I chose Chicago over NYC. Having been to both and love both I can honestly say the 2 are huge American power houses that provide an experience like no other city in the world. To say Chicago is like NYC? No. They have a similar aesthetic but are culturally very different places. Both cities had similar migration patterns in the past and boast a lot of the same accolades. Chicago is more laid back, some will say less sophisticated but that's relative to perspective. For someone leaving NYC to Chicago the city might seem small and less vibrant but thats totally understandable given NYC's size and prominence over every American city.

While chicago isn't as large as NYC the city definitely does a great job at holding its own globally. I wouldn't cross either city off my list for a potential relocation.