I asked a travel insurance related question about a week ago (I didn't receive any helpful answers), and there isn't much I found that would answer your particular situation. However, I did find this on another FT thread link about how CSP will cover travel delays.

Since you're concerned about a travel delay due to flights that you paid for with the Arrival card, you'd have to do some searching on the travel benefits of that card. I'm guessing that if you had switched the way you paid (hotel with Arrival, flights with CSP) then you would be covered for the prepaid hotel, but not sure about that. I think I've seen trip cancellation (not delay) covered by Arrival in their fine print. Might require a phone call to Chase to find out. Would be great for you to come back and post if you find out the answer.