled bar to a North Side Mob saloon.
Apparently Charlie Chaplin lived in the penthouse of 2800 N. Pine Grove, aka Brewster Apartments. I also have a note that it was featured in the movies Running Scared, She's Having a Baby, Child's Play, Hoodlum.
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