In the Chicago area, most are unfamiliar with firearms, don't really care all that much about them either way and don't research the issue at all. If a political police chief and the Tribune says they are bad, then they are bad. FWIW it's not only the Democrats in the Chicago area but the suburban Republicans who are RINOs (Republican's in Name Only) and their Republican constituents who are soccer moms and corporate middle managers etc. who have no interest in the 2nd. Similarly, downstate Democrats are pro 2nd.
In the city... well, Daley really isn't a Democrat per say. He is a dictator (with the usual bureaucratic corruption) and the Democratic machine is a tool. I was in San Fran recently and had a discussion on Daley as a true liberal. No real comparison. Take the homeless -- in SF they seem to be accommodated. In Chicago they are kept out of sight and know to keep a low profile or those friendly boys in blue will take care of them. And, just look at how his father treated the hippies in 67, and how well behaved those modern G8 summit protesters were when in town compared to Seattle

He was ready to bash heads at the drop of a hat. He also does little more than lip service to support the poor neighborhoods, etc. spending big resources in the downtown area and putting most of his police force in the upscale neighborhoods.
Still he is strongly anti 2nd. He likely has a personal opinion that "guns are bad," and as an absolute ruler his opinion becomes law. I also feel that he clearly knows there is little he can do to eliminate crime in the poor neighborhoods, could care less regardless, and gun restrictions make a good scapegoat to appear to be doing something. As noted, even the "conservative" Tribune parrots directly materials from the Brady Campaign in their editorials, and seldom features a pro 2nd opinion in actual news articles while citing any number of anti-2nd opinions, sometimes from groups you've never even heard of before. They have never done any detailed journalism on issues firearm issues using statisctics to confirm any statement made by Brady or any local politician.
It doesn't help here that the hunter and trap shooter crowd only care about their slice of the 2nd, and leave collectors and other shooters out in the cold when the quarterly magazine/assault weapon ban rolls around. The politicians use that "hunting/sporting" (not counting high power shooting as the sport it is) deal to make them feel safe that the bad du jour will keep THEIR guns safe.
Charon