Is there "trip insurance" for this?
 

I was reading an article this morning about getting air deals by combining segments where there are deals available with other separate flights. For example, instead of flying SFO-IST-SFO, fly SFO-IAD-SFO, and separately ticket IAD-IST-IAD, because Turkish Airlines has a deal going on between Dulles and Istanbul that would save us close to $1000. Of course, that means there's a risk of missing the IAD-IST flight or the IAD-SFO flight if the other flight is delayed or cancelled. So, I was wondering if there's trip insurance available that would cover this possibility (basically, pay to get you where you were going if you miss the second flight because the first flight is delayed or cancelled).

R u going to Turkey? On my very long list of places to go.
To your question, I tried to find insurance like you describe a couple years ago and was unsuccessful. Be interested to hear if someone knows of any trip insurance like that available.

I don't think there is because you are intentionally adding a big risk to your travel arrangements.

There might be some policy out there that would cover you - check www.insuremytrip.com - but note not every type of insurance is sold in every US state. But I wouldn't be surprised if it isn't more expensive than the savings you'll make using this method.

Try doing a multi-city booking using Expedia or some such and see how the bottom line compares with the two separate itineraries.

Thanks all. We haven't found any insurance (yet) and won't take the risk of two separate itineraries without insurance, so it looks like we'll just have to bite the bulletin and get the best multi-city itinerary we can for the best price (hopefully with an available upgrade, or ability to buy a biz-class segment for miles).

What about going to DC one day early and staying at a hotel near the airport which should be economical? This way there is little chance of missing the flight save for natural causes like superstorm Sandy. Speaking of which we missed our flight back to Chicago form Madrid as the connection in Newark was cancelled. UA wanted to send us back 6 days later which was impossible for us so we were forced to buy our own tickets to return. However this was fully refunded by my insurance plan which we purchased thru insure trip.com. We chose American Express as the plan provider BTW.

I suppose that "we" are 2 people, so $500 each?

What dates? I'm surprised that the difference would be that great.

Looks like IAD-IST is a late night flight, after 11PM. SFO-IAD is pretty well served. United can get you to IAD at 2PM with several backup options if that 6AM was actually cancelled. A redeye the night before gets you to IAD early morning, again with those backups.

Arrival time of IST-IAD is 17:45 on the date I checked so the backup options if that is late would be more limited, but still as late as 10PM.