A term originating in the Chicago metropolitan area describing a particular style of semen facial
where the man lovingly and perfectly bisects his partner's face with his ejaculate as to avoid said partner's eyes. A Chicago Ending typically describes the man's intent rather than deed, as it is difficult to execute a perfect Chicago Ending in practice.
OMG, Andy took me out to dinner in Chicago last night, and later gave the me the best Chicago Ending
. It was so sweet and fitting.