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I lived my first 22 years on the North Side of Chicago. I plan on spending June-October there each year from now on to be with my family and my job allows me to have the flexibility.
I will tell you this, you want to avoid Chicago winters at all cost.
As far as living goes, Lincoln Park has nice areas but its infested with Depaul College dweebs and Yuppies. There is really no "safe" place to live in Chicago Proper as gangs and bums are in every part of town. I plan on getting a place somewhere near the gold coast downtown. Rush Street is full of tourists and Frat boys but the areas around there to the North, South, and East are very nice. South Loop is making a comeback and there are pockets of nice places to live in Wicker Park.
My advice would be live as close to the Lake and as close to the Mag Mile (where Michigan Ave meets North Lake Shore Drive) as you can afford.
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