The two incidents happened 20 minutes apart in the city's Humboldt Park community. The first was in the 1700-block of North Humboldt Boulevard. The second attempt was in the 1900-block of North Drake.
Elizabeth Oliveras walks the 1700-block of North Humboldt Boulevard all of the time to attend class at a nearby community college. She's now on guard after two attempted sexual assaults in the area by a man being described as a "bold" offender.
"I got friends. We might come together, come with somebody, don't be alone and pay attention," said Oliveras.
The first attempted sexual assault was on the 1700-block of Humboldt Boulevard. It was around 1:30 a.m. Wednesday when police say a man in his 20s approached a 29-year-old female with a knife, demanding the woman's money.
Then police say he forced her into an entryway of her building where he tried to sexually assault her. When the victim cried out for help the suspect fled.
But police say about 20 minutes later the suspect went a couple of blocks away to the 1900-block of North Drake. There, investigators say, he was waiting in another victim's kitchen. She, too, screamed for help and he ran outside.
"I live here, and I walk here every morning so it's kind of lake, that could happen to me, which is kind of terrible actually," said resident Mylani Rios.
Police released this description of the suspect: They say he's a black male, 23-28 years old, 6'1"-6'03", 170-180 pounds. He has dreadlocks, a medium complexion, and has a teardrop tattoo below his right eye.
"I got daughters, and i always tell them the same thing, and she says, 'You're overprotective,' I would lock gates, lock windows, put screws in there," said resident Manny Velazquez.
Police are reminding women to lock their doors and walk in groups.