My favorite win-a-trip story is Continental Airlines had a booth at some kind of college student trade show in Boston sometime around 1991. (Attending vendors were those interested in pitching their merchandise [free samples, coupons, etc.] to college students....) I can't remember the exact details, but for $5 (which would go to charity), you'd get 3 bean bags to toss through a carnival-style clown face with holes cut out. If you got all 3 through, you won a voucher for a 48-states round trip ticket! I wasted no time in digging out some cash, and it took something like $20 to win 2 vouchers. The employees working the booth didn't mind having me win the second, but waved me off before I could try winning even more.

Sweet deal.