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Chicago has what you're looking for, but it's not magically friendly. It takes time and energy to break into the social scene, just like pretty much anywhere else. It might even be a little harder than in east coast cities like New York.
Also, Cleveland is a very real city and a very big city on its way back, and very affordable. It won't be the nicest place or have the best job market right away, but if you buy in now, you should be handsomely rewarded in the near future.
Cleveland should definitely be on your list of cities ... It's a wonderful city with "A - M - A - Z - I - N - G * A - M - E - N - I - T - I - E -S"
Cleveland is very urban, it has all of the older and fantastic architecture that you would find in similar cities like Boston, Philly or Chicago ... We have the 2nd largest performing arts / theatre district in the U.S. ( Second only to Broadway in N.Y.C. ), one of the top 5 art museums in the U.S. ... fabulous suburbs to suit any taste or financial standing, awesome and eclectic city districts ( Shaker Square, Tremont, Little Italy, Ohio City, Cedar Fairmount, Edgewater )
Here, you can enjoy the WORLD RENOWNED Cleveland Orchestra ... and if you ever fall ill, there's simply no other city you that should be in ... this city has a plethora of prestigous hospitals that include the renowned "Cleveland Clinic" and "University Hospitals of Cleveland"
I really think you'd be pleasantly surprised with Cleveland ...
Monster.com also named it as having "the 7th best job market in the U.S."