Large flames and heavy smoke were visible coming from a four-story apartment building as early as 4:30 a.m. in the 5100-block of South Kenwood Avenue.
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Chicago police said the woman, who is in her 80s and lived on the second floor, was taken to University of Chicago Medical Center in critical condition from the incident, which began about 3:30 a.m.
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Both those in the building ablaze and those in surrounding buildings were asked to leave their homes early Tuesday.
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"Something woke me up, and I heard the fire engines coming, people were knocking on doors, saying 'fire, fire, gotta get out.' Someone on the street was screaming, 'get out of the building, the building's on fire,'" neighbor Ryan Winters said.
Chicago fire officials said there were about 250 firefighters on the scene at one point. They were fighting the fire from all angles, and, just when it seemed contained, flames began to shoot out again.
WATCH: Hyde Park apartment building fire burns out of control
Hyde Park apartment building fire burns out of control
"I woke up about 4 o'clock to noise in the backyard, and I looked out to see someone chopping down the wooden fence between the properties," neighbor Joan Allison said. "When (we) came out, we saw the panorama of fire trucks and all that and realized the building was on fire. It's very scary."
There were some street closures in the area, as crews worked to put out the stubborn fire, which had intensified by about 6:30 a.m. with flames and heavy smoke coming from the building's roof and windows.
Chicago Fire Commissioner Annette Nance-Holt said hoarding conditions on the second floor made it difficult for firefighters to access the fire early on.
The back porches were also fully engulfed in flames on the second, third and fourth floors.
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Fire crews were in defensive mode after the building's roof caved in, Nance-Holt said during a news conference about 7 a.m.
CFD commissioner gives update as fire crews battle massive Hyde Park blaze
"We're pouring tons of water on this fire," she said. "(Crews have) a lot of work ahead of them."
Nearly a dozen people were displaced by the fire.
WATCH: Hyde Park apartment building roof collapses amid heavy flames
Hyde Park apartment building roof collapses amid heavy flames
The building appears to be a total loss, but fire investigators and building inspectors will soon move in and evaluate conditions.
The cause of the fire is under investigation.