I've used the Chase travel insurance at least twice during mechanical cancellations. I can't remember what the terms say, but it was relatively painless - as far as filing an insurance claim goes. I honestly didn't check to see if UA was going to give me anything. I just walked to the hotel of my choice, bought some pajamas, contact lens solution and a tooth brush and went to sleep. The carrier, who of course isn't Chase, was fine. It's not like they don't do this stuff day-in-day-out. The portal was relatively easy, and UA issued a delay letter in about 2 weeks. I got the maximum amount they'd pay for the hotel, and paid the difference out of pocket. Much easier than waiting in line for a voucher, then getting in line for the shuttle to HoJos. That said, my last mechanical misconnect, I took the UA hotel voucher, at DIA, and it was fine as well.