You don’t want to miss out on the five best headphone deals of October Prime Day, ending soon

Hear me out—here are the best ways to save valuable time when deciding where to spend your valuable funds. I’ve looked at all the deals during Amazon’s October sale (aka Prime Big Deal Days) and picked out the best of the best buys for personal audio enthusiasts. But act fast; these deals will be done when the day is. (Prices are correct at time of posting but subject to change, and deals can sell out, so add to cart quickly.)

Sennheiser 660S2 Audiophile Hi-Res Open-Back Dynamic Headphones $381 (Was $599)

Looking for an expansive listen with an expressive midrange? You’re going to need wired headphones, and you’re gonna need these headphones. Sennheiser is one of the first names that come to mind when discussing reference-level headphones with low harmonic distortion. Introduced in early 2023, the Sennheiser HD 660S2 is a retooled, bass-reinforced revision in the German audiophile brand’s long-running series of headphones for exploring the silkier parts of the sonic spectrum. The soundstage is wide but precise but now extends into even more dramatic depths—with sub-bass reaching to 70Hz. While the open-back build means there’s no isolation, it also contributes to a toned sense of imaging, making these excellent headphones both for fans of musicality and musculature—the kind of comfortable, masterful set that is as good with heated gaming as it is hot tracks. (If you’re looking for a darker, richer response or a closed-back option, Sennheiser has several other top-tier models on sale.)

Bowers & Wilkins Px8 Over-Ear Noise-Cancelling Wireless Headphones $426 (Was $699)

Perfect for on-the-go audiophiles, The Bowers & Wilkins flagship Px8 wireless headphones feature bespoke 40mm carbon cones—derived from the B&W 700 Series loudspeakers domes—that are coupled with an optimized basket/motor system. This tilts the sound signature from body blows to landing right on the button. Separation and control are heightened and tightened, tempering unruly transients that can come across as excitement but threaten to trip up accuracy. Angled to attain a uniform alignment between every point of the ear and driver surface, these light-yet-rigid carbon cones are intended for low-distortion (THD+N <0.1%), high-engagement listening. Most impressive is that this precision-engineered spacious audio is available wherever and whenever you need it, using Bluetooth 5.2 for a solid connection with support for the SBC, AAC, and aptX Adaptive (with aptX HD) codecs for maximum iOS/Android compatibility. (Want some B&W sound for less? The Px7 S2e is still expressive while more affordable.)

Bose QuietComfort Ultra Wireless Bluetooth Headphones with Spatial Audio $329 (Was $429)

Bose’s QuietComfort Ultra headphones have the best active noise cancellation of any over-ear model we’ve tested, and these headphones are at their lowest price ever. Whether you’re trying to drown out the sound of overzealous friends and family members at a gathering or focusing on getting rest during plane or train travel, these headphones will be your constant, cherished companion during the hectic holiday season. The QuietComfort Ultra is the latest in a long line of Bose headphones that push the boundaries of ANC performance. In our experience, these headphones can eliminate the sound of the New York City subway when listening to music and should do an equally impressive job for plane engines and sidewalk construction. The headphones’ noise cancellation is complemented by 24 hours of playtime per charge, support for Immersive Audio, a multi-mic array for calls, energetic audio quality, and ample cushioning on the ear cups and headband. These comfortable, comforting headphones are worth their usual price, but Amazon’s current discount makes them an even better get. (Prefer the same trusted Bose ANC algorithms but in earbuds? Those are on sale, too.)

Denon PerL Pro True Wireless Earbuds w/ Adaptive Noise Cancelling & Personalized Sound $195 (Was $299)

OK, so these aren’t headphones. But some people think cucumbers taste better pickled. Anyways … The Denon PerL Pro True Wireless Earbuds use something called Masimo Adaptive Acoustic Technology to generate an EQ based on the user’s inner ear activity. That’s why it’s called the PerL, for Personalized Listening. And, having tested it, I can confirm it really works to add some raw power and sense memories back into songs and ears somewhat dulled by time. Delivering this are distinctive 8.6g disc-shaped housings with 10mm triple-layer titanium diaphragm dynamic drivers and a 20Hz-40kHz frequency response and ultralow distortion reproduction. Multiple sizes of ear tips and “wings” ensure a secure fit. Touch panels on the round outer surfaces allow access to assignable tap commands. Bluetooth 5.3 includes aptX Lossless, which delivers 16-bit 44.1kHz quality when paired with an Android device sporting Qualcomm’s Snapdragon 8+ Gen. 1 chipset or newer, but there’s still SBC and AAC so that any device can connect reliably and any listener can enjoy a customized listening session. And there’s also ANC to make sure you can concentrate more on the music.

Linsoul Kiwi Ears Quintet Quadbrid In-Ear Monitor w/ 1DD + 2BA + 1 Planar + 1 PZT Driver $175 (Was $219)

OK, so these are also not headphones. However, some call in-ear monitors IEMs, while others call them in-ear headphones. Maybe let’s split the difference at earphones. But we can all agree that brands like Kiwi Ears are using trickle-down tech in sets that offer headphone-level detailing in pocketable form. And who doesn’t want to hear more but not pay more? A quad-driver configuration used to be serious enthusiast territory but is now within entry-level reach. Packed within a snugly fitting 3D-printed resin shell, behind logo-embossed anodized metal faceplates, this five-driver-per-ear configuration offers bass that is warm without being wooly, mostly controlled while hitting perceivable subbass when called upon. The low-end buoys the lower mids slightly but not so much as to obscure texture. There’s still plenty of airy energy, with instruments isolated and impactful within the adequate soundstage. Still, the Quintet produces engaging technicalities and authentic timbre thru the upper treble. The Kiwi Ears Quintet is a crisp package, both in its look and while listening. There is appropriate depth and detail, with instruments punchy and well-positioned. You could spend more, but the Kiwi Quintet supports a balanced sound and budget with aplomb.