The first shooting occurred in the 1300-block of North Cleveland Avenue at about 10:45 p.m. Thursday night.
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Police said a man and woman were walking toward a residence when three suspects approached and at least one of them fired shots.
The man was shot and pronounced dead at Northwestern Memorial Hospital, police said. The woman was transported in serious condition to Stroger Hospital.
A few hours later, three men were shot just blocks away.
Police said the shooting occurred at about 2:23 a.m. in the 1300-block of North Hudson Avenue.
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A 41-year-old man was shot in the hip and lower back was transported to Stroger Hospital in critical condition.
Another man was shot in the leg and hospitalized in fair condition while a third man suffered a graze wound to the leg and refused medical treatment.
No one is in custody in connection with either shooting. Area Three detectives are investigating.