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Summer Jobs That Shaped Chicagoans

Chicago areaWednesday, July 15, 2026

Growing up in Chicago, summer jobs were a rite of passage. For many, these gigs were more than just a way to earn some extra cash - they were a chance to learn new skills, meet new people, and create lifelong memories. Take Tom Judge, for instance, who worked as a guide-lecturer at the Museum of Science and Industry when he was 17. He still remembers the U-505 tour and the trophy room speech that started it all.

Others had jobs that required a bit more elbow grease. James Beasley spent his summer of '92 painting billboard posts along I-65 from Gary to Lafayette. It wasn't an easy task, but it got him outdoors and enjoying the scenery. Then there was Jordan Mainzer, who worked as gate staff at Ravinia and learned two valuable lessons: how to deal with boredom and how to handle entitled people.

Some summer jobs were a bit more unusual. Laurie ShoulterKarall spent two summers detasseling corn in fields just west of Naperville. Walking the rows and manually pulling out tassels from female plants was hot, sweaty work, but it gave her a deep respect for farmers and farm workers. Danni Coutee worked at a fruit stand in River West, while David Kraft spent his summer of '68 working at a hot dog stand at the Chess Pavilion at Oak Street Beach.

For some, summer jobs were a chance to make some serious cash. Marty Regan worked at the Taste of Chicago in 1982 and made $800 over three days selling snacks and drinks to festival-goers. His friend Joey was right there with him, raking in the same amount. And then there was Angela Cantu, who worked as an usherette at the circus in Marriott's Great America back in the mid-1970s.

Not all summer jobs were glamorous, though. Bob Steinmetz spent three summers loading clothes and chemical cleaners in the back of a dry cleaner, earning just 90 cents an hour. But despite the hard work and low pay, these jobs taught valuable lessons that stuck with these Chicagoans for years to come.

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