The shootings took place from 6 p.m. Friday until 11:59 p.m. Sunday. The latest shooting came in the Morgan Park neighborhood, where two people were killed and three wounded.
Police said a group was gathered in the 11300-block of South Carpenter at about 11:52 p.m. when someone fired shots in the direction of the group.
Police said 26-year-old man and 41-year-old man were both shot in the head and transported to the hospital, where they were pronounced dead.
RELATED: 2 young boys among 3 shot in Auburn Gresham, Chicago police say
Three others were also shot. Police said another 26-year-old man was shot in the head and transported to Advocate Christ Hospital in critical condition.
A 37-year-old man was shot in the leg and transported to Roseland Hospital in good condition and a 48-year-old man was shot and transported to university of Chicago Medical Center in critical but stable condition, police said.
No one is in custody in connection with the shooting.
The incident capped off a violent weekend across the city with more than four dozen shot.
Among those shot were two young boys, ages 10 and 11, who were wounded in the Auburn Gresham neighborhood. Police said they are expected to be OK.
At about 10:45 p.m. Sunday in Chatham, a shooting left a man dead.
About 10:45 p.m., the 21-year-old was standing outside a vehicle in the 8200 block of South Cottage Grove Avenue when he was shot in the back as another vehicle drove by, police said. The man was taken to the University of Chicago Medical Center, where he died.
Earlier, a man was killed in Little Village on the Southwest Side.
The 20-year-old was shot about 2:55 a.m. in the 3200-block of West Cermak Road, according to police. He was dropped off at Mount Sinai Hospital with gunshot wounds to his right cheek and the right side of his abdomen and pronounced dead a short time later.
About 20 minutes before that, a man was killed and a woman was injured in the Loop.
They were in a vehicle heading north in the 300-block of North Wabash Avenue about 2:35 a.m. when they saw a group of males on the east side of the bridge over the Chicago River arguing with someone in the middle of the street, according to police. The male in the street fired a handgun toward the group, but hit the man and woman in the vehicle. The victims drove to the first block of East Wacker Drive, where they flagged down police officers and asked for medical attention.
The man, 35-year-old Gregory Crafword of Maywood, was shot in the neck and taken to Northwestern Memorial Hospital, where he died, according to police and the Cook County Medical Examiner's Office. The woman, 25, was shot in both arms and taken to Northwestern in serious condition.
On Saturday morning, a man was shot to death in Humboldt Park on the West Side.
Anji Webster, 26, was shot multiple times at 6:28 a.m. in the 3400-block of West Ohio Street, police and the Cook County medical examiner's office said. He was pronounced dead at the scene.
About three hours earlier, another man was killed in Little Village.
Miguel Rios, 18, was driving south on Washtenaw Avenue at 3:28 a.m. when someone shot at him, authorities said. He was struck in the armpit and crashed the vehicle into a tree in the 2600-block of West 24th Street. Rios, who lived in Gage Park, was pronounced dead at the scene.
Less than 20 minutes before that, one man was fatally shot and four other people were injured in Lawndale on the West Side.
The group was standing on the sidewalk and street at 3:12 a.m. in the 1600-block of South Keeler Avenue when two males fired shots, officials said. Twan Thigpen, 25, was shot in the chest and taken to Mount Sinai Hospital, where he was pronounced dead.
A 36-year-old woman was shot in the left leg, a 32-year-old man was shot in the right arm, police said. Two other men, whose ages were not immediately known, were also each shot in the right leg. All four were taken to Mount Sinai Hospital in good condition.
Nearly two hours earlier, a 67-year-old man was fatally shot in Austin on the West Side.
He was walking on the sidewalk about 12:30 a.m. in the 4900-block of West Hubbard Street when someone fired shots from a vacant lot, police said. The man was shot in the neck and pronounced dead at Stroger Hospital.
The weekend's earliest homicide killed one man and injured another Friday night in Chatham on the South Side.
They were in a first floor apartment about 9:52 p.m. in the 8200 block of South Drexel Avenue when a male kicked in the door and opened fire, authorities said. Derek Teague, 60, was shot in the neck and pronounced dead at the scene. He lived in Bronzeville.
A 23-year-old man was hit in the arm and taken to the University of Chicago Medical Center in fair condition, according to police.
The weekend's first shooting wounded three people, including a 14-year-old boy, a few hours earlier in the same block.
The trio was on the sidewalk about 5:30 p.m. in the 8200 block of South Drexel when a vehicle drove up and someone inside opened fire, police said. The teen was struck in the face and taken to Comer Children's Hospital. A 21-year-old man was struck in the arm, and a woman, 27, was shot in the buttocks. They were taken to the University of Chicago Medical Center.
Chicago fire officials said the trio was transported in serious-to-critical condition but stabilized at the hospital.
A 14-year-old boy was shot Saturday night in Gresham on the South Side.
He was on the sidewalk about 9:30 p.m. in the 7600-block of South Green Street when someone approached with a handgun and fired shots, according to police. The teen was hit in the upper right side of his back and his right shoulder and taken to the University of Chicago Medical Center in good condition.
In the afternoon, two boys were shot during a dice game in Lawndale.
The teens, 14 and 17, were playing dice about 3:35 p.m. on a sidewalk in the 1500-block of South Sawyer Avenue when someone in a vehicle pulled up and opened fire, police said. The 17-year-old was shot in the groin and the 14-year-old was struck in the buttocks. Both were taken to Mount Sinai Hospital, where they were in good condition.
Another teenage boy was shot early Saturday at a gas station in Belmont Central on the Northwest Side.
The 17-year-old was pumping gas at a gas station about 2:35 a.m. in the 5500-block of West Diversey Avenue when someone fired shots from a black SUV, according to police. The boy was shot in the back and taken to Community First Medical Center. He was transferred to Stroger Hospital in fair condition.
About an hour and a half before that, another 14-year-old was wounded in Albany Park on the Northwest Side.
The boy was shot in the left hand at 12:58 a.m. in the 3600 block of West Argyle Street, police said. He refused to tell police about the circumstances of the shooting. He was dropped off at Swedish Covenant Hospital and transferred to Lurie Children's Hospital in good condition.
On Friday night, another teen was shot in Englewood on the South Side.
The 17-year-old was standing on the sidewalk about 9:47 p.m. in the 6900 block of South Lafayette Avenue when someone fired shots from a black sedan, police said. The boy was struck in the leg and arm and was taken to the University of Chicago Medical Center in fair condition.
Three more people were wounded in a single shooting about 10 minutes earlier in Roseland on the South Side.
They were hanging out on the sidewalk about 9:35 p.m. in the 10900 block of South Wentworth Avenue when someone fired shots from a red sedan, police said. Two 49-year-olds were each struck in the leg and taken to Christ Medical Center in Oak Lawn in good condition. The third man, 42, was shot in the foot and taken to Roseland Community Hospital in good condition.
Sun-Times Media Wire contributed to this report