Booking the insurance in the first place was easy. I was hoping the claim would be similar.
Allianz sent me a separate email a few minutes after I received my Amtrak ticket. It had a link to my full policy and other details, which I admittedly did not read until I needed them.
In the meantime, I started reading Allianz's policy that I admittedly had not read when purchasing. For a "travel delay" my policy said I was entitled up to a daily limit of $150.
To Amtrak's credit, the rebooking line when we finally arrived in Chicago was long, but moved quickly. As I waited, a representative went down the line with new tickets, and hotel and food vouchers for everyone who had missed their connections. I waited maybe 15 minutes in total.
Another important note: Amtrak did offer hotel vouchers for those of us who needed to wait overnight. I had rescheduled meetings for early the next day as a result of the delayed train, and didn't feel like schlepping to The Loop during rush hour from Midway Airport. It also proved a worthwhile moment to put travel insurance to the test.
Sitting in Union Station — while contemplating the plight of this beautiful depot of yesteryear compared to its companion in New York — I found a hotel that fit in Allianz's limit for "travel interruption" accommodations and booked a room.
The only downside to the plan, of course, was having to front the money and not knowing if the travel insurance would actually work.
A day later, and a few dollars shorter, I headed west on the same train as originally planned (and even lucked out with a room). But back in New York four days later, it was time to file a claim.
Filing the claim was easy, all I needed was my email address or policy number, and the date I departed for my trip. The form was simple and quick, all I had to do was upload my hotel receipt. It didn't even ask for proof of my delay.
Six days after my claim was submitted, a check showed up in my mailbox.
Not only was it sooner than I expected, but easier too! I had worried that I would need some way to prove my train was delayed significantly enough to require a hotel stay, but that was not the case.
All things considered, the travel insurance was easily worth $17