My wife and I are planning a trip as a "babymoon," and are hoping to fly using award flights as we have more than enough miles - but as my wife is pregnant I am nervous that something might happen and we may need to cancel the flight. As a result, I'm thinking that travel insurance is a good idea. This is generally the advice that I have gotten from everyone - whenever traveling with someone pregnant, get the travel insurance when it's offered. However, if I am booking flights as awards, is the travel insurance still worth it? If I need to cancel a flight which was an award, but it has insurance, will I get the miles back in the same way that I would get the money back from a revenue ticket?
It depends on your airline's rules for redepositing miles if you cancel the trip... check this before booking.
In the most common case airlines charge a fee to cancel the trip and redeposit the miles, and insurance often covers this fee.
If you are a frequent traveller with elite status the airline may have a policy of waiving the redeposit fee.
A good source for more information is here