3905 S Cottage Grove Ave.
The Macomba Lounge was an after-hours owned by Leonard Chess, who would later found Chess Records. Chess had invested the money made from the two liquor stores he owned into refurbishing an old eatery for the venue. His brother Phil held its liquor license and eventually took it over when Leonard began running the Chess label full time. The Macomba was initially patronized by prostitutes and drug dealers, but quickly developed a reputation among musicians as being a spot to hear jazz and jump blues. It was destroyed in a fire in October of 1950.