Depends on where you're based out of.
There's a great site up in Toronto that with about 3 weeks left before the vacation would starts buys all the left-over packages that the charter companies have. They pay maybe 10 cents on the dollar price-wise and buy what-ever is left over, be it 2 seats or 20 seats. With 3 weeks left before the trip starts they sell the trip at 50% of the charter company price. With 2 weeks before the trip leaves they sell the trip at 40% of the charter price. With 1 week left it goes down to about 30% of the charter price, and the day before you can get it at their cost, which is about 10% of the original price - at that time all they want to do is break even.
This gives you some AMAZING values, however, and the big however, is that you don't know what trips will be for sale until shortly before you actually go. If you don't mind going "to somewhere warm", regardless if the place is Cancun, Cozumel, Aruba, Dominican Republic, etc, this is a great place to shop for a trip.
If you're the planning type that has to have everything scheduled or the world will come to an end stay away from this place.
I've purchased from them 4 times. My parents (when my dad was still alive), purchased about 20 trips from them. Never had a bad experience. Like I said though, you gotta be willing to go anywhere.
Cheapest trip I had was I purchased a week in Acapulco the day before the trip left. My parents and sister had already booked the trip about 10 days out and paid about $600 each for the trip (hotel + air, not an all inclusive resort). I paid $250 the day before. Had the exact same flight + room type but because I waited got a much better deal. Nicest trip I took with them was to the Barcelo Maya Resort along with Mayan Riviera (south of Cancun). Wife and I went over Valentine's day the year after we were married. All inclusive resort, and I mean it's a resort - just a stunning place to go. We got airfare, hotel + food (tips were included also) for around $650 USD per person. That trip was the most relaxing trip I have ever been on. We got to the hotel and did absolutely nothing for an entire week except eat, drink, lay on the beach, have sex and sleep. We were getting up around 9:00am and going to bed around 9:00pm. Just an amazing trip.
They do a good job of saying if the hotel they have is a 3 star, 4 star, 5 star or resort, and there is a BIG difference between a 3 star and resort, but like I said they're very good about identifying the property.
PM me if you want the contact information for them. Like I said they've got great deals but it's for leaving out of Toronto.