Hey, Trent! Are you trying to keep the young lions outta your back yard???
Just kidding!
Actually, I love Boston, but I don't know the music scene there. Chicago is a great town (I do live there, so I'm prejudiced). Things ain't what they used to be (read my November ITG Journal Article for more on that), but all things considered, this is a good music town to find some work in. The central proximity thing is nice, too. Milwaukee and northern Indiana are well within reach. Heck, I did a hit and run in St Louis last weekend! The bread was too good to blow off for the drive time.
If you come to Chicago, look me up! I'd be pleased to help you find your way around the gig scene.
Nick