A rebuttal to two common conceits about NYC vs. Chicago, in an attempt to clarify.
1. “Chicago is more segregated than New York.”
From CensusScope analysis of 2000 Census data, this is false. The usual measure of segregation is called the dissimilarity index; an index of 100 implies total segregation between two groups. The New York PMSA in 2000 had a black-white dissimilarity index of 84.3 and a Latino-white dissimilarity index of 69.3. Chicago’s comparable indices are 83.6 for black-white and 64.8 for Latino-white.
2. “You only find Midwesterners in Chicago. New York draws from all over the country.”
An admittedly dated (from 1999, using 1990 Census data) analysis by USC professor Dowell Myers [PDF, pp. 934] found that a similar proportion of New York and Chicago region residents* were born within their respective tri-state areas. 57.6% of New Yorkers were born in New York, New Jersey, or Connecticut; 60.5% of Chicagoans were born in Illinois, Indiana, or Wisconsin. For all its claims to be a national draw, only 18% of New Yorkers moved from other states/territories, while 24.8% of Chicagoans moved from outside its region (but within the country). By comparison, in the Washington, D.C. region, “long believed to be a region of transient residents who came to town for short tours as students, military officers or federal workers” (as the WaPo wrote in 1991), only 34.5% of residents were born within D.C., Maryland, or Virginia.
This particular complaint is often levied against the Lincoln Park area, with its “Big 10 frat party” feel, although fewer than 1 in 120 Chicago region residents live there. Yet the New York region’s white population is even more provincial than the Chicago region’s: fully 73.4% of New York’s white residents were born within the tri-state area, vs. 71% of the Chicago region’s.
Far more of New York’s population was born abroad (24.5% vs. 14.7%), although Los Angeles easily beats both with 30.1% of its residents being foreign-born — which, in turn, pales against Toronto’s 46%.
* Over 25.
west north 
So it’s more reasonable to say “Chicago and New York are equally segregated, at least within a few dissimilarity points.” Good for Chicago!
I haven’t heard someone say anything quite like number two, but I have heard people note that New York draws creative people in the fields of theatre, dance, music and visual art from around the country and world. Not sure what data source would have information on how to judge that.
I knew you’d chime in, and thanks. Of course, I love both cities, but was trying to put some context around things that I often hear people complaining about. I grew up attending integrated schools, and the segregation I see here is saddening indeed — but one can’t fairly single out Chicago as any worse in that regard than many other Northern cities.
Of course NYC is a bigger draw for people in the fields that it dominates, particularly in arts and media. It’s a bigger draw for immigrants, that’s for sure, including several reaches of my extended family. And yes, it attracts ambitious sorts of all stripes, since it offers more urban energy than anywhere else in Anglo America. Yet NYC isn’t some magical dimension where The Best And Brightest From Everywhere!!! frolic in their reflected glory; Chicago isn’t a second-rate backwater of lackadaisical but bitter Midwesterners. Not everyone who’s ambitious moves far from home, and not everyone who moves away is all that ambitious. The truth, of course, lies somewhere in between.
Yet I have heard a lot of complaints about Chicagoans inherently being more provincial, that its population is less dynamic and overwhelmingly Midwestern. And yes, I could understand how someone familiar with the Trixie scene might say that (although again, it’s a tiny slice of the city that’s actually mirrored in most cities worldwide). This doesn’t recognize that migration potential IS determined largely by distance, and therefore that most people in any large, old metro are going to be from those parts. A lot of people in both metros just happened to be born there, and do what they do just because that’s what people there do.
And, increasingly, that’s even the case in “newer” areas like DC: I’m always amazed to meet people who work at, say, environmental NGOs not because they care for the environment but because that’s just what people in DC do. Similarly, even I was surprised to find that a substantial plurality of Raleigh’s population growth comes from people moving from within North Carolina. I, like everyone else there, assumed that everyone moving in was a Yankee.
I’d be interested to see dissimilarity data by neighborhood. I bet my hood in Evanston is less dissimilar than most of the region.