Should i book or not?

[moesy4]

We are planning to fly SWA for a trip we currently have booked April 30th- May 8th, 2016. We have the room booked and tickets purchased, but it is fully refundable up to 5 days before. We are set on going on the trip, but haven't saved up quite all the money yet so there is a small chance we would have to cancel due to that or some other reason.
We will have enough SW points to book all our flights in about 2 weeks. We also have a $200 LUV voucher that expires the first week in May.
I am also taking a flight to New York to visit my friend....dates are flexible but sometime in the next month or two. Trip is a sure thing (MIL gifted us the LUV voucher so I could go).
Anyway, I have been watching flights and the ideal time (nonstop, middle of the day) has opened up for flying down there at the lowest price I've seen. I have enough points to use that plus the LUV vouchers to book now. I could then book the departure and the flight to New York in two weeks when we get the rest of the points. If for some reason we have to cancel though, the LUV vouchers would essentially be wasted as I would probably be back from New York then and the expiration stays the same if I were to cancel.

Or...I could book the flight to New York with the LUV voucher to guarantee it gets used, wait to book all flights until we get the points, etc. I think I could get the same price flight in two weeks, but not the ideal time (would either involve flying out at 7:30 am with a 1,2, and 6 year old or not arriving until after 5 pm).

 

[Donna M]

Why can't flights just be a given price with no magic ball needed? I hate having to be the situation you're in.

 

[mousehockey37]

If you have your ideal flights now, it's go time to book them. Don't wait because if you do, more than likely, you're stuck with whatever is left at whatever the price is. I understand there's a bunch of variables in play, but flights are a pretty big one as well.

On a side, why would you go through everything if you willingly know there's a chance you could cancel (I mean, most of us when we make the reservation are sure we're going barring a catastrophic event)? Is there any way to get any OT or anything to help as far as saving up goes?

2 weeks is a long time for prices to go in different directions.

I know we all handle paying for our vacations differently, but I'm kinda lost that you're still up in the air if the trip is going to happen.

I'd say if you're 99.9% sure it's a go, then book everything. Use the voucher for NY but get the other flights booked now.

 

[moesy4]

It isn't necessarily the cost factor, I'm pretty sure we could swing it no matter what...it has more to do with the fact that my DH is semi looking for a new job so if there are sudden unrelated expenses to that or if he isn't able to get the week off, it could change things.
We ended up booking the flights as it was literally the only one that wouldn't interfere with wake up time or nap times so it's our best chance of starting off the trip on the right foot .

 

[moesy4]

If you have your ideal flights now, it's go time to book them. Don't wait because if you do, more than likely, you're stuck with whatever is left at whatever the price is. I understand there's a bunch of variables in play, but flights are a pretty big one as well.

On a side, why would you go through everything if you willingly know there's a chance you could cancel (I mean, most of us when we make the reservation are sure we're going barring a catastrophic event)? Is there any way to get any OT or anything to help as far as saving up goes?

2 weeks is a long time for prices to go in different directions.

I know we all handle paying for our vacations differently, but I'm kinda lost that you're still up in the air if the trip is going to happen.

I'd say if you're 99.9% sure it's a go, then book everything. Use the voucher for NY but get the other flights booked now.

Oh, and also, we're dependent on this credit card bonus as part of the travel expenses, otherwise we would just be picking a less expensive vacation. We should get it no problem as we meet the criteria, but I don't want to assume it's going to show up in 2 weeks and then some snag is hit and it doesn't. We are a one income, budgeting family and saving up CC points is how we afford to vacation as we use our "regular" money for household stuff!