The bad ‘hoods are on the west and south sides, but well away from the tourist haunts. The Loop, Gold Coast and the Magnificent Mile shopping strip on Michigan Avenue are all fine, day and night. Also safe are Lakeview and Lincoln Park districts.
If you’re heading to the University of Chicago and to the Frank Lloyd Wright home in Hyde Park, don’t stray south into neighbouring Woodlawn, or a few blocks west into Englewood.
Streets around the Howard Red Line stop and the Wilson Red Line stop are not places you want to be.
personally I stayed at the airport hotel one trip (a convention had filled all the hotels in town). There was a WalMart next door and you could just about touch the planes coming in to land at O'Hare - it was awesome!
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Phil at the safety hub. about 5 years ago