While I agree with most of your post and would advise the OP to choose Boston a thousand times over Chicago, New Orleans can certainly give Boston a run for it's money in the history department.

As far as seafood goes: you're kidding, right? I like a good lobster or NE clam chowder as much as the next BC alum, but overall, the Big Easy easily beats Beantown in the seafood department.

Easily. Really, no contest.