re: What major US city (like top 50) would fare best?

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Yeah I don't think people are grasping how much rain we are talking about

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Theres a whole science behind who floods and when (hydrology). Its been a few years since I took it in college, but it comes down to 1)amount of rainfall coming down vs 2)local geography and ability to drain. Part of that is city infrastructure, but part of it is what surfaces are impervious to water, and how much flow can your outflow channels, rivers, creeks, etc can hold.

My point is that given NYC and to a lesser extent Chicagos high proportion of impervious surfaces coupled with proximity to large bodies of water that wont back up due to high water, and then youll have high immediate flooding that drains relatively quickly.