The buildings targeted for teardown are considered hubs of gang activity in the neighborhood.
About 200 abandoned buildings will fall to the wrecking ball in this new crime-fighting effort announced by the mayor several days ago.
In the Park Manor neighborhood Thursday, crews were knocking down a building which has plagued nearby residents for more than a decade.
"I've seen everything. I've seen shooting. I've seen drugs. I've seen gangs," said Annette Jones-Williams, neighborhood resident.
The long-vacant condo building sits across from Park Manor Elementary School. In 2007, an 11-year- boy who had just left the playground was shot there by alleged drug dealers while riding by on his bike. Such crimes, neighbors hope, will now go the way of the building.
"They're not going to have a place to hide anymore. They're not going to be terrorizing, hopefully, this block anymore," said Darlene Tribue, neighborhood resident.
All the buildings are either owned by private individuals, or they're in default with a bank. The city says, in most cases, it's had to go to court to get authorization for the teardown.
"From a violence reduction standpoint, community stabilization is so critical and so key," said Felicia Davis, mayor's first deputy chief of staff.
Efforts to knock down crime by knocking down buildings is not a new idea. More than 20 years ago, a similar strategy was used against the now-defunct El Rukn gang.
Professor Harold Pollack, a crime researcher at the University of Chicago Crime Lab, says the plan has merit.
"I think there's a concern that if we just tore one of these places down that it would just move the violence and the social problems around. But actually there's a lot of evidence to suggest that if you prevent violence in a particular spot, you're actually reducing violence, not just shifting it to another place," Pollack said.
But longtime Englewood resident Charles Brown, a member of the group Action Now, fears empty lots will lead to empty blocks.
"The solution is to rehabilitate these buildings," said Brown. "We can create jobs, and that's one thing that we need here. Then we can put the community back to work."
"Often these buildings are to a point where it would just not be fiscally feasible to even try to rehab them," said Michael Merchant, Chicago Department of Buildings Commissioner.
The city hopes to encourage community and private development of those newly-vacant lots. But in many cases, the owners who let the buildings go vacant to begin with remain in possession of the property.
The city says crime tends to go down in places where residents feel empowered, and they hope this plan will accomplish that.