The Department of Water Management was notified of the break in the 5900-block of North Kilpatrick Avenue around 3 a.m.
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"We had a break in a valve off of the 36-inch water main and that came up to the street. Then obviously, as you saw, flooded many of the streets," Chicago Water Department Commissioner Barrett Murphy said.
Gary Litherland, director of public affairs for the water department, said crews had a hard time shutting off the water. When they managed to turn it off around 8 a.m., crews started making repairs.
"This is a big one," said Litherland, noting it was the worst he'd seen in 10 years.
Kilpatrick was closed between North Caldwell and West Peterson avenues. Caldwell and North Knox Avenue east of Peterson were also closed.
Chicago police called Peoples Gas and ComEd to shut down service to the area. The city's Department of Streets and Sanitation salted the streets.
Cars on Kilpatrick are partially submerged and residents waded through the water to get to their front doors.
Michael Lee lives on Kilpatrick. He woke up to what he thought was the sound of rain.
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"I got about 4 feet of water in the house. Maybe 3 or 4 feet of water in the house. All the wood, all the dry wall, everything is tore up," Lee said.
Patrick Callahan's basement also flooded. His carpet was soggy and water seeped into his home.
"Frustrated and angry. Particularly when you do everything to make sure you don't get leaks," Callahan said.
Dennis Hammer, who has lived in the neighborhood for 28 years, couldn't recall ever seeing so much water on his street. He said there wasn't water in his basement until Water Management crews began opening manhole covers to allow the water to drain.
"They came around and opened up all these sewers, and you see the result," Hammer said.
The water also made its way to the basement of Rebecca Doroshuk, who lives on Knox Avenue.
"I looked outside and the whole street was flooded toward Peterson, and then it slowly started to flood toward my house," said Doroshuk.
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Then very quickly, water began gushing into her basement. She said she found plastic tubs of tools floating. At its worst, Doroshuk said she had a foot of water in her basement.
"It's the second time, so we just need to get a flood control system," she said.
Darren Kelly's basement was drenched. The 25-year resident lost treasures
"It's sickening, I'm sad, distraught. What can you do?" Kelly said.
Across the street Paula Bork's fence displayed the high watermark she experienced upon waking up.
"Around 5:30 this morning, our dog started barking and then I heard the helicopters so I turned the news on and heard there was a water main break, sprang out of bed ran to the window and saw we were completely flooded," Bork said.
Her husband just happened to decide last night to bring in his 2000 Pontiac Firebird. But luck was not on Janice Schiller's side as she watched her beloved SUV get towed away
"You have to be philosophical, no one was injured, and all the damage is complete reparable," Schiller said.
Litherland said the basement flooding was not as bad as it might have been - thanks to the large amount of leaves that had collected in catch and gutter basins.
"To some extent that's good because if all of it had gone into the sewers at once, everybody would have had flooded basements," he said.
It took several hours for the water to recede. The water department said it's hard to say what caused the main to break.
"We haven't had that much variation in temperature. Sometimes that can contribute to it. But sometimes it's just a failure of the pipe with time," Murphy said.
The water department said people should document damage and submit claims to the city. As of 11 a.m., all customers had water and power.
One of the concerns when something happens to pipes like these, is that any new piping that would be brought in---which is actually not going to be needed in this case---might cause lead levels to go up. The city said this is not a concern in the situation.
The Sun-Times Media Wire contributed to this report.