The armed suspect entered the homes during the overnight hours while the victims were asleep, police said.
The incidents took place in the 2600-block of North Lincoln Avenue at about 3:50 a.m. on Oct 16; the 3000-block of North Kenmore Avenue at about 3:56 a.m. on Oct. 19; and the 2400-block of North Jansen Avenue at about 4:30 a.m. on Wednesday.
The suspect is described as a black man, 18 to 25 years old, 5'04" to 5'10" and 150 to 180 pounds. He was wearing a black baseball hat with white writing, a gray hooded sweatshirt and a green or dark colored puffy vest.
Anyone with information is asked to contact Area North Detectives at (312) 744-8263.