Has anyone done this? I’ve been researching flights. I originally thought I should wait until closer to travel (January 2020) but I’m worried that I might shoot myself in the foot if I do that. We really REALLY would like to fly direct (PIT - MCO) if at all possible. Southwest has currently released schedules up through Jan 5, which covers our departure but NOT our return.
I’ve priced other airlines, and as of right now, prices that LOOK lower really aren’t, due to (a) baggage fees, and (b) wanting to preserve the change/cancellation option. And nobody offers direct except for SW or Spirit. We have done spirit before, but they are more than SW even before baggage fees, at least if I book now. Flying direct is definitely worth some added $$$ to us, especially since it lessons concerns about weather delays/missed connections (flying out of PA in January, this is a real concern).
So I’m thinking I want to lock in our departure flight as a one-way now, and then watch in August when they will release the schedule and I can book our return. Why am I so scared to lock anything in?? 
lol
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I have not tried this in particular, but I don’t think it hurts to try it? Even if it ends up being cheaper to book the two-way flight, they will credit you the amount you paid toward the flight you change it to. I have always flown SW and to me, they have always been super easy to work with even when making changes.
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I only ever make two one-way reservations. T
It makes it much easier to modify legs if you need/want to.
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Also Southwest allows you to cancel at no cost and holds the funds for future travel. And any and all changes are fee-free
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I often book one way with SW. My trip in 8 days was booked on opening day- two different flight openings. My next booking will be cash one way, points on the return. I am booking points on the return because I might extend my trip by one or two nights and I like to make those changes with points.
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As long as the cost of two one ways is the same as the cost of a return, you should be fine. You can test this with trying to book flights with fake dates that are already showing.
FYI, Southwest had a note on their site that the next round of flights will be released on Aug 15. It was supposed to be July 30 (as of 6 weeks ago when I checked), but I guess it was moved.
So if other people are waiting for that return flight like you are, maybe getting a jump on them by booking the one way is a good choice.
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We did this last trip s I ncd returns were not open yet. Worked great.
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Thanks, everyone! I did pull the trigger on the departure flight! I know that SW allows changes and I can get a refund “voucher” if the price drops. We don’t travel enough to make it likely that we would use a voucher within 12 months, but that could make this even more strategic. If by chance our departure drops in price BEFORE I book our return trip, I could use the voucher on our return! I’m relieved to have the departure locked in.
I told dh, “I booked our flight to Disney, but not the flight home. So we might just have to live there!” 
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I did that for upcoming October Disney trip. I recall a $49 sale had one of the flights at a price that couldn’t possibly go lower. I booked it at that time and then booked the other a week or so later. All should be well.
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Do you know if the next release will include next June, or how far out it goes?
The august 15th release is set to open dates thru March. I have read that once those are released SW will set the next release date which hopefully will extend into June.
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