Duty-free idea in US...would this legaly work???

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Going overseas and leaving from ORD...and...parking my car at one of the airport lots: So, my idea is to go through security (obviously I'll have my boarding pass) and then go to a duty-free store, buy as much stuff as I can, and then leave the terminal and go back to the parking lot and put the stuff into my car, and return to the terminal. Reason for: I travel light, and I don't wan't to haul the stuff for 2 weeks while I'm overseas bcause I'm not checking any baggage, just carry-on and personal bag. Any problems with this idea? Thanks in advance!

We don't buy duty-free anywhere but I've noticed that duty-free items purchased in US airports are delivered to the purchaser as they enter the plane for the international flight.

Two or three rambling thoughts here ----- most airports (don't know about O'Hare) deliver
your duty free purchases at the jetway when you're boarding the aircraft .... secondly, I don't find
that duty free is all that good a deal .... in the olden days there was a substantial savings, but
I don't think those savings exist except at some obscure airports. And, I lost my train of thought as
to the third comment >:) Let us know how your plan works out.

Just remembered the third point .... when you go through security, TSA checks passport/boarding pass,
marks on the boarding pass and, most likely records that you've been checked through .... so now,
when you come back through, that's going to be, for sure, a red flag.

It's been a while so I'm not sure about this--but my recollection is that duty-free purchases, at least alcohol, are delivered to the passenger at the end of the flight. (I think they don't want passengers to have access to their own booze during the flight.) Like Geoff, I believe duty-free savings aren't all that great anymore. Discount stores often offer better deals.