I've traveled to Chicago numerous times for client work over the years. I would simplify it down to a few items....
1) Public transit is there, but it's also ancient as shit and run down. When it's 3:00 and taking a taxi to the airport is just as fast as taking the orange line then your public transit is shit.
2) Overall job-markets are moving away from urban cities and moving more towards suburbs and other cities, see articles on where the hottest job markets are.
3) Yes, spotty neighborhoods - basically either live North or you run the risk of being near shitty parts.
Lastly...
4) The high taxation of Chicago alone should make anyone want to move. Most states/cities rely on 2 of the 3 types of taxes - Income taxes, Property taxes, and Sales taxes. Chicago (and IL in general, really) is one of the biggest cases where it relies on ALL 3 - and all 3 are substantially high.
1) wow--so driving to the airport is faster than a train in some place? You know that's in most places, right? It's not unusual
at all. For someone who claims to travel a lot to many places, you don't have much daily experience with PT to appreciate this general reality. Maybe you're thinking about places where traffic is so universally bad, that trains are more commonly quicker. If anything, you're making an argument for traffic in Chicago being pretty good. ....the big problem with the El, though, is that it's great if you want to get somewhere along the lake, but for the rest of the city, it's very bus dependent. Orange line, you're talking about Midway. I used to work at UofC and lived up North in Lakeview. It was about 1.5 hour commute either way: El + bus. If I drove along LSD, which was pretty decent at those times because I was going against commute traffic, it sometimes took only 20 or 30 minutes. ...and this is compared to the Red line, which is much faster than the other lines because about 1/3rd of it is underground. That trip I took is analogous to your downtown to Midway comparison trip (Same situation here in DC: driving to work can now take between 30-80 minutes, depending on route and traffic; taking the train+walk is about 1.5 hours, again.)
2) Some jobs are moving to suburbs, but people still like to live in the city, or they just move to the suburb and still like to work and commute to the city. People don't really make this work well for themselves. Just look at SF--pretty much all the people that can afford to live there, don't work in SF. They commute an hour+ away to those stripmall suburbs that they don't want to live in, because they want the fancy life. The same has been true in Chicago and most other big Metro areas for a very long time. All that really seems to change is that the area just gets bigger and sprawlier, and traffic gets worse because no one wants to make proper decisions about work-life balance.
^Yeah, I know I am living the same life right now that I bitch about up here, but this current job is new and I went from a ~30 minute walk to work, which I planned and chose about 4 years ago, to an unplanned transition to this new job, which I couldn't really turn down; but also no rational way to move closer to new work because the costs over there are....lol. :\