Police said it happened on May 28 in the Belmont Central neighborhood's 2900-block of North Mango Avenue.
The man picked a woman up and forced her into the gangway of a home, police said. He told her he would kill her if she continued to yell.
Police said the man took the victim's pants off, ripped her undergarment and tried to sexually assault her.
Surveillance video shows the suspect jumping over a fence before he ran away down the alleyway behind homes.
Police said the man fled the scene southbound down the Mango Avenue alley to George Street. He then ran eastbound to Central Avenue before heading westbound back to Parkside Avenue.
Marcelo Herrera captured blurry cell phone video of police searching with dogs outside his garage.
"As soon as I opened my back door, my garage door, I see police with the dogs everywhere," Herrera said.
Marcelo says investigators went door-to-door, looking for the attacker.
"When they told me what happened, I said 'Oh, my God.' I live over here for 15 years. Nothing happened like that," Herrera said.
Neighbor Maria Lopez says the attempted assault happened in the gangway by her home, and she woke up that morning to police knocking on her door.
"They say the lady, she was walking, and the guy, he started chase her, so they asked me if I hear something, but I say I don't hear nothing," Lopez said.
Lopez says she hopes the surveillance video released by police leads to an arrest.
"I feel scared, because I don't know if the guy is around here. I don't know if something could happen to me," Lopez said.
The man seen in that video left his gray shirt and black hoodie at the scene, police said.
The suspect is described as between 25 and 35 years old, 5-foot-7 to 5-foot-8 and weighs between 160 and 200 pounds. He has short-dark colored hair and facial hair.
Police asked anyone with information to call them at 312-746-6554.
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