His choice of song brought down the house at Park West in Lincoln Park.
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"Everybody was fantastic, so I knew that every person was going to figure out a way to make themselves stand out. And, that was the way that I knew to make myself stand out. And, I love opera. I appreciate classical music very much. I got some training in that," Jackson said.
The 45-year-old beat out more than 500 contestants vying for the top spot.
WATCH: Chicago Sings Karaoke competition winner joins ABC7 Chicago
Chicago Sings Karaoke competition winner joins ABC7 Chicago
And no, Mayor Lori Lightfoot was not a contestant. She and the city's Department of Cultural Affairs and Special Events kicked off the citywide competition last month, holding auditions at 18 venues across Chicago.
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Six performers made it to the finals, but after competing in two rounds, that six came down to only one.
Chicago announces 6 finalists in kaaoke competition
As the winner, Jackson walks away with $5,000. His advice to competitors next year is to just have fun.