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978 Posts
Pros:

Museums and Cultural Outlets are top notch.
Summer Festivals (Taste of Chicago, Air and Water Show)
Easy to Navigate
Plenty of restaurants catering to a wide variety of cuisines
Plenty of things to do (even when there's snow and the temps are 10 below)
Public Transportation

Cons

Infrastructure (Roads) still need work (One study said that IL was 48th)
City Stickers are $75, License Plates are $78
Suburban Transit (pace) stops running too early in certain areas
Is still considered one of the most segregated cities
 
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