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I visited Chicago last year, and I currently work & live right outside of DC.
-Culture: Chicago
-Public School Systems (for those with children): DC
-Economy: DC. Better growth, & unemployment. Chicago does have a good economy and job diversity. Also, remember that the Government sector is more diverse than people give it credit for, it's not just politics and people can work in the government sector and not work in politics.
-Food: Chicago. More varied & better affordable options imo.
-Cost of living: Chicago
-Crime: Draw. Chicago's more known for crime, but when I looked at the statistics, it's either a draw of Chicago slightly edges out. Don't forget DC used to have the nickname of "murder capital". Too close to call imo
-Infrastructure/transportation: Draw
-Urbanity: Chicago, in a more traditional sense. Also has a significantly better skyline. Although the gap is closer than people think.
-Desirable suburbs: DC. I like the inner cities/suburbs of Arlington, Alexandria, Silver Spring, Bethesda, etc. over Chicago's offerings.
-Climate: DC has worst summers, but better winters. DC by a slight margin because it has more sunny days and less snow.
Overall: I prefer Chicago as a city, but DMV > Chicagoland imo. I also prefer DC's location near major cities & the coast. I rate the overall metro experience more than just the city, & I live & work in Arlington right now, so D.C. takes the vote for me. When I did this ranking it was closer than I expected.
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