Open-jaw vs two one way flights

We'll book two one-way flights if they're a better fit for the comfort and convenience involved, and of course as long as they're not outrageously more expensive than an open jaw. Comparison shopping can resolve pretty quickly whether there's a significant cost difference involved. We've seen it both ways, ie no significant difference versus very expensive indeed.
Price is no longer our primary filter - we're willing to pay a little extra to make it easy on ourselves, whether it's with regard to routing, timing, or class of seating.

Two one way flights can sometimes be prohibitively expensive, so if the cost is reasonable, there's not much of a downside. It gives you a little more flexibility as well to change flights since it would only be impacting one direction.

Price would be the reason. Usually (2) one-way flights would be quite a bit more expensive than open-jaw options.

Go for it if you can afford it but two ways tickets are always grossly more expensive (twice the price or worse) with legacy carriers like Delta, United, and American Airlines for example.

Might be a glitch in the system. Try calling the airline to see if they can help.

We fly with miles and I always book one way at a time because it is easier—- I book each way as soon as the reward seats are released.

As long as the price is reasonable, I can think of no downside.

One caveat is that some countries( mainly outside of Europe, such as New Zealand) will require you to show that you have a ticket out of the country if you are flying in on a one-way ticket. In our case, this was checked at the check-in desk before boarding the flight. I was prepared for this and had a copy of our flight from New Zealand back to Australia 3 weeks later.

But I-have never needed this in our European travels. (not, for that mater, when we flew to Japan, or to Chile).

Are both of these flights on Delta or Delta partners? If they are and you are not seeing the flights via their website, try booking through an agent.

There are definitely some risks with doing this that you need to consider. In particular, it can be problem if you need to change your vacation dates and thus the dates of both tickets (e.g., you end up with 2 change fees). It can also be a problem if the airline completely cancels one of your flights and doesn’t offer you a satisfactory replacement and you end up wanting to fly on a different carrier. Some airlines charge substantially more for a one way ticket.

Yes, Delta or Delta partners, but I'd like to avoid ITA going to Italy, partly because it sounds like it's been a hassle to select our seats (a big deal to us) and partly because I worry that they are less reliable right now than Delta, KLM, Air France. Maybe I am wrong about both concerns?

Trip is this fall. I tried open-jaw on Delta's website, Google Flights, and Kayak to see if I got reasonable options, but what I'm seeing is a lot of ITA and a lot of super-short layover times like 1 hour and 5 minutes. That's what is making me wonder about trying one-way flights instead. For me, it's almost like a defeat to call an agent, but I may have to!

Well, we booked an open-jaw Delta flight that did use ITA. After putting in all our info, I hit purchase and was told that it would now cost an extra $200. So, OK, accepted that. Then tried to select seats on ITA, called ITA and they said it was impossible to pay more to select seats, impossible to upgrade our seating in order to select seats, and simply no dice except for 24 hours before the flight. Wait time to talk to Delta was going to be 2 hours, so we spent another $250 to change the ITA flight to a Delta flight. All kind of frustrating, but $1427 total each isn't horrifically bad. Sorry I chickened out of two one-way tickets --- I think it would actually have been a little cheaper.

Did you make the change within 24 hours of your initial purchase? If so, you might see if Delta will refund the change fee. They have a 24-hour cancellation period with no fee and you may be able to plead your case.

Yes, I made the change right away, as soon as my husband got the “two hour on hold” message from Delta —- I was happy to discover I could just change the ITA flight rather than canceling the whole trip and re-booking.

I don’t THINK there was a change fee, it was just a more expensive flight, but thanks, I will check!

On the Delta APP look for the Round Trip Pull down - there should be a Multi City option?