Cargo, Chicago???

Yes, Planemasters is in Dupage. You wouldn't likely be based there. Their cargo side is UPS. They're a good company; you may even say "reputable." PM me if you have questions. Back to my cave.
 
I would second planemasters but you would end up in Kansas the fed ex feeder is in Milwaukee they are CSA Air good company however unless your 50 or over your the underdog but still not impossible. I think both company's are overstaffed and not hiring let me know if you need more first hand info.
Nick
 
There is also the shorts operator in mke or freight runners (not the best company it will get you by in a pinch) I think the shorts are air cargo carriers
 
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