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The Zanzibar Motel on 81st and Stony Island comes with cheap whores stocked in the minibar.
If you are looking for softer sheets and more expensive whores I would recommend The W on Adams. The problem with most hotels in Chicago is that they haven't been revamped for this decade so you are sleeping on 1990's mattresses even in the top line hotels. With both the W's you don't have this problem.
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I've trusted my sites to them for over a decade...
Webair, bitches.
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