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For example, I would like for iTunes to play thru my iMac's speakers, but iChat's notifications thru my headphones.

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Welcome to Ask Different! I've edited this question to apply to more situations so that it isn't so narrow. It would also be good if you could update the question with a little more info, like model of your receiver. Thanks! – Nathan Greenstein Oct 3 '11 at 1:07
Although I did this using Airfoil, is there a way to do it without external apps? – Marcel M. Oct 3 '11 at 2:29
I would like to do the same thing! I have a USB digital coax output going to a DAC. I would like to send the audio from any one app, iTunes, Pandora, Chrome, etc., to the USB digital coax, and then have the rest of the sound continue to come out through the internal speakers on my MacBook Pro. Has anyone found a way to do this? I know you can do it with Airfoil + Airfoil Speakers, but it introduces a couple seconds of lag. I want something direct, like an audio switchboard, but I don't want to pay more than $30 or so. – orange80 Oct 29 '11 at 0:56

If the software you're using doesn't support specifying an an audio output, you'll have to rely on a third-party utility. Someone else already mentioned Ambrosia's WireTap products, but there is one other I'm aware of: Audio Hijack Pro by Rogue Amoeba. At $32, it beats the pants off WireTap for price.

There's also a piece of software called SoundSiphon by Static Z Software that provides the same functionality as Soundflower, plus single-application audio capture. Priced at $29.

Unfortunately, there are no free utilities for this. Not even Soundflower can capture audio from individual pieces of software. I think Rogue Amoeba's relies on the same underlying magic that allows them to hijack audio from individual pieces of software for their AirPlay utility AirFoil (which allows you to route any application's audio to any AirPlay device, as well as any device running their AirFoil Speakers app).

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I can't believe I forgot about Audio Hijack Pro. I love Rogue Amoeba! – Jason Salaz Sep 17 '14 at 3:24
It seems Jack can do this for free. – Kevin Wheeler Aug 24 '15 at 11:21

The easiest way to do this depends on the application supporting it;

Some applications have a sound output (and input) picker that allows you to choose the output device, like the official app. Application Preferences Screen

(My apologies for the poor example considering I only have one output source.)

If an application is written to support it, you can simply change the device as shown above. Otherwise you'll have to rely on premium (paid) apps, such as one of Ambrosia SW's "Wiretap" series of apps. Though those are pricy, $69 for WireTap Studio and $129 for WireTap Anywhere.

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As an aside, I feel like there could be some trivial 'helper' app that could change this setting for apps that don't otherwise let you pick it. But I certainly don't know this for certain. – Jason Salaz Oct 29 '11 at 2:21

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