Protesters said Emanuel needs to experience the journey that many children would have to take through unfamiliar and sometimes gang-infested territories to their new schools if the closures are approved.
Demonstrators marched in front of City Hall chanting "Mayor Emanuel, walk the walk! Hands off our schools" before holding a news conference near City Council Chambers.
"We are going to continue to march as we will not have our children denied a quality education in our communities," said Valencia Rias-Winstead, of the Chicago Educational Facilities Task Force. "We're loud to make sure (the mayor) hears us. It's his decision about what to do."
Parents from schools throughout the city spoke about safety fears if their children have to go to school outside of their immediate neighborhoods.
"We have an ongoing gang conflict in our neighborhood. Everybody that you talk to knows about this," said Davonda Buck, the local school council chair at West Pullman Elementary School. "It's time the mayor acknowledged that too."
The protesters chanted "Mayor Emanuel's crime scene," alluding to what they contend would happen should schools close.
Retired CPS teacher Howard Emmer, 66, held police tape saying closures would be a "crime."
"Teachers know what good education is and it isn't closures," said Emmer, who worked in the district for 30 years and was a bilingual teacher at Whittier Elementary School and Inter-American Magnet School.
The protest comes two weeks before the school board is set to vote on what would be the largest-ever round of school closings in the United States.
Protesters have also cried out about issues they say schools will face due to the closures, including possible overcrowding, school quality and what they consider a flawed financial analysis by the district.
Last week, the school district acknowledged it overestimated the savings the closures would bring the district. The district now expects to save $438 million over 10 years, down from the initially reported $560 million.
Prior to the protest, organizers said parents and community members representing at least 10 of the schools that could be affected by the closures will be present at the event.
Hearing officers who vetted the 54 proposed school closings, released reports late Monday formally opposing several of the planned closures.
James Bebley, general counsel for CPS, issued responses to each case the officers took issue with saying the hearing officers exceeded their "authority by failing to apply the law and guidelines as promulgated."