What to do when no search engine can find a connection that clearly exists

I’ve done the ‘international connection through JFK that I couldn’t book online’. I managed to get the flights booked over the phone, and the agent said that he was surprised that it couldn’t be done either.

(I was specifically going through JFK to meet a friend and then fly the rest of the way)

I was lucky that I had two hours for my connection, as the problem was that they were going through two different terminals, and they didn’t have a shuttle between them. Luckily, it wasn’t that far of a walk, I didn’t have a checked bag to worry about, and I managed to get through security in a reasonable amount of time. (and that the person behind me told me that I dropped my passport out of my shirt pocket when security insisted that I remove the shirt)

So, if you ever decide to force the booking through, be aware that you might have to collect your checked bag and then re-check it, be re-scanned through security, and possibly need a taxi or similar to get from one gate to the other … and you have no guarantee if you miss the connection because the first leg came in too late to be able to check your bag and such.

Most air travel websites do not look for a “connection” in the same way than mapping apps look for an itinerary on the road or train search engines look for train connections. They look for a connection that can be priced and booked (either directly or through a third party or travel agent). This adds a lot of complexity and many non-trivial constraints that are not always easy to understand for outsiders like you and me.

If for some technical or business reason a particular combination cannot be booked (no cooperation or “interlining agreement” between different airlines, one flight is fully booked, incompatible fares, connection under the minimum transfer time, etc.) there is no connection as far as those search engines are concerned, even if there are planes leaving and arriving from the relevant airports.

One exception I am aware of is rome2rio. It can show connections between different transportation modes and find tickets that cannot be booked together from one provider. Sure enough, it does find many Icelandair-domestic US flight combinations for your route. But you would need to buy tickets for each leg of the journey separately, which can have many unpleasant consequences (see other questions on this site for more on this).

I don’t know what the problem is in this particular case (Icelandair does have partnerships with United or Air Canada…) but since your question suggests those connections disappeared from most search engines at the same time and Rome2Rio can still find them, it’s likely to be related to changes in commercial agreements between Icelandair and other airlines.

But even for “regular” connections, the complexity is such that no website can exhaustively search all combinations and it’s often possible to find some connection that does not show up in a given website’s results.

The basic problem here is threefold:

1. you’re traveling at a very busy time of year (between Christmas and New Year),
2. you’re asking for a one-way flight (almost always proportionally much more expensive than a return), and the kicker,
3. you’re asking for a guaranteed connection, which is all flight search engines will ever return you; otherwise they can’t sell you the ticket!

That is, if you fly one of those $3000+ fares via Heathrow, it’s a single ticket and all airlines involved guarantee the connection: if one of their flights is late or cancelled, you’ll be put on the next plane for free. Since you’re unable to find any guaranteed connections on Icelandair from the US, I’d wager a guess that they don’t have any interlining agreements with any American airlines for flights from the US. (Which isn’t particularly surprising: Icelandair is a semi-LCC not affiliated with any alliance, plus a major competitor with US airlines on the lucrative trans-Atlantic sector.)

If you buy separate flights, it’ll be cheaper, but if you have any problems with your flights, you’re on your own. Personally, I’d still go for this option: the price difference is vast and you’ve got 7.5 hours in IAD, which is a pretty healthy buffer, plus your LIT-IAD connection is guaranteed so you’re quite likely to get there in time even if there’s a bit of trouble. But you’re still screwed if there’s a major blizzard or something, so YMMV.