MLS: Toronto FC 1 Chicago 2
This loss by Toronto FC means they miss the playoffs for a sixth straight campaign and also extended their winless streak to eight regular-season matches.
On the flipside, Chicago's victory pushes them up to second place in the Eastern Conference.
Uruguayan midfielder Alvaro Fernandez (12 minutes) and veteran Chris Rolfe (42) scored for Chicago (14-8-5).
In between, Toronto missed three gilt-edge chances as midfielder Andrew Wideman as well as Amarikwa and forward Eric Hassli all failed from close range to put the ball behind Chicago goalkeeper Sean Johnson.
The 14,623 fans at BMO Field finally had something to cheer about when French striker Hassli replied for Toronto in the 79th minute.
The Reds have now given up 50 goals this season and the struggling club is 5-73-21 all-time when conceding the first goal.
Not helping the home side's cause was the fact they were missing several regulars because of injury and those on international duty.
In their places were players with fewer than 10 games to their name, including defender Darren O'Dea, midfielder Aaron Maund and forward Quincey Amarikwa.
They will be back on the pitch on Saturday afternoon when they host the East's second-worst team the Philadelphia Union.