One of them was killed on his 15th birthday. School officials, clergy and others describe both victims as good kids.
Saturday night, Estavion Green graduated from high school. Monday night, he died in the street, steps from his home.
Green founded the peer-mediation program at the Chicago International Charter School's Ellison Campus.
The kid who classmates and teachers called "The Peacemaker" became the school's first student to lose his life to violence.
Witnesses say he was walking with female friends when someone in a car opened fire.
"We don't know why he was shot. He didn't do nothing to nobody. He don't do nothing - drink, smoke, none of that. He just wanted to go to school to make something out of his life," said Alonzo Pace, Green's cousin.
"We just never thought we would become part of the numbers," said Gia Orr, Assistant Principal at Chicago International Charter School.
School administrators say they hope to turn students' sorrow and anger into a life lesson.
"We just need them to use the tools we give them," said Orr. "Whether it's to walk away, sometimes, to make a decision not to go somewhere where everyone else is going."
A dozen miles away on a sidewalk in Humboldt Park, Jovany Diaz was talking with friends celebrating his 15th birthday when gunfire made it his last.
"I can't believe he's gone," said Jesus Diaz, Jovany's father.
Jesus Diaz says the last conversation he had with his son was about the cost of a basketball program the young sports enthusiast wanted to get into.
"I heard gunshots, and I looked out the window and the guy was chasing the dude who was shooting and then somebody said J was down," said Chanel Gonzalez, a friend of the victim.
Friends and family say Jovany was not in a gang and that gang members confronted him before the shooting started.
"It's one thing when it happens to a family member and you know he's involved in it, but he was involved in doing good, and like they say the good die young," said Caesar Rivera, Jovany's cousin.
"If you were down, he could always make you laugh," said the victim's sister Maritza Rodriguez. "He was just all about sports. He never wanted to do nothing but play video games, or play baseball or basketball."
Jovany Diaz was a freshman at Amundsen High School on the North Side and dreamed of a career in the NBA. He lived with his grandmother, and relatives say he wanted to buy her a house one day.
Now Jovany's family hopes that whoever is responsible comes forward.
"We might not get justice here, but there's always a God up there. Sooner or later you will pay," said Jesus Diaz.
A 19-year-old who was with Jovany is recovering after being shot in the hand.
Police have a vague description of the shooter and ask anyone with information to please give them a call.
Father Michael Pfleger says it's up to the community to turn killers in.
"There has to be this craziness: that we don't tell anybody - we're not going to say anything - if you don't say anything then the blood is on your hands for anybody else this person harms," said Father Michael Pfleger of St. Sabina Church.
"I'm just seeing us getting used to shooting and killing," said Pfleger.
Police say no one was in custody Tuesday night in connection with either boy's murder.
On Tuesday, Chicago Public Schools announced a summer partnership with 100 churches. They hope to provide activities, meals and other programs for as many 5,000 kids between the hours of 10 a.m. and 2 p.m. Those programs begin June 27th.