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I really enjoy Chicago...

Public transportation is so complete that if you don't want to drive, you don't have to.
Waking up to a view of the lake is awesome.
Good clubs and bars.
Lots of interesting people.
Hot girls.
Good cultural stuff.
Lots of close universities so you can go to work and school.
Great restaurants.
You can smoke everywhere. (even in burger king)

I worry about my car if it is parked anywhere except my garage.
Rent is a grip.
Going out is expensive. You need to account for alcohol expense every month.
Import shops try to rip you off.
Winter is the worst.
Roads suck.
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