The first happened about 11:30 p.m. in the 600-block of West Buckingham Place.
The second shooting happened about 1 a.m. in the 400-block of West Aldine Avenue.
A 30-year-old man was shot and wounded during the early morning armed robbery and was taken to Illinois Masonic Hospital in fair condition.
His shooting was one of two violent attacks that happened in the North Side neighborhood within hours of one another.
Chicago police haven't said if the overnight attacks are related to each other or to a rash of recent robberies in the area that have left the neighborhood on edge.
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In the Aldine attack, the 30-year-old man was shot in the leg and robbed of his wallet and cellphone after two armed men jumped out of a gray-colored car and attacked him.
The first attack happened two hours earlier and less than a mile away, in the 600-block of West Buckingham Place.
Just before midnight, three people, two men and a woman, told police they were walking down the street around 11:30 p.m. when a dark-colored car pulled up.
Several armed men got out of the car and attacked them.
A 28-year-old man was shot in the lower back during the robbery. His two friends, a 27-year-old man and a 27-year-old woman were roughed up.
The thieves got away with the woman's purse and the victims' cellphones.
The man who was shot was also taken to Masonic in fair condition.
Area three detectives are investigating both incidents, but so far, no arrests have been made.