The 50th Ward is a middle-class neighborhood on the city's far North Side, and Stone is facing a tough race from four challengers.
In Chicago's 50th Ward, you'll find a rich mix of cultures.
It's a North Side ward that has seen its share of businesses struggle and constituents seeking city services during difficult economic times.
For 37 years, the alderman representing the ward has been Bernard Stone.
He says he can't control the economic hard times but he has unique wisdom running city government.
The octogenarian says he will help the next mayor steer the city out of recession.
"We're in a very difficult situation right now. If you're life was at stake and you had to have surgery would you take surgeon with 37 years experience or would you take a intern fresh out of medical school," Stone said.
There are four people trying to unseat Stone.
Debra Silverstein is a Certified Public Aaccountant.
Some will know her as the wife of State Senator and Ward Committeeman Ira Silverstein, who unseated Bernie Stone as committeeman.
Silverstein says her motivation to run, however, came from her work in the ward.
"We have Indians, Pakistanis, Jews, Muslims all working together on the street it should be promoted not left to deteriorate they are going to be my ideas my vision to turn things around," Silverstein said.
Greg Brewer tried unsuccessfully to become the 50th Ward alderman four years ago.
The architect says it is a different time now, with a new mayor and frustrated constituents.
Brewer says the ward is ready for a change.
"Before we can begin to address the changes we're going to be facing in the coming years, we need independent, honest, accountable leadership in the ward," Brewer said.
A candidate that would bring a younger perspective to city council is a 26-year-old business man and community organizer.
Ahmed Khan's family owns a popular grocery store on Devon Avenue. He has worked for county commissioners and interfaith organizations, and is a newly wed.
Khan says his diverse, modern perspective is needed in the ward and in city council.
"He's done a lot of great work throughout his years of service, howeve,r the implementation has lowered or ceased to exist," Khan said about Stone. "I think we need to invigorate that and bring that passion into this community."
The fifth candidate for the 50th Ward is Michael Charles Moses. He is an attorney who has worked in government and has his own private practice. ABC7 was unable to reach him.
On Moses' Facebook page he says: "My philosophy has always been that the residents of the ward should be involved and advise their elected officials because your voice matters."
It will come down to whether voters are truly ready for someone new. If Stone remains, he will wield influence over the council with possibly a third new alderman.