Here is an update.
Booked a trip to Istanbul, Flights with CSP, Hotel with Hilton Reserve.
Since my hotel was not booked using CSP, I thought I would make a claim with citi for the hotel portion. After sending a large amount of documents, I was told my claim is not qualified because a "hotel stay is not a trip". Looks like it is my mistake so I'll swallow the loss of a few hundred dollars.
claim was denied by citi's outsourced agency: AMPIDS Property Casualty Insurance Company
Benefits Assistance Center
c/o Program Administrator at Sedgwick Claims Management Services, Inc.
PO Box 89405
Cleveland, OH 44101-6405
So beware, if you had a road trip planned, and you don't have common carrier travel as part of the "trip", it is not a trip. Your non refundable hotel reservations are not covered. In that case I would recommend that you book a refundable air ticket to make this a "trip". That is what I should have done if I had known how they would interpret.
Anyway, the better solution would be to always book with CSP or other card. This is what their benefit guide considers a trip
Covered Trip means any pre-paid tour, trip or vacation when some
portion of the cost for such travel arrangements less any redeemable
frequent flyer miles, points, coupons or certificates, or other types of
redeemable Rewards has been charged to your Account:
The CSP insurance company called Crawford & Company was relatively easy to work with and honored our claim for the flight. We had a combo of paid and award ticket. They covered both of those flights. I'm extremely pleased with the way they handled the situation.
I have an electronic copy of the chase benefit guide for CSP and fairmont, citi's benefit guide for hilton reserve and executive club card as well. PM if you want that.