Booking two flights in one day
 

I booked two flights on the same day, BWI-DTW in October. (One leaving at 5ish, and one leaving at 8ish) WN had a good price for the ticket for both time slots. It's the "get-me-home" leg of a mileage run on DL/NW, and in case there are any bump opportunities, or delayed flights, I wanted to make sure that I could still get home, without having to pay more for standby or missed flight. I'll take the early one if I'm in BWI ontime, but I'll take the late one if I'm running late.

I know I can use the funds later for the flight I don't use, but there won't be any repercussions for doing what I did. (i.e. buying insurance in the from of two tickets) In all actuality, I feel kind of bad, since I took a cheap fare away from someone else.

This is not the end of the world, cfwolfs. Many of us, including me, do the same at times. Please cancel the flight that you do not need as soon as you know which flight you will take.

I do this fairly frequently as well.

It is allowable, so you are not doing anything wrong. Southwest is well known for this type of flexibility.

I've done it a couple of times, although usually for different days, (e.g. don't know if I'm going to fly back Wednesday or Thursday night). I do try and cancel as soon as I know for sure which flight I'm taking.

I do this frequently -- in fact, usually. It's the workaround for Southwest's perceived "disadvantage" (vs. other airlines) of having to pay the walk-up fare for any close-in change of a return. I'm happy to give Southwest the, usually, ~$50 float. Yes, I am sorry to take the low fare from someone else, but I think if they'd followed the same advance purchase and other t&c as me, they were eligible for the same low fare.

Are you sure? I thought that the SWA CoC specifically prohibited making speculative bookings.

It does, and I think multiple bookings were expressly forbidden . . .

Hmmm. I've not done this, myself. How late can one cancel a reservation without paying a penalty? (i.e. my flight is at 6; if I call at 4, can I still receive credit for the flight to be used later?)

You can no-show without penalty, nevermind cancelling. Another of WN's many advantages. :)

Here's the exact language:

You may not use the Southwest web sites to make any speculative, fraudulent, or false reservation or any reservation in anticipation of demand. If you have made multiple reservations to one or more destinations on or about the same date, Southwest reserves the right to cancel all such reservations without notice.

This surprised me a little bit. First, I don't think the OP's reservations were speculative, fraudulent, or false. Maybe they are speculative? However, I don't understand what "reservation in anticipation of demand" means. Maybe that's what the OP was doing?

Second, I didn't realize the T&C's threatened to cancel reservations. Has anyone had this happen?

I interpret that to mean booking with VDB intentions.

I suppose they are speculative... I mean, I speculate I'll be in Baltimore by 4pm, but if any of my string of flights are late (on DL, NW) that day, then I speculate I'll make it to Baltimore by 7. I'll know at the latest by 2pm that I'd cancel the late flight, or cancel the earlier one.

Don't airlines overbook on the speculation that people aren't going to show up?

On another note, what if I were to book a flight from DTW-MDW in the morning on WN, fly home on NW, then book another flight in the afternoon DTW-MDW. (Maybe I just really like to fly, which is true) By these rules, it would appear that WN would possibly cancel all of my flights. On or about the same date sounds like they could cancel a Wed/Thurs like ElmhurstNick was talking about.

I should clarify, I know what I'm doing is kind of wrong. I just am not sure how wrong it is...

Absolutely.

You're doing nothing wrong. The lack of free standby (absent "flat tire") on WN sometimes necessitates multiple bookings like yours. WN isn't losing sleep over it (they have your money, after all), and neither should you.

Some airlines are so unreliable that all bookings can be considered speculative. :p