I have not flown as much as Jan or some of the others

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so they might have more specifics on that. Remember too that if you use Kayak, as someone else mentioned, or any other service like them (Expedia, Hotwire, etc.) that they won’t show Southwest. SW does not list on them.
Be sure you are comparing apples to apples …. same day or date for flights, same amount of baggage, same airfare class, etc.
Oh, sometimes taking a very early flight such as 6:00 AM or a red eye is cheaper than leaving later in the day. I would suggest you be as flexible as possible with your dates to get the best rate. I checked flights on Southwest and pulled 2 dates out of thin air … Leavng from Seattle (couldn’t remember if that was right) and flying to Midland, was a little over $1800 for 4 with only one layover. That was leaving on 4/12 and returning on 4/20. It is a little better I think than what you found but I am fuzzy on the prices you quoted in a previous email.
It doesn’t sound like driving is a possibility from what you said and that flying can be, especially if you do not have to pay for lodging once you arrive at your destination … if you can find the right price. Just keep looking and I believe you’ll come up with a flight plan that meets your budget.

Check rates

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on Kak.com, especially on Tuesday and Wednesday mornings when airline rates are the cheapest, and then keep checking. If you’re brave, you can try the Name Your Own Price option on Priceline. The problem is, you can have a number of connections and it might be terribly inconvenient, but the price may be right. I use this option to book hotel reservations each week for my sales staff. I don’t have many qualms about doing this because I choose a star rating, or I use Corporate Lodging Consultants to book their hotel stays, but the Name Your Own Price option on Priceline is generally cheapest. I generally go the Kak route for airfare, but if you do find a great rate that way, do call the airline then and book the reservation directly there with them. I have been given upgrades on flights solely because I booked with the airlines themself and not with a discount online booking site.