ok but to answer the original question if it's still relevant:
Chicago pros:
car culture and having your own car
more privacy
much quieter and certainly not as crowded
true world city attitudes-good and bad
considering it extremely rude to apply "friendly" slurs to anyone
varied nightlife
suburbia!
JEWEL f'ing OSCO and other real supermarkets for normal people
parking
diverse food that's hearty and in big portions
awesome street names
driving
that dark, dank, traditional, woodsy mood only N American cities have
unique urban culture and neighborhoods
driving
good beer
Kill Hannah
lots more but no time to mention all
your travel potential is in the hundreds of miles if you feel like getting away
Chicago cons:
getting more crowded and meaner
getting more expensive
flat landscape
your travel potential is hundreds of miles of flat farmland basically
road construction
infrastructure could do with some upgrading
very aggressive nightlife
i guess for many the spread out feel gets old fast, but i love it
summers are getting rowdier
not so many more that i can think of.
HK's the same...more pros than cons and i can get to those later.
when in in HKG in miss CHG, when in CHG, i miss HKG. don't forget what they say about grass.