A 25-year-old man was standing outside in the 200-block of South Pulaski Road in the city's East Garfield Park neighborhood just before noon, when two unknown male suspects approached.
At least one of the suspects pulled out a gun and shot at the man, police said.
The man was shot multiple times and taken to Mt. Sinai Hospital, where he died.
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A 64-year-old woman was found unresponsive in the 300-block of South Pulaski with a gunshot wound to the chest, police said.
She was also taken to Mt. Sinai, where she died.
The suspects drove away in a black sedan, traveling south on Pulaski, police said.
Area Four detectives are investigating.
At about the same time, three people were hurt in a drive-by shooting in a Humboldt Park parking lot, police said. CPD did not say if the shooting were related.