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Yes. As long as you paid some portion of the trip on the Chase card. There are good walkthroughs on what docs to keep/steps to take. You’ll front any expenses and they’ll reimburse you. And if you’re already in the airport, ask for a “military excuse” to document the delay. US carriers will know what that means.
I'm in Pakistan right now as well. Fly into Islamabad and drive to Lahore. Ask airline to change arrival.
If it’s on the same ticket, and sometimes same alliance, the first carrier is responsible for getting you to your final destination even if you’re changing carriers. Even if that’s not the case, the second carrier may move you to a different flight without charge if you explain the situation. Can’t help with the insurance question though!