Going to the airport and hopping on a plane is definitely a thing of the past. These days you're likely to be charged 5x the normal ticket price. I've had several airline reps tell me straight up "If you're buying a ticket last minute, odds are you really need it, so the airlines charge more knowing you will still pay".
Seldom do you see all inclusive last minute deals like you used to. You can get lucky though, and if you're like A790 and can come and go as you please, then you will have more luck. But booking a few months in advance seems to always be the cheapest way.
I'm a big fan of heading south for the winter, so over the years I've kept pretty good track of prices. Take it with a grain of salt, this is just my experience.
Originally posted by Isaiah
Chris Myden suggested farecompare which is an aggregator for all the online sites so you can compare all on one place.
I actually find that his website is pretty good for finding deals. Between him, redtag, and itravel, all your bases are covered.
I can eat more hot wings than you.