We haven't done a last minute trip for quite a while, but whenever we need a quick week or two away, we like to book at the last minute. The main benefit is that you can get a great price. For example, today you can book an all-inclusive trip to Varadero, Cuba from Toronto for $435 CAN per person and that's TAX INCLUDED. That's your airfare, meals, hotel, and drinks...all included!
We've found that the best deals are usually out of Toronto...but deals out of other cities do come along. And, the best deals usually involve one of three destinations...Cuba, Dominican Republic, or Mexico.
These types of cheap vacations normally involve a hotel property that is rated at 3 stars or less. However the better properties also come on special if you're willing to pay a little more. We've found that we have just as much fun staying in the cheapest place. You're only in the room to sleep, so we never cared if it's fancy.Here's a couple of the better last minute websites... http://www.pricebeat.ca
These guys have great last minute pricing, with a bonus. You get a free gift card with every trip booked. The value of the gift card depends on the price of the trip you book. What a great bonus!
This site usually has the best deals on last minute flights. Yesterdays deal (now sold out) was a flight Toronto to Cancun for $58 plus tax, return. Now that's about $300 CAN with the taxes in, but the only way to get a deal on taxes is to move out of Canada! Still, it's a good deal for flight only.
When you're on the hunt for the best deal, don't forget to check these sites 3-4 times per day. The deals can change quickly, and they can also sell out quickly.
And the other thing to do is sign up for http://www.travelzoo.ca in Canada, or http://www.travelzoo.com in the United States. Once a week they will email you a list of the best travel deals to be found on the web.
We love to travel last minute, we have a great time, and it doesn't cost very much!