AirPods ProSource: iMore

This year, all three of Apple's in-ear headphones are discounted 20 - 30% off, something that has never happened on Black Friday. Which version should get? It's not necessarily all about which discount is better. It's also about your personal preferences, needs, and comfort.

I own all three versions and have some advice to help you decide whether you should buy AirPods with Wired Case, AirPods with Wireless Case, or AirPods Pro on Black Friday.

Should you buy AirPods with Wired Charging Case on Black Friday?

AirPods with charging caseSource: Daniel Bader / iMore

Apple's AirPods with Wired Charging case is discounted the most for Black Friday at 31% off. You can pick up a pair for just $110. Now, that's a great deal. Apple products rarely go on sale for more than 20%, so you may be tempted to just snatch these up without thinking. But, stop and think a moment before smashing that buy button.

Shop Cyber Monday deals at: Amazon | Walmart | Best Buy | Apple | Dell

First off, I personally think AirPods are very uncomfortable. There is no give in the bud. It's made from hard plastic. Apple did lots of research, testing the most optimum comfort level across thousands of different ear types. But, like fingerprints, all ear concha (the area just inside your ear where the bud sits) are different, and because these buds have no flexibility, there are going to be some people that just can't stand how they fit. For me, after about a half-hour, my ears feel bruised and hurt bad enough that I have to remove the AirPods. If you know your ears are somewhat small, or that the concha is tight, you may want to consider the AirPods Pro instead. They use a flexible ear tip instead of just the hard plastic bud.

If you're not worried about comfort, the only other thing to consider is whether you should buy the wired charging case or wireless charging case. Frankly, for the discounted price, I recommend just getting the wired case. You can always buy the Wireless Charging Case for AirPods separately sometime down the road if you decide you really need it.

Least expensive

AirPods with wired charging case

AirPods with Wired Charging Case

The base model AirPods with the basic case, but at a price that's hard to pass up. If you want AirPods and are on a budget, these are a fantastic price on Black Friday.

$110 $159 $49 Off

Should you buy AirPods with Wireless Charging Case on Black Friday?

AirPods with Wireless Charging Case and iPhone in the backgroundSource: Joseph Keller/iMore

AirPods with Wireless Charging Case is on sale for 25% off, which is also a very good deal. They normally cost $200, but you can take $50 off on Black Friday.

The AirPods with Wireless Charging Case are identical in every aspect to the AirPods with Wired Charging Case, except for the case itself. Similar to what I mentioned above, comfort is a factor. Consider whether your ears are small or if you have a particularly tight concha.

Is the wireless case worth the extra $40? A lot depends on what you already have in your house. Do you have multiple wireless charging pads? Do you have a wireless charging pad that supports multiple devices? If so, that's a good start.

Another question to ask yourself is, how often will you take these with you when you travel? If you're packing a wireless charger that supports multiple devices, it's a wonderful feeling to know you can leave your Lightning charging cable behind. You won't have to worry about accidentally losing your Lightning cable or wall plug.

Personally, I don't think it's worth the extra $40, but if the convenience of wireless charging really appeals to you, I could understand wanting to upgrade, especially because the Wireless Charging Case for AirPods costs $80 on its own.

Most convenient

Second Generation AirPods with wireless charging case

AirPods with Wireless Charging Case

Standard AirPods but with a wireless charging case. It's about $40 more than the base model AirPods, but wireless charging is definitely a convenience upgrade.

$150 $200 $50 Off

Should you buy AirPods Pro on Black Friday?

AirPods ProSource: iMore

OK, here's where things get interesting. AirPods Pro are actually discounted by 20% for Black Friday. Normally priced at $250, you can get a pair for about $50 off. When you click the button to See All Buying Options, scroll down to one of the new options. I guess you could buy a used pair, but the likelihood of it having crackling issues is very high. It's not worth the risk.

AirPods Pro are completely redesigned and feature flexible silicone ear tips instead of shoving the hard plastic bud directly into the ear. The first time I put the AirPods Pro in my ear, I couldn't believe how much more comfortable they were compared to the AirPods. Just having the flexibility to mold to my concha made a huge difference in comfort. Not everyone feels this way, however, I've heard from people that say they think the AirPods Pro are more uncomfortable than the AirPods. If a standard pair of earbuds with ear tips tends to hurt your ears, proceed with caution. These may not be the earbuds for you.

AirPods Pro are noise canceling and also have a feature called Transparency that enhances outside sound, just in case you're biking or jogging and want to stay aware of dangers on the street.

The sound quality of AirPods Pro is significantly better than that of AirPods, but still not exactly audiophile joy. The real reason to buy AirPods Pro is for its connectivity across all your Apple devices and the Spatial Audio feature, which is mind-bogglingly impressive.

For the price of AirPods, when they're not on sale, you can now grab yourself a pair of AirPods Pro, and in my opinion, it's going to be the best purchase you make this Black Friday if you meet a couple of important criteria.

Do you have more than one Apple device; iPhone, iPad, Apple Watch, Mac? AirPods handoff is a really nice feature, but if you only have an iPhone, you may as well just get a different brand. You won't really be able to take advantage of the continuity features.

Do you watch movies and TV shows on your device? Spatial Audio is one of the most impressive new technologies I've experienced. Using a variety of sensors, AirPods Pro determines where you're looking while watching movies and TV shows, especially on Apple TV. When you turn to the left or right, the AirPods Pro suddenly create directional audio so it seems like sound is coming from the screen you are looking at, even though you're wearing headphones.

If you are this type of person, it's worth it to spend the extra money on AirPods Pro. You will probably not see this discount again before next Black Friday, so don't pass up this deal if you decide to buy.

Best of the bunch

Apple Airpods Pro

AirPods Pro

Though it's the most expensive of the three, AirPods Pro are definitely the most impressive of the three. With Active Noise Canceling, comfortable ear tips, and Spatial Audio, this is the best price you'll probably see for an entire year.

$199 $249 $50 Off

Cyber Monday Deals

Check out more Cyber Monday deals:

We may earn a commission for purchases using our links. Learn more.