We recently traveled to Ireland from the USA, with my MIL flying from Indianapolis to O'Hare connecting with us (hubby & me) from Milwaukee. I bought two travel insurance policies through InsureMyTrip.com primarily to cover us in the event of medical emergency/evacution. Fortunately both came with very basic trip delay coverage which paid on additional expenses we incurred, both going to and returning from Dublin.
My MIL missed her connection due to mechanical issues in Indy, so she was delayed to Dublin by one day. She incurred hotel & meal expense, plus the added expense of gas + tolls for the additional trip from County Wexford back to the Dublin Airport. The policy we had for her, paid in full.
On the return home, hubby and I were delayed significantly out of O'Hare due to weather (the airport in Chicago had been closed for about an hour, causing some cancellations as well). Anyway, we incurred added expenses for a meal at the airport, plus having to have someone drive down to Chicago (from Milwaukee - roughly 100 miles each way) to pick us up. Our policy also paid in full.
The policies cost $64 (MIL) and $78 (us) and paid out $217 and $82 respectively.
The claims process was easy and the service provided by the two insurance companies (Global Alert and TruTravel), flawless. I would recommend InsureMyTrip.com for anyone looking to purchase travel insurance.
The biggest challenge will be understanding what risk you are looking to insure against and buying only what you need. "Full coverage" policies would have been over $150-$200 each but we didn't need to protect against much of what a full service policy covers.
Lastly, if you are buying for medical coverage and/or evacuation be sure you read and understand the preexisting conditions clause(s). Often you can get them waived if you purchase your insurance plan within a few days (or weeks) of making your first deposit or payment towards your trip.
I hope this info helps others as they plan upcoming trips. In this day and age of flight delays and cancellations, I cannot imagine taking an expensive trip without having the protection provided by travel insurance.