Bucktown/Wicker Park - definitely for "artisy", I wouldn't really aw the same for old town. Even though Old Town is much nicer and they have the Old town Art Fair in the summer, but if you are looking for a comparison to "The Village" in NYC -Bucktown/Wicker Park is definitley the place.
It much safer now than what it was 5-8 years ago, not sure if you remember the MTV - whatever show -Real Life in chicago, or whateve. Well it was filmed in that area - if memory serves me right? It was almost what, 4-5 years ago when that was filmed.
There are also artisy parts of Lincoln Park, Wrigleyville/Lakeview, West Loop, Andersonville, etc... just depends excatly what they are looking for - unqiue shops? unqiue restaurants? etc.