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Lived here for 27 years now on North Side by JJ97
Lincoln Park, Lakeview and most recently Lincoln Square.
When my son graduates high school we will be selling our Chicago place and keeping our place in SW Michigan near the lake and finding a second place in warm weather someplace.
North side of Chicago is a great place to be a 20 something and even raise a family. I am not sure I would want to retire here. If anything I would think retirement to the Goldcoast or West Loop might be better just from a dining perspective.