I fly Southwest whenever I can, and if they’re not available I’ll usually fly American. If you plan enough in advance, you can get some really decent fairs through Southwest. Also, I used to have to commute by plane between St. Louis and Kansas City, sometimes several times a week. Southwest was the cheapest, and very popular with commuters going between the two cities. It was also my company’s preferred airline. Most people who travelled had frequently flier miles which veryone in the company shared. So, if you needed to fly somewhere on business, you’d just e-mail people you knew who travelled a lot and they’d hook you up with a free flight.
That flight must take all of 15 minutes!
More like 45, but yeah - I spent more time in the airport than I ever did in the air. It was just plain silly. But, hey, at least I wasn’t paying for it! 
My mom, when she comes out to see us from AZ, always takes Southwest into Midway. Likewise, my brother, when he and his wife go to see her, they fly Southwest out of Midway - the airport is much more convenient than ORD, and the fares are usually around $100 - round trip. They’ve always been on time, never had a problem, etc. They swear by Southwest.
I used to fly on Southwest a lot more often before JetBlue started serving Oakland airport. I used to take Southwest to Burbank or Orange County to visit Mr Neville’s relatives in Southern California.
I flew on Southwest from Baltimore to Oakland a couple of times. It’s nice if you don’t mind stops, but you really don’t want to change planes. I was moving from Maryland to California, and had the absolute maximum amount of carry-ons and checked luggage that they would let me have- and this was before they restricted carry-ons after 9/11/01. My parents sometimes fly Southwest to come and visit us, since they are retired and the longer flight with all the stops doesn’t matter so much to them.
I’d say Southwest is best for short flights- Oakland to Southern California, Phoenix, or someplace like that. If you can get to Dulles, JetBlue is much, much nicer for flying from the DC area to Oakland. You still don’t get meals (of course, given some of the airline meals I’ve had, I don’t really count that as any great loss), but you do get DirecTV, and they have nonstop flights between Dulles and Oakland.
I think it was five days before the flight. I’m not sure how you can figure $100 to be a fair price for rebooking a ticket. How did they incur $100 worth of cost? And yes, I could have paid more for a fully refundable ticket, but that just means that I pay the $100 up front.
Anyway, the point is that on Southwest, I can cancel at any time and not have to pay any extra for rebooking the ticket. If I paid $300 for the ticket, I have $300 worth of credit, good for 1 year. In fact, I don’t even have to call and cancel my flight, I can just not show up, and it works the same way.
The last time I flew I wondered about this. I think it was United(?) from Denver to Dulles. Rather than having a meal included they were a la carte, about $10 for a meal that maybe cost them $5. I think about 15% of the people on the plane bought one. So I started to think about the profit they made on that. Assuming that there were 100 people on the flight, and they made $5 on the meal, then they made $75 extra by serving the meals.
Now, what if they served a meal to everyone on the flight and tacked on $5 extra on everyone’s ticket to make up for it. If they served a cheaper meal that cost them $3 (the a la carte food looked better than the usual airline food) and only made $2 per person, then that’s $200 extra they made, versus $75 if they provided the a la carte meals.
Obviously the airline figured the math differently, but it seems to me that you make more money by selling more meals. You just have to charge for the meals in the price of the ticket.
I fly SW whenever I have to go somewhere that they fly to. That’s because they basically own Islip Mac Arthur airport (only a few miles away), and their fares are so good especially at the last minute. Any other airline I have to go to JFK or LaGuardia or in some cases Newark, and they charge more.
Overall, I find their flights just fine. The longest trip I took was from Islip to Las Vegas, which was a “one stop don’t get off the plane” deal.
But if that extra $5 means just one less ticket sale, then the $125 difference in profit is wiped out and more.
Well, you’re trying to book around the Christmas holidays - naturally the good deals would disappear fast, like as soon as they’re available. For lower-demand time frames, the cheapest fares are often readily available. Heck, a few weeks ago, I booked my daughter on Southwest from Orlando to BWI for Thanksgiving and I got the second-lowest fare - right around $200 including all their silly fees. And it is a non-stop flight.