While it was already mentioned, but I believe Chicago does well in news. WGN-TV (CW) has a lot of veteran news anchors & reporters that they do well in the ratings. It also helps that they have the Chicago Tribune to help them with the news, or I don't believe they'd be doing news today. WLS-TV (ABC) is #1 in their news. They also have some veteran news anchors & reporters. WMAQ-TV (NBC) to me isn't as great, since they don't report the news like they used to. WBBM-TV (CBS) has also done poorly in the ratings, & their news department also doesn't do a good job reporting it for the most part. For the blizzard, they have at least done a good job keeping their viewers informed on the conditions. WFLD (Fox) is dead last in the ratings, & not sure why they even have a news department. I have never liked their news, & almost never watch it. I only do so if WGN-TV has sports on at 9pm, & Fox is the only station with news at 9pm. While PBS station WYIN doesn't have that great of a news program, they get their stories from the NW Indiana Times, & report them on their low budget news program, aimed at NW Indiana. The Chicago stations mainly focus on Chicago & the nearby suburbs.
Now if you factor in the 2 Spanish stations, WGBO-DT (Univision) & WSNS (Telemundo), WGBO-DT beats WSNS anyday in the news. The only advantage WSNS has is that their news department is combined with WMAQ (NBC), & can share resources.
I'm not aware of many reporters getting jobs with the networks. Most of the time, I usually hear of any reporter that leaves a Chicago station usually goes to another station in another market.