Chicago is by far the best of the bunch if Insurance is what you're looking for, take it from me! Aon, CNA just to name a few..
Chicago's basically safe if you avoid the Southside and other sketchy neighborhoods, yes? Like I asked another person about the Twin Cities - what's the COL? How's the ratio of pay to rent + utilities?
I've been living on what is technically the South Side (Hyde Park) for the past six months and I've never felt unsafe in my neighborhood. Crime in Chicago is very concentrated to certain neighborhoods (Austin, Lawndale, Garfield Park, Englewood, Back of the Yards, Grand Crossing, Gresham, Roseland) and certain streets, and if you're not affiliated with a gang people generally won't hassle you. There are bad neighborhoods, but they're generally not places you'll ever have any reason to go, and there are plenty of people on the North Side who are never directly affected by those parts of the city.
Even the bad neighborhoods aren't really no-go zones. Englewood is one of the roughest parts of the city and I certainly wouldn't recommend living there, but the Whole Foods in Englewood has cheap groceries and is fine during the day. Washington Park is another place where I'd never live, but there's a nice coffee shop on 55th that I like to study at and the 55th Red Line stop (isolated in the middle of the freeway) is safe at pretty much all hours. A lot of my friends live in Woodlawn north of 63rd, and Chatham (nowhere near as violent as most but still on the South Side and majority-black, so it often gets lumped in with the others) is safe and middle-class enough to draw a Target and a number of other big-box stores.
It is worth noting that there are a few neighborhoods on the South Side that aren't crime-ridden but that have a certain hostility towards outsiders (Mt. Greenwood and particularly Canaryville). If I were moving to Chicago, I'd definitely start by looking for cheap places on the North Side, but I wouldn't rule out Hyde Park or Bridgeport (Beverly is also lovely but mostly single-family homes—probably best for owning, not renting).
As for cost of living, it's not as cheap as other Midwestern cities, but it's very reasonable by big-city standards. You
can get a one-bedroom apartment (including utilities) for $800 in Hyde Park, but if you're willing to spend $1200 you can probably get a nice studio apartment (central heat, decent internet) in a neighborhood not full of college students. Groceries aren't bad if you shop at reasonable places (Aldi or TJ's instead of Whole Foods), and if you're living close to public transit the CTA is adequate, far cheaper than a car, and entirely safe (I’m white, 19, obviously a college student, and I’ve taken the 55 through Englewood at 4am without incident). I don’t own a bike, but my friends who do say biking in the city is fine.
As for the city itself, there’s obviously plenty of stuff to do, including stuff that’s cheap/free. The city is big, but not in a way that’s overwhelming, and it’s really only as big as you choose to make it (I’ve met people who were born in Little Village who’ve never been to the Loop). More museums than you could visit, though, so you’ll never get bored. I also haven’t had any serious weather issues, though we’re going through a remarkably mild winter. The economy is fine, and as Green Line mentioned, the job market is fine (CNA, Aon, Kemper). All in all, a great place to live, and definitely much easier to live affordably in Chicago than in NYC/San Francisco.
