I'm in my early 30s and have a decent sized condo but can't see myself living here when I'm 45 years old. Lived in Chicago since my early 20s.
City living is no longer appealing. You can only run the lakefront so many times. You can only ride the CTA and el so many times. I've been to all the bars, clubs and restaurants.
Chicago city living is for the 20-30s crowd. At some point you want your own front yard and a living space to call your own. Having neighbors (both upstairs and downstairs) makes it seem like dorm living at times. They make noise and cook foul smelling food.
Why would anyone over the age of 45 still want to live in the city of Chicago?