Rank Northeastern and Midwestern metros from most liberal to most conservative

[Gass3268]

Obama won the Milwaukee metro in both 08 and 12. Cincinnati or Indianapolis is probably your best bet.

[Gass3268]

Obama only lost the Pittsburgh Metro by 14,091 votes, which isn't bad considering how much the suburban counties swung against him. I'd have to go with Cincinnati. 

[Gass3268]

Here are the Northeastern and Midwestern Metro Areas in the Top 100 ranked from the highest Obama % to the lowest:

Madison 68.89%
Springfield 64.17%
Philadelphia-Camden-Wilmington 63.92%
Chicago-Naperville-Elgin 63.74%
New York-Newark-Jersey City 63.64%
Providence-Warwick 61.53%
Cleveland-Elyria 61.46%
Hartford-West Hartford-East Hartford 60.69%
New Haven-Milford 60.65%
Toldeo 60.30%
Boston-Cambridge-Newton 60.11%
Detroit-Warren-Dearborn 59.38%
Youngstown-Warren-Boardman 59.35%
Syracuse 57.55%
Albany-Schenectady-Troy 56.83%
Buffalo-Cheektowaga-Niagara Falls 55.91%
Akron 55.84%
Scranton-Wilkes-Barre-Hazleton 55.80%
Bridgeport-Stamford-Norwalk 54.85%
Minneapolis-St. Paul-Bloomington 54.66%
Rochester 54.28%
Worcester 53.93%
Des Moines-West Des Moines 53.28%
Columbus 52.58%
St. Louis 52.49%
Milwaukee-Waukesha-West Allis 52.07%
Allentown-Bethlehem-Easton 50.44%
Pittsburgh 48.66%
Kansas City 47.84%
Dayton 46.17%
Indianapolis-Carmel-Anderson 45.43%
Harrisburg-Carlisle 45.17%
Omaha-Council Bluffs 45.17%
Grand Rapids-Wyoming 41.37%
Cincinnati 41.34%
Wichita 37.35%

[Gass3268]

To me one of the most surprising things about that list is that Springfield, Mass., is one of the country's 100 largest metro areas.

It's the 86th largest.