One of the victims caught in the crossfire was a 1-year-old girl.
The majority of the shootings took place on the city's South Side. Some of the shootings had multiple victims.
The most recent victims were two teens found Monday morning by some railroad tracks near a school bus company.
The family one of the victims struggled to deal with the aftermath of the gun violence.
"I knew this was going to happen. When you hang with gangs, this is what happens," said Charles Ibitoye, victim's father.
Ibitoye's 17-year-old son O.J. is one of over four dozen people victimized between Friday night and Monday morning. At least eight people were killed and more than 44 others shot across the city of Chicago.
On Sunday, Chicago police officials acknowledged the high number of shootings and blamed the majority on the work of gangs.
"I really can't predict the uptick in violence. If I could, then we would have stemmed some of it. I can't really say. It's an unfortunate weekend for the citizens of Chicago, but the police is doing their best to take care of it," said Dep. Superintendent Steven Peterson, Chicago Police Department.
The effects of the especially violent weekend are clear at Stroger Hospital's emergency room where a 19-year-old girl was transported after being shot in the back.
"It's was a young girl with her whole life ahead of her and now her life is drastically changed because of one bullet," said Dr. Kimberly Nagy, Stroger Hospital.
While neighborhoods and victims' families beg for the bloodshed to end, some community activist fear more lives will be lost as summer begins.
"I ask people to take a pledge of commitment to save the community, families getting back to the basics to save a youth," said Shina London, Parent Empowerment Making Connections.
The violence continued Monday on Chicago's Northwest Side in the 3000-block of North Kolmar where two people were shot. Police say a man was killed and a woman was wounded.
"A lot of young men and women pretty much they've been raised in a culture of violence so it's become the norm. So every now and then it's like a neighborhood is sitting in a big ol' tank of gasoline and somebody strikes a match, lights the gasoline and it kind of blows up every now and then," said Tio Hardiman, CeaseFire.