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No doubts about asking for comp.
Big question is though - why did you check bags?!
I would have checked it separately. Never trust airlines with bags
yes you can and they will reimburse within reason. go to nordy rack and get some stuff, keep it under $300 and you should be fine.
on for having to go buy an outfit tomorrow morning? There are no United flights to my location that get in before 2pm so I can’t wait for my bag at the hotel.
I have Silver status but that’s it
Rule of thumb (for next time): if you’re checking in a bag, carry 1-2 days with in your hand luggage. Always.
Check you credit card coverage as well. I'd you're using any major credit card, there is a high chance you have this coverage already and can be reimbursed.
Sometimes by both the airline and the card.... Moral gray area?
Yes. Also check credit card benefits. You may be able to double dip.