Better "Noise Cancelling" Headphones for Air Travel?

Full disclosure, I know next to nothing about headphones. I own a few pairs of ear buds and a pair of Bose noise-cancelling headphones for air travel and cutting the lawn. However, I have an upcoming international trip with my wife that seems a great excuse/opportunity to upgrade to a decent set of headphones. My wife won't care if she get the new set or the old, we can't both use the one pair, and it's a long flight.

For the trip, I'll be pairing my headphones with an iPhone/iPad & Dragonfly Red DAC that I already own. Budget is flexible but I'd don't want to go crazy...I'll probably spend <$500 but don't mind if people discuss other options within shouting distance of that amount to generate conversation.

My questions are:
1) How well do passive noise cancelling audiophile quality headphones cancel out the constant drone of a jet engine?..specific recommendations for those that would do it well, if any, appreciated

2) With that much background noise, are higher quality headphones even worth it or would I only notice the benefit in a quiet environment?..I'll probably stick to sharing my music with the family when in my own home so these aren't going to get tons of use outside of traveling.

3) Any recommendations for a pair of active noise cancelling headphones that sound better than Bose (QC35s) with the active noise-cancelling feature engaged?

Thanks in advance!
Best of breed : Master & Dynamic ....,. take your choiice, on-ear, over-ear, or in-ear monitors ( it's a personal comfort choice) 

go the website and check out the links to the bevy of "best" reviews 

I have the MH-30s with the AQ Dragonfly . It bests my other pair of Beyerdynamic T51i's, that are fine units in their own right.

Sir Paul McCartney apparently bought a boatload of MDs for himself, his band,  and full  entourage.

Rather than go for active noise cancelling headphones (all of which mess up the sound to some degree) why not go for in ear monitor type headphones (the type which stick into your ear canal and significantly block out outside noise)

Assuming you can live with this design (some folks hate them) there are loads of different options available at all sorts of price points. I use Shure SE535 which work great on my long haul flights and can definitely appreciate the quality of this set over some of my cheaper alternatives. There are lots of different suppliers and you can find a range of options that fit your budget here

If you do prefer to go with active noise cancelling give the folks at Echo Audio in PDX a call, they take the time to find the best at different price points and I bought a pair of Sennheisers from them for my wife (who does not like in ear) which she finds work well
The best IEM is the Shure SE846. It is better than anything else for your application. Forget about cancellation nonsense and enjoy 37dB noise reduction with the memory phone buds.
Glad I asked. In my naivity, I had presumed that bigger over-ear style headphones would have more material to block out the sound and do a better job for me. Clearly, thats not the case and the IEMs are also going to take up a lot less room in a carry-on. Thanks guys.

I'll read up on the Master & Dynamic in-ear & the Shure.
Etymotic.....   works well with the Iphone, etc.
let me help you on this, i spent a good time finding my own bose wireless speakers, they are the best, you read these two guides about wireless portables speakers i hope these guides will help you.

please dont hesitate me to ask any question about them, i work in a media studio. thanks
I fly over 100,000 miles a year and can't wear over-ear phones because they press down on the sides of my glasses and hurt my ears if I wear them too long. After trying multiple offerings I settled on Beoplay H8  on-ear phones ( which do a resonable job of noise cancelling but are a huge improvement on Bose for sheer musicality.
My local dealer (HiDef Lifestyle) also said to look at Fiil Canvas if you need a cheaper alternative (
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Audio Technica ATH-ANC7b
When I travel I can't deal with the bulk and pressure from over or on ear headphones as I get sinus troubles during travel on dry planes. For a while that meant no noise canceling for me, but now that may change. I am closely watching Bluetooth 5 specifically the new Qualcomm chipset. It's not widely available yet but once it is there will be some pretty advanced ANC included. More on that here:

In the mean time I go for cheaper earbuds that actually make a good seal in the ear, which does have a pretty substantial noise canceling effect when on the plane. There's a pretty good list on the same site as the guide I linked above here:
Any Shure IEM with the foam tips, properly applied, are the best,
You have to go through the ritual though. Squeeze the tips with your fingers, hold them in while pulling up on your ear. This ensures the best noise blocking and bass response.

They used to use yellow foam, which was much like you'd buy for construction work, but they are high maintenance. The black foam tips are about as good but last longer.
Over the ear are by far the best in quieting down the noise, which really reduces flying fatigue. Bose and Sony’s (the new models) are best. I own Bose specially for air travel, and others for at home for sound quality. Better to buy for them specifically for each purpose, rather than trying to combine the two objectives. The Bose 25s are under $200 now, all you need. 
I have not heard noise cancelling phones that deliver decent sound.  I would go the route Erik Squires recommended--good in-ear models.  They deliver great sound and do a terrific job of cancelling noise.  Some models can be a bit uncomfortable; if you are serious about in-ear models, you can get ones that offer custom-molded insert pieces that are made from an impression taken from the listeners ear by audiologist that fit hearing aids.  

The model of in-ear phones that I use comes from Etymotic.
I’ve been using active noise cancelling for a long time. Aside from the electronics, a major part of the noise reduction is the physical blocking of noise from covering the ears (and the padding around the ears). In-ear, regardless of quality, just don’t work as well in quieting down the ride...which is the primary objective. And remember that on long flights you’ll use them for sleeping, and over ear are much more comfortable. 
I have Bose QC 25's and they are excellent at eliminating ambient noise inside an airliner. My wife wears them without any sound input, personally I have to have music. I can't stand the noise on the plane, but with these it's 95 percent gone.
If anyone is interested here is the link with my selection of headphones for 2018 and a comparison of their characteristics
I hope someone will come in handy