When do you book your flight?

PoppyJ

Mouseketeer
Joined
Mar 24, 2022
I'm curious about how others plan their trips because I'm struggling. This is actually the first trip that I'm planning that has slightly flexible dates.

I want to go for Festival of the Arts next year. I'm thinking early February so my booking date is coming up.

I can't decide whether I should book Saturday-Saturday; Friday-Sunday; Wednesday-Wednesday; or something else...

I'm trying to look at flights to see what the cheapest option would be but flights are not out yet!

The easy answer would be to book something now and modify once we decide on flights but I know our preferred room (BCV studio) will not be available for too long after the 11 month mark, so we'll have to work with what we book now. (Although the pool will be closed for refurbishment so maybe we will have some flexibility??)

Got me thinking I can't be the only person who struggles with this, so how do you book your trips?!? When do you book your flight relative to booking your room?
 
I pick my dates for the trip and then buy the plane tickets. I also usually go for a week at a time due to my kids' school schedule. Occasionally we drive, but usually we fly since I don't like being the only adult driving for 10 hours.
 
Sometimes, there is something to be said for a Wed-Wed trip, or a Tue-Tue trip. We have found at times the airfares will be better. What if you look at the equivalent flights perhaps in mid-Jan? Might they offer a slight clue regarding the cost differences? Of course, if you go back far enough in Jan to check, you might run into the MLK weekend, so it wouldn't be a good comparison!

In reality, if you want BCV for a week, I'd select the days you want, book the room, and then get that airfare. The points go up just a little bit Feb 1, so Jan reservations sometimes are a little more popular. And you're also correct - without the big pool at BC the first few months of 2025, it might impact some plans for folks. But FOA is definitely worth it!! Our favorite festival. Good luck with your planning....
 


I'm curious about how others plan their trips because I'm struggling. This is actually the first trip that I'm planning that has slightly flexible dates.

I want to go for Festival of the Arts next year. I'm thinking early February so my booking date is coming up.

I can't decide whether I should book Saturday-Saturday; Friday-Sunday; Wednesday-Wednesday; or something else...

I'm trying to look at flights to see what the cheapest option would be but flights are not out yet!

The easy answer would be to book something now and modify once we decide on flights but I know our preferred room (BCV studio) will not be available for too long after the 11 month mark, so we'll have to work with what we book now. (Although the pool will be closed for refurbishment so maybe we will have some flexibility??)

Got me thinking I can't be the only person who struggles with this, so how do you book your trips?!? When do you book your flight relative to booking your room?

I have this exact same dilemma every year. Festival of the Arts, BCV studio, flights not out yet. Fortunately I have enough BCV points for about 9 days in a studio, so I book that and then. when the flights come out, I just cancel the ones I don't want. Also I consider what day I'll get there-what I mean is that I would want to go to the FotA the very first full day. So that means getting there on Friday is a bad idea (weekend crowds). I know that if you're looking at Southwest, in the last few years, I've found that flying to Orlando Mon-Wed have relatively good prices, as do flying home on Wed-Sat. For some reason, Sundays are usually more expensive.
 
Southwest - when they release fares. I typically book on RR points (I have the Visa), I check periodically. I got a 2,000 point refund this week on my 4/28 flight.
 


Airfare from my area to/from Orlando is usually cheaper Tuesday to Tuesday or Wednesday to Wednesday. So I book the room.and since I generally stay in 1 bedroom or larger units, I can re-adjust if necessary when Southwest releases the fares.
 
This is one of the main reasons we don't fly Southwest anymore. Their fare release schedule sucks and doesn't work with the advance planning I like to do around work and school schedules. So I'm usually booking JetBlue right around the 11 month window when I'd be booking DVC.

(Though, to be fair, the lion's share of my DVC points are Aulani so more often than not I'm booking WDW at 7 months, not 11. But we like 1BR so availability is rarely an issue.)
 
Yes, I know its backwards, but we normally book airline first (find the cheapest flight) and then plan the trip about flight.
With the 11 month booking window id find it hard to believe airlines would even have a scheduled flight to book. lol
 
This is one of the main reasons we don't fly Southwest anymore. Their fare release schedule sucks and doesn't work with the advance planning I like to do around work and school schedules. So I'm usually booking JetBlue right around the 11 month window when I'd be booking DVC.
I was very bummed when JetBlue pulled out of my local airport. I had just got my new JB credit card & they used to fly everywhere i needed. :(
 
With the 11 month booking window id find it hard to believe airlines would even have a scheduled flight to book. lol

Again, backwards, we book whatever disney resort is available (but again, we only go about 3-4 days at a time). If you plan on Wed or Tues depart and return (avoiding holidays) you should be fine.
 
Thanks everyone for your comments/ideas/suggestions!

I've been playing around with flights. Unfortunately, the only airlines that fly direct to MCO from my airport are Frontier and Breeze Airways, and both release their schedules later than the bigger airlines AND both only fly on certain days.

So looking at American/Delta/United with a layover, flying Wednesday to Wednesday is typically about $200 cheaper than Friday to Sunday (with a full week between).

So the sensible side of me says book Wednesday to Wednesday. But then I thought, that's 6 days of vacation to take off Wednesday to Friday, then Monday to Wednesday the following week! If we go Friday to Sunday, my husband can flex Friday, not take any vacation time, then take 5 days of vacation the following week. But that also means more expensive flights, additional cash to book additional days because I don't have enough points and additional expenses during the trip...
 
Thanks everyone for your comments/ideas/suggestions!

I've been playing around with flights. Unfortunately, the only airlines that fly direct to MCO from my airport are Frontier and Breeze Airways, and both release their schedules later than the bigger airlines AND both only fly on certain days.

So looking at American/Delta/United with a layover, flying Wednesday to Wednesday is typically about $200 cheaper than Friday to Sunday (with a full week between).

So the sensible side of me says book Wednesday to Wednesday. But then I thought, that's 6 days of vacation to take off Wednesday to Friday, then Monday to Wednesday the following week! If we go Friday to Sunday, my husband can flex Friday, not take any vacation time, then take 5 days of vacation the following week. But that also means more expensive flights, additional cash to book additional days because I don't have enough points and additional expenses during the trip...
How much do you value the direct flights? For us it is a game changer to only have to go through loading onto the plane once with DS.

We also have SW so we know they will fly everyday.

Any way to check what days Frontier and Breeze flew that time of year previously? It may give you an idea on the days to book.
 
How much do you value the direct flights? For us it is a game changer to only have to go through loading onto the plane once with DS.
Personally, I would definitely pay more for a direct flight, but there aren't any close to me, & I'm not willing to drive way farther (both ways) for the direct flight which includes paying more.
 
How much do you value the direct flights? For us it is a game changer to only have to go through loading onto the plane once with DS.

We also have SW so we know they will fly everyday.

Any way to check what days Frontier and Breeze flew that time of year previously? It may give you an idea on the days to book.
I definitely value direct flights, but they are making it really difficult. Really undesirable times... Fly out on a Saturday at 8:00 pm and get into MCO at midnight. Who wants to waste their entire Saturday?? Then fly out of MCO at 6:00 am. Ugh, I've seen those pictures of security lines in the morning... But it's definitely cheaper, and I think for a week long trip we could do just a personal item.

I wish we had Southwest!
 
Personally, I would definitely pay more for a direct flight, but there aren't any close to me, & I'm not willing to drive way farther (both ways) for the direct flight which includes paying more.
Same! I wish we had more direct flights. We have two airports that are about a 2 hour drive that have a lot more. The past couple years we have been driving, but we're getting fatigued from the drive so we're going to pay a little more for a flight out of our airport and save on the gas/hotel.
 

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