Chicago let slip a 2-0 lead which came courtesy of a Jalil Anibaba double, but finished the night off with a late winner.
Jalil Anibaba opened the scoring in the 11th minute with a glancing header from Pavel Pardo's cross. The rookie defender nodded home his second of the night 20 minutes later with a looping header to the far post from a Cory Gibbs ball in.
Emilio Renteria cut the lead to 2-1 in the 72nd. Eddie Gaven supplied the cross and Renteria put an athletic finish into the net, hitting a half-bicycle from a feet above the ground.
Eight minutes later Dilly Duka leveled the match. A terrible clearance fell kindly for Duka, who smashed home his shot with some vengeance.
Chicago would have the last laugh, however, with Diego Chaves scoring the winner just moments later. Dominic Oduro broke in on goal. His poked shot fell right into the path of Chaves, who tapped it home for a 3-2 lead that Chicago would keep for the final eight minutes of the match.
Emmanuel Ekpo was ejected in the final moments of the match.