chgoeditor

When thinking about destinations, you really have to ask yourself, "Is this a place people flock to at this time of year?" Optimally, you want to pick a destination with an abundance of hotel rooms and high vacancy rates at the time of year you're traveling.

So, for example, Florida in July or September is likely to be cheaper than Florida in December or March. New Orleans during Mardis Gras is more expensive than New Orleans in August. The fact that you're looking for winter/early spring is tough since warm weather destinations are popular and you have Christmas/President's Day/Easter/Spring Break holidays when a lot of people travel. But the flip side of that is that cold-weather destinations during these months also tend to be bigger cities which have less price flexibility in their rates if big conventions historically flock there during off season.

Is the time of year fixed in stone? I belong to an organization where members travel on their own dime and they've had a lot of luck with Memorial Day weekend in Dallas, Houston, Phoenix/Chandler, Atlanta and Los Angeles.