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I chose Philly based on the entire metro area. It's incredibly lush and green, but Philadelphia isn't necessarily as green in the core as some of the others.
DC gets my vote for greenest near the city center. It was designed to be that way and it's one of the city's most appealing features.
I also can't fault others who have chosen Pittsburgh or Cincy. The hills do make for a lot of greenery close in.
I chose Milwaukee because, besides the extensive Milwaukee County Park System and all the green spaces along the rivers and Lake Michigan, the City of Milwaukee and several inner suburbs have street-tree canopies/inventories and management systems that, from my experience, are unmatched in any other Midwestern or Northeastern city. In several cities on the list, even in the Midwest, sidewalks are often right next to the curb, leaving no space for the planting of street trees. In Milwaukee, even in blue-collar, pre-World-War-I neighborhoods, there is typically a grassy space with evenly-spaced trees between the sidewalk and the curb. Also, Milwaukee has an extensive boulevard system with landscaped/treed medians -- many major streets (Oklahoma Avenue, Capitol Drive, S. 60th St., Hampton Avenue) are, in fact, boulevards, even if they don't have "Boulevard" in their names.
Chicago is not very green. DC and Pittsburgh are. St. Louis and Cincinnati are.
Yeah, Chicago has lots of leafy neighborhoods with good tree cover on the residential streets. But it doesn't really have the natural spaces like DC's Rock Creek Park or Philly's Wissahickon Valley.
I'm not as familiar with the others, but I would think their topography would give them a greener feel that Chicago.
The Baltimore/DC feature the largest consistent areas of USDA Hardiness zone 7-8, making them the mildest in winter of all the cities listed here in the poll. Thus, in addition to the general abundant tree coverage typical of Eastern US cities, they also provide the best opportunities of seen evergreen lush vegetation (albeit cold hardy). So I'll go with these two.
Otherwise, both regions are utterly dead and lifeless during winter. There's probably not a single green tree in sight across the entire Midwest (other than some cold-looking boreal vegetation along the Canadian borders).
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