Chicago or Boston?

[Drover]

Cost of living is another factor in Chicago's favor.

[pacer]

I know this reply is way late, but I'm posting this for people who happen to stumple upon this when debating Chicago vs Boston via a Google Search.

I've lived both in New England and the Midwest and now live in Chicago.

One can debate all your questions, so I'll just summarize the whole thing. If you want to live in a friendlier city, with more urban options (restaurants, art exhibits, live music, theatre), cheaper housing, roomier environment, more sensible roads, better driving conditions, and with a bigger job market, Chicago is your choice.

If you want a prettier setting with access to ocean, mountains, rivers, and like living (basically) in a giant college town, like a slightly smaller city, then Boston is your choice.

Thus, that's why I live in Chicago.

The only way to know what city is for you, is visit both for a couple of weeks, talk to the people, drive around, check out housing, etc.

[paytonc]

Originally Posted by Stockholmaren

-Crime
-Cost-of-living
-Job Market
-Recreational opportunities (outdoor, beach, mountains, boating, sports etc.)
-Schools (not a priority right now, but will be eventually)
-Diversity (we’re an interracial couple)
-Liberal mindset

Cost of living will generally be higher in Boston, especially due to much higher housing prices. Jobs will be easier to find in Boston, especially in education related fields -- not just the universities, but their affiliated presses and museums spin off plenty of jobs. MBAs are in demand in both cities; the word on the street is that it's easier to get hired in Chicago, as Boston's Yankee ways rely more on social networks.

On schools: can't really speak to the situation, but Boston has more close-in, "urban" (pre-WW2) suburbs with independent schools (Brookline, Cambridge, Newton, Somerville) to choose from than Chicago (Evanston, Oak Park).

Recreation: I really can't stick up for Chicago here, having vacationed on the Cape, in Vermont, and in the Berkshires, not to mention that both NYC and Montreal are 200-300 miles away. That same distance from Chicago gets you to Detroit and Indianapolis. Sure, Michigan, Wisconsin, and Minnesota have underrated scenic treasures, but for me, hills and lakes don't match mountains and oceans.

Diversity and liberalness: my grandmother's Congressman is Barney Frank, and unlike here, Boston isn't held back by rural rubes "downstate" (Illinois state government cannot get its act together). You'll certainly see more blue NY Times bags on driveways in Boston. On day to day personal interactions, though, I've rarely noticed any real difference in how I'm treated in either city. Chicagoans' general friendliness and New Englanders' overall taciturn-ness kind of cancel out any overt problems. Blacks and Latinos in Chicago are more segregated, though:
2000 Census Data