I have never found any over the ear phones to work on airplanes unless they are either noise-canceling or turned up excessively loud. I bought Bose QC15 phones. The sound isn't as good as, say Sennheiser HD600, but their nose cancellation is unparalleled and they are very comfortable. A little above your budget, but they work and they will save your hearing.
I agree. Bose QC15 will be the quietest, but sound quality will not be as good as a true audiophile headphone (they are a bit treble recessed (not sparkly) and boomy).
A passive closed headphone gives you the chance to get truly good sound, but at the expense of noise isolation. Here, the KEF M500 has been getting very good reviews.
Personally, I wont fly without IEMs. Period. You might experiment with different tips to find something comfortable. A pair of Etymotic HF5 would be my suggestion for superb sound and isolation. Etys come with a variety of tips so comfort is possible.
The airline provides me with Bose QC15's for international flights, but I never really cared for the sound given the expensive price tag. I wouldn't buy those, but they are comfortable and work well at blocking engine noise. Although it masks outside noise, I do tend to fixate on the ambient hum the headphones give out and that drives me crazy. I'll head to a few Hi-Fi stores in town to audition some headphones this weekend.