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Craig Wenokur has worked as the Vice President and Managing Director of Operations at Wendella Sightseeing Co. Inc. since 1987. Prior to that, they were a Radio DJ at WGEZ-AM Radio from 1981 to 1982.

Craig Wenokur attended Beloit College from 1979 to 1983, where they pursued a Bachelor's Degree in History. Craig then went on to enroll at Columbia College Chicago from 1988 to 1991, where they obtained another Bachelor's Degree, this time in Television Production.