The attacks happened about 30 minutes apart early Sunday morning in the 6800-block of South Washtenaw Avenue and the 7000-block of South Talman Avenue, about two blocks away.
According to a community alert issued by police, the man entered each home through a window and tried to assault the women as they slept.
In each attack, the man was scared away.
Ivory Roy is in the process of relocating to South Washtenaw Avenue in Marquette Park.
She says it's frightening to think there is a sexual predator in the neighborhood.
"It's scary at the least to think that someone would come through the window while people are sleeping," said Ivory Roy, Marquette Park resident.
" It's pretty much scary because you do not know what's going to happen to you. You don't know if he's going to kill you, or...I don't know. I'd be scared pretty much," said area resident Anna Salgado.
Authorities say the man is described as a black male in the 19-to-25 age range between 5 ft.7 inches and 6 feet tall.
Detectives are reminding residents in the Marquette Park area to lock their doors and windows and to report any suspicious activity."I'm glad to know about it so I can be much more aware, so I can be on the lookout for things like that," neighbor Curtis Durns said.
Chicago resident Flordia Landfair has lived on South Talman for more than two decades. She said it was frightening to think there was a sexual predator in the neighborhood.
"It makes you be more alert, you know. I'm trying all the time to be alert in the neighborhood because it's a changing neighborhood...People are coming in and out constantly. We're getting new faces in and out of the neighborhood. You don't really know your neighbors anymore."
The Associated Press contributed to this report.