Hi. I’ve never booked my package first and then flights, but we are doing that for our Summer 2020 trip. I just randomly picked a date starting with July 7 for the trip. We’re both teachers, so summer is open. We were looking at the Southwest site and noticed the points for this July. Really high for the third day after the Fourth of July and then goes down the week after that. I wasn’t even thinking about that. That’s probably a bad time to choose with people flying back from Fourth of July trips? I think I’m going to ask my agent to make a change. What do you think?
I just checked my August SW flights to make sure I am giving you the correct info.
No, I would not change my dates. Are you booking with points? I booked my SW flights on opening day ( that is my general rule). My August dates opened at two separate booking times. For my flight down I booked opening day one-way cash. When I just looked the flight now costs twice as much. A couple of months later I booked my return flights on points. It was about 12,000 for each tickets. A couple of months ago it dropped and I got almost 10,000 points back. Today it is almost 18,000 points per ticket.
Book on opening day!
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I agree-- book on opening day and you should be fine with most any date. I would think the 7th would be better next year as well since it’s on a Tuesday, so likely not as popular.
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We will book with points. We’ve always flown using our Southwest Points and will book on opening day. I just was wondering if choosing dates that close to a holiday is a bad idea if you have the option of choosing any dates. Are those dates almost always going to take more points?
That’s why I originally picked that date. Somewhere in the back of my mind, I was thinking that Tuesday is said to be a cheaper day to fly.
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I think you are right.
Flying real close to a holiday can be more expensive, but at this point you’d have to consider what else you’d pay more for or lose out on if you change. I always just plan for the dates I want, book the flights after I know what my dates are, then watch every day to look for lower fares. If possible, book each person on each one way ticket separately, that way if only one lower fare is available you can get it. My best ever was a $29 fare. I think it was around 1800 pts.
So to answer your question, I’d keep my dates but consider changing my flights plus or minus a day if i could save a lot or get a free vacation day (flight savings cancels out extra hotel night).
I would watch & price out different flights on different days of the week. In my experience, except for the actual holiday or day before/after, the day of the week impacts price the most. For my airport, Tuesdays & Wednesdays are the cheapest 99% of the time, so we planned accordingly. Saved us over $50pp by doing so.
It is.
I love, love SWA, but they really stuck it to me for my upcoming Thanksgiving trip — $700+ per ticket. I have a family of 4 so it was over $2900 total:flushed:. UA which also has direct flights from Houston was over $800/ticket. I hate being a slave to the school calendar. 
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Keep checking the price of the flights and get an adjustment. I had the fly Thanksgiving weekend once and i booked opening day. Then sometime later saw a post here or in chat to check the prices and saw li ke $300 difference. I called and got an adjustment
It is worth continuing to check your flights. Just like car eentals book and keep checking for lower rates.
Love it here I have learned so much
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Good idea.
So wouldn’t it be better to switch to the next Tuesday and give myself a buffer from the holiday? I could switch from Tuesday, July 7 to Tuesday, July 14. We just have the three day hold on the package now, so it shouldn’t be a big deal. Also, how do you know when the opening day of flight sales begins for Southwest? Do you just start checking daily about six months out? Sorry for all the questions. I’m just used to booking cheapest flight and then picking dates. This planning a year out business has me all messed up!
They post the opening date on their website 
Why do you need to make that change now? Can’t you wait until after you see the opening day prices?
I could. I was just going by what my new MVT agent said. She advised booking our package now because some resorts and rooms are selling out for summer 2020 already. So I just quickly, randomly gave her a date.
She doesn’t have a deal for any summer dates yet, does she?
No deals at this time. She said to book now, and when/if deals come, she will then modify. She said that some resort categories and dates are already selling out for next summer. My email said that there are no offers available at this time for 2020 but MVT clients will be the first to have any offers added to their reservations when they become available. That’s why I booked now instead of waiting.
Have you checked to see if any resorts (other than villas) are not available ?
I’m booking French Quarter. This is my daughter’s graduation trip, and that is her first choice. I did say that I would consider a different resort if it has a good deal. The agent told me no deals yet this far out.