Short answer is yes.
CTA is more reliable than NYC subway, though not as comprehensive. Metra is cheaper and more reliable than metro-north or LIRR.
Amtrak to regional cities works well. South shore line and metra electric also cool. Metra plus Uber gets you anywhere in Chicagoland.
Decent number of bike lanes. Not enough but more every year. Lakeshore path is great for north-south.
Divvy bike is ok, and cheaper than citibike.
Drivers are mixed, depending on road/hood.
Rent is cheaper than coasts of course. If you knew where you were gonna work setting up a bike commute would be easy
Oh and it's a entirely flat. So so easy to bike and just go and go
t. born in Chicago, live in NYC now