The first person was robbed April 1 in the 2700 block of West 59th Street.
Police are searching for a person wanted in connection with a string of robberies last week in Park Manor and Chicago Lawn.
In each robbery, a man approached a person and demanded their money, Chicago police said.
The first robbery was reported April 1 in the 2700 block of West 59th Street, police said. About an hour later, another person was robbed in the 5900 block of South Washtenaw Avenue.
The man is between 20 to 25 years old and 5-foot-6 to 5-foot-11, police said.
Anyone with information is asked to call Area One detectives at 312-747-8380.