Greeted by a red glowing and glittering arrow overhead, one immediately knows that they’ve reached the heart of Boystown, Chicago’s closest thing to a red light district, as they approach Cocktail. Sometimes welcomed by a drag hostess (often Chicago Cher or Miss Floozie), patrons enter a sort of progressive house pub where go-go boys frequently ascend the bar room floor, usually on Tuesday and Thursday nights.

Exposed brick offers a contrast to the large wooden bar that centers the space while velvet curtains frame the storefront windows. Perched on the corner of the neighborhood's most traversed intersection, the window space often fills up with people watchers, sometimes gawkers.

Popular with an out-of-college to middle-aged crowd, the patrons are mostly gay men, a few straight friends mixed in. With more of a progressive pub feel than mega nightclub, the management boasts live DJ’s five nights a week. Most popular nights are the go-go boy Tuesdays and Thursdays with an extension of the box dancers to some weekend nights.