That guitar is gorgeous! DO WANT. (hey you are in chicago too!)
I am selling some bits that might come in handy for you. I have a very nice Bartolini 5J floating pickup & endpin jack:
The Bartolini is 1/2" thick so if you have that much clearance, you should be good. The Kent Armstrong w/ ebonized cover (no pole pieces) sounds very good too but is brighter. Either one will work great.
Another option is the K&K Pure Archtop
. It is easy to install and invisible. The amplified sound is very impressive and maintains the acoustic qualities (if that is what you want). I play acoustic artchops and like bronzewound strings which you obviously can't use with a floating pickup. So the Pure Archtop was a nice solution since there is no drilling, it doesn't add weight, and i can keep the bronze strings. Here is a clip of the sound w/ the guitar direct (frist half, raw signal, no EQ):