Which brings up the fact that the trip delay coverage is very small, only up to $500. While that would certainly cover a night's hotel room in most situation, it could be a problem if you have a complex itinerary with prepaid flights every 2-3 days going to different cities, and prepaid hotel rooms, as I have done in the past.

For me, those itineraries have been either impossible to put on a single airline ticket (some airlines just won't mix), or the cost jumped by $5k - 10k (over total of <$1k to 2$k separate for coach).

If the first flight is delayed by more than 24 hours, it could cause the entire trip to be jeopardized, and it looks like in this case, Chase will only pay $500 max for trip delay, and prepaid expenses are excluded. Choices might be to stay at one destination for 24 hours less than planned, but IMO this isn't really adequate.

I have never been in such a situation in the past, but I have had medical cancellation where I couldn't leave on day 1 with this type of complex itinerary. Allianz did me right after I faxed about 35 pages of documentation for all the nonrefundable hotel rooms and tickets, including docs that these didn't get any refund. I have not had to deal with Chase trip cancellation coverage yet, fortunately, though I am relying on it primarily right now and am longer buying separate travel insurance policies. Now seems like a good time to compare the trip delay coverage between those policies and Chase, though.