Answer
Chicago was not on Wiley Hardeman Post's flight plan during his historic solo flight around the world in the Winnie Mae. Post took off from New York on July 15, 1933, and made stops in Harbor Grace, Newfoundland; Berlin, Germany; Moscow, Soviet Union; Fairbanks, Alaska; and Edmonton, Alberta, before returning to New York on July 22, 1933, setting a new world record for the fastest circumnavigation of the globe.