I have not been at ORD UA Terminal for a long time. But I recall that the duty free shop there is small and I don't think I see any Apple products. I would buy it at the store downtown even though with sales tax.
I know at SFO International Terminal there are vending machines selling Apple products.
Prices of electronics (and not only) in the U.S. are generally (i.e. with a few exceptions) so cheap compared to other countries, that when you buy downtown you're essentially buying 'duty free'. If you want to avoid paying the state tax as well, I believe you should buy mail order and ship to the state you'll be visiting (though I understand this may not be so easy if you're visiting for a few days and staying in a hotel). But I've done it, so it is possible.
The duty free stores at ORD are very small and definitely don't sell them. I don't recall seeing the vending machines selling them as has been mentioned (and I've also seen) at other domestic US airports, but that doesn't mean they aren't there.
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