Rush Street is the gay main artery of the near North Side. The well-lit mile of fun and frolic has every type of music for dancing and listening. The bands and singers provide thrilling entertainment from twilight to down.
Now:
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Doesn't even look the same. I did find some history and an even more interesting story you can read at the awesome
Chicago Crime Scenes Project:
In its 1950s heyday, Rush Street was packed with upscale nightclubs, cafes, and dance halls that kept the near North side swinging. Besides the Cloister, the Bambu, the Tradewinds, Mr. Kelly's, and The Happy Medium were some of the most popular clubs, and in just about any given week, one could hear performers there who today would be considered legendary, if they weren't already then.
Over time, however, the neighborhood began a slow decline. In 1960, the owner of the Cloister Inn faced a lien on his establishment due to unpaid taxes, and he sold to a new group, which renamed the basement club "The Celebrity Lounge." Great musical acts, including trombonist Si Zentner and the King Fleming Trio continued to play the Maryland throughout the early 1960s.
By the late 1960s, however, the North Rush Street area had taken on a distinctive seediness, and the small size of the Maryland's rooms, in comparison with those of more luxurious modern hotels, made it an especially unwelcome host for business and entertainment travelers. In time, most of the rooms became occupied by long-term tenants, who paid around $175 per month. The Celebrity Lounge closed and a dirty go-go club, the Rush Over, re-opened in that space, while an oyster bar, Alfie's, inhabited the first floor restaurant space. Alfie's eventually converted to a disco in 1974, offering "Plastic hanging plants, leatherette swivel chairs, some plaid upholstery....pulsating strobe lights and a mirrored ball," in the words of the Tribune's unimpressed reviewer.
Like the old Cloister Inn, The Tradewinds and Mr. Kelly's also closed, and seedier establishments such as an adult movie house and The Candy Store -- the latter of which was a strip club and thinly-disguised brothel -- took over all along Rush during the 1970s.
By 1980, the decline of the Rush Street district was complete; it had become something of a skid row on the Northside, and the Maryland was falling apart, literally. Of the 300 rooms, only 50 were occupied in July, when the hotel was sold to a group of far-sighted investors, who renovated the buildilng, combining rooms to create 87 plush condos, and adding the distinctive bay windows visible on the bulding today. They moved the entrance around the corner to Delaware Street; the previous main entrance was on the Rush Street side, near where the entrance to the high-end fashion shop Intermix is now.
Their investment turned out well, though it took a few years. Today, the adult theaters and SRO hotels are gone from the area, replaced by couture stores like Ikram and expensive boutique hotels like the soon-to-open Elysian. There are few signs of the swinging days of the Cloister Inn and Celebrity Lounge here today. The upscale clubs two blocks north, centered around Rush and Bellevue Place (recently, though universally, known as the "Viagra Triangle" for the prevalence of graying divorced men throwing cash at bleached blondes), offer only a faint echo of those that once brought some of the greatest musicians in history to Chicago. The seediness of the 1970s and 1980s-era Rush Street can be experienced to some degree at the top end of Rush, at Division St., where streetwalkers and drug-pushers mix with boozy carousers every weekend.
The basement of 40 E. Delaware Place, where jazz once blasted from the stage at the Cloister Inn, now holds bicycle storage for the residents of the upscale condos.
