So I found a good deal on a new radio out of an '09 SS on eBay that had a USB plug in it.

What is involved in installing this in my HHR? Do I need to get it reprogrammed? How much does that cost? I figured if it's too involved for me I could easily sell it...

 

I'm pretty sure reprogramming is necessary.....

 

You should be able to swap it out, but then have to take it to the dealer to have it reprogrammed Eric. At least I think that would all you would have to do.

 

I tell ya... I thought I would have to swap out the stereo, speakers, etc... but I love the stock system. I picked up a 32GB usb flash drive on woot.com for $40, it holds all my MP3s and I simply don't carry any CDs in the car anymore. LOVE IT! Sure it's no tech-guy thumper... but it's enough for me. Plus I still need to conserve space back there for the pooch. 150# mastiff!!

He's about 130# here and out with me wrenchin on a bike (whats new)
http://i99.photobucket.com/albums/l3...lsDeuce015.jpg

 

The speaker system on your 06 is different than what the 09 radio is programmed for. if you don't reprogram you risk blowing out your speakers.

 

I doubt you would blow the speakers. The premium ones are 2ohm vs the base 4ohm, so yours might not be quite as loud.
However, the premium stereo is supposed to be used with the amp that comes attached to the rear subwoofer box, it may not work without an amp. Im not sure if the outputs are signal level (low) or speaker level (high) but the service manual does say they are low level going to the amp.