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Looks like a permit was issued on July 19, 1905 for the theater building. A building permit was issued for the current garage building on this spot on April 17, 1926.
Originally to be called “Old Robey Rink”, it opened as Sittners Banner Theatre (see 1910 entrance photo) and the following from the Wicker Park Eagle, Feb 10, 1910:
Old Robey Rink, 1611-15 N. Robey St. is the new theatre which will open its doors to the public. Entirely renovated for $10,000, will contain a large stage with steel curtain and balcony with a seating capacity of about 800. F. C. Smalley, of the Smalley Manufacturing Company 1835 W. Lake St., who has the lease for the theatre, says “nothing but high class numbers will be staged.” Wm. J. Van Keuren with offices at 78 La Salle St. is the architect.
An 1888 Chicago Tribune article on Milwaukee Avenue mentions a “Star” Theater; I’m wondering if it was originally a smaller theater and was torn down and rebuilt at the same address in 1907.
From the article (Aug 4, 1888):
“The Odd-Fellows, Masons, and other secret societies are well represented along Milwaukee avenue. Aurora Turnhalie is one of the institutions of the city. Milwaukee avenue has a theatre, the Star, two miles from the centre of the city. Milwaukee avenue is to have a club-house, too, unless a movement set on foot by such men as John Buehler, Fire Secretary Petrie, George Rahifs, C.H. Plautz, and W.F. Weimers results in failure, and they know no such word.”