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The question I still have is would a Chicago resident (where handguns are illegal) face arrest on a weapons charge trying to fly out of O'Hare. The problem being that it is illegal for a resident of Chicago to possess a handgun.
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I'm guessing here, but I'd say that the federal law which allows transport would not protect you in this case.
The law requires that the handgun is legal in BOTH the place of origin and the final destination. If the gun is illegal in Chicago, and you're from Chicago, then the gun is illegal.