It seems while NYC is starting off their election season for Mayor as Michael Bloomberg departs after three terms, we see things heat up here in Chicago for the mayoral race in 2013. Mayor Rahm Emanuel left (or was forced out of) his gig as White House chief of staff to President Obama to run in 2011. He won overwhelmingly and has made some tough decisions since succeeding Richard M. Daley.
His base for his victory two years ago were mostly Blacks but recently they have started to waiver in their support thanks to issues of crime and the recent school closings. While the Mayor is only now beginning some damage control there is already speculation as to whom might run against him two years from now.
So far a name floating around is former Alderman and current Cook County Board President Toni Preckwinkle. An interesting possibility but who knows if she's right for the job. The thing is if people aren't happy with Rahm that's fine, but who's going to run against him that these unhappy voters will consider electing as their Mayor.
Recently I saw this post by another Mayoral challenger Jay Stone. He's an interesting case if you look at his political timeline, but what you may not see on his campaign website is that he is the son of a former Chicago Alderman. Stone's father Bernie was the oldest sitting Alderman on the Chicago City Council until he was defeated in the same election that elected Emanuel as Mayor. Stone himself attempted to run for Alderman years ago and his Aldermanic father refused to endorse him!
All the same we see possibly two people who may run against Emanuel, however, one would possibly have a better chance than the other. The other being Stone who's already asking for help to circulate petitions although I'm sure that won't start in earnest until closer to 2015.
BTW, I recommend you give a read to Stone's "Civil Rights and Election Reforms: The Right to Vote is Meaningless Without Political Competition" written on his campaign website. He attempts to illustrate why the Democratic machine has the hold on Chicago as it does. He may talk about the old time honored tradition of patronage and then brings it to today where old fashioned patronage is really illegal however from the time of the last of the big city bosses Richard J. to his son Richard M. they still know how to get the votes.