I think this Farecast tool does exactly what you want.
Choose your originating city and it’ll list flights to all sorts of places, showing you the price of the cheapest dates to fly within a 30 day period. You can narrow it down to a specific destination city as well.
First of all places like Orbitz and Travelocity aren’t scams but you have to read VERY carefully.
You might want to try Priceline or Hotwire, you have to read even closer there.
For instance, these sites often say “Alternate Airports,” and check it to begin with.
I wanted to go from Chicago to New York. At the time Orbitz, Priceline and Travelocity were listing Milwaukee and Philadelphia as “alternate” airports to Chicago and NYC. So you if you didn’t look you could book a trip from Milwaukee to Philadelphia thinking you were going from Chicago to New York City.
Also you have to look at dates. These places sell the fares that couldn’t be sold anyway. So you’re probably not going to get great flight times, 'cause the airlines can sell them for much more to businessmen.
So if you want five days you could book a flight leaving Monday coming back Friday.
So you could leave at 11:55pm on Monday and have to return on 12:05am Friday. That is really only Tues, Wed and Thurs.
When you get to the hotel remember the hotel is giving you a discount rate, so they are gonna give the Orbitz or Travelocity visitor the worst rooms. For instance, the ones near an elevator, or facing the air conditioning system and you can’t upgrade them. If the hotel is oversold you’ll be the first to be walked, as the hotel has already gotten paid for the room.
The problem is in the Winter the warm places will most likely be peak and won’t have anything to sell cheap. You might want to try warm areas that are not at the beach or not touristy
You CAN work the travel sites but READ VERY CAREFULLY and THINK about what they are asking.
Well, www.travelzoo.com should still be doing crazy, last-minute stuff like ‘Fly to Paris this valentine’s Day weekend! Round trip airfare and hotel for $250!’
It’s pretty sweet. Part of our honeymoon was 6 days in Ireland, with the round trip from the US, the rental car with unlimited miles, and lodging each night for $500 each.
Just check frequently for what’s going on and stay flexible, and it might work for you.
Cancun - unless you really like overdeveloped tourist areas, I recommend looking at some of the outlying areas. Playa del Carmen and Cozumel are both somewhat better. The last time I was there (and by last, I mean, I am not ever going back to the Yucatan; my parents really like it and I’ve been dragged there on dull family vacations enough for one life) we stayed in Puerto Morelos. It was a VERY small fishing village in 1998. My parents thought it was heaven - an empty beach and nothing to do. My sister and I nearly died of boredom. I’m not sure what it’s like now.
The point is: you can probably do cheaper (and almost certainly stay somewhere nicer) if you leave Cancun itself.
Another vote for http://www.kayak.com. It’s very good, but it takes a little time to learn all the features. It’s consistently found me cheap flights that would have taken hours to find any other way.