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I am a Chicagoan native (city proper not burbs) but I think NYC wins this battle. My reasoning is that everyone in NY regardless of race thinks its cool enough to speak it, unlike Chicago where only Whites and a select few Hispanics and even smaller numbers of Asians have our accent. I know both accents are fading in millennials and younger, but I feel like the NYC accent was more well represented in NYC that the Chicago accent was in our city.
I also think that the fact the NYC accent is associated with alpha male, take no bull types is a strong plus. It can be associated with a tough guy image unlike Chicago, where if you hear the accent it's usually in a suburb and is being used by some blue collar, non-threatening Polish-American. You don't hear the Chicago accent in the "rough" parts of Chicago. I think the opposite is true in NYC. I know not everyone who has an NYC accent is rough and tough but those that are, will sound like New Yorkers.
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