The neighborhood is named for those three-digit streets on the far South Side, about 17 miles from downtown. The area is part of the Roseland neighborhood.
One night in Roseland, young gang members were on guard for a carload of rivals they expected to drive by and shoot at them.
One just turned 21. If the enemy gang succeeds, his adulthood won't last long.
"As you know, it's already getting warm out there. We've already witnessed 2 shootings on the block," said Bob Jackson of Ceasefire, a community-based stop-gang-violence organization.
Jackson and other Ceasefire staff members and volunteers try to help that gangbanger live to see 22 - and not die by a slug from one.
Jackson, a former military special forces officer, directs Ceasefire in Roseland.
"90 percent of our staff are ex-offenders of some kind or another," said Jackson. He said drugs and gang involvement are common problems.
Sometimes, the gang involvement is uncomfortably close, like in the previous week, just a few steps away from Ceasefire headquarters - near a sandwich shop, where Ceasefire volunteer Chuck Winston said a little boy was shot.
"There is still blood on the wall," said Winston.
"They want to volunteer because they want to make a difference," said Jackson. "It's nice to see that bright orange going down the street and knocking on the doors."
To get an idea, the I-Team followed the orange-clad Ceasefire teams on their normal rounds in Roseland.
With some daylight left, the teams begin going door-to-door, letting residents know that they are working to prevent violence and recruiting supporters.
By nightfall, though, Ceasefire's former gang members caravan into more dangerous zones.
The so-called "violence interrupters", who say they do not pass information on to police, venture into areas where window-breaking is commonplace and is interrupted by the sound of gunfire.
"The 'hood is kinda bad. It's bad," said a neighborhood 11-year-old. When asked how often he hears gunfire, he responded: "A lot."
A 9-year-old from the neighborhood said he hears shooting every day.
"It's getting worse, like people are fighting for areas," said Roseland teenager David Scott. "Basically, people are getting into it for no reason - little petty stuff."
Gang counselors have had their hands full this year. Since the beginning of 2010, Chicago Police statistics show that the Roseland neighborhood has had more violent crime than any other section of Chicago.
High school student Juan Daniel was buried last weekend. A shrine is now on the fence in front of his home, right where Daniel was shot and killed in a gangland-style hit just before his 17th birthday.
"When we saw it on the news Friday, when we saw he was a statistic, it hurt a bit more, you know like this has hit our family," said Crystal Greene, Daniel's cousin.
Daniel was raised by relatives who said his mother was a drug addict and his father was an imprisoned gang leader.
He was hit by a hail of three dozen shots, fired from a passing van, after a phone call lured him to street.
"I don't know what could have been done differently," said Lakeisha Catledge, another cousin of Daniel. "My focus hasn't been what-if's or the why's. We have to get through this, and we have a void in our lives forever."
The final stop of the night was an attempt to prevent further bloodshed in Roseland.
This night, we found that gangbanger with the glass of cognac - still trying to justify life centered on retaliation.
"I love my guys, but at the same time they [the enemy] came through the other day and took two, so you are talking to the wrong people," he said.
"I don't come outside around here," said Roseland resident Devon Maxwell, citing "the violence and the shooting."
Maxwell said that when he comes home from school, he goes "straight in the house."
Told about Maxwell's worries, the gangbanger said "I was raised around here, 21 years in the same crib and I'm outside - I'm alive."
"You scared, go to bed, that's how it is. You scared, stay in the house, play a game or something," he said. "What do you want us to do? We protecting what the f--- is ours."
It isn't a closed circle of despair.
Anti-gang volunteer Blaque Ferguson, a junior at Corliss High School wrote a song he wants you to hear.
His song is available in full on ABC7's website - click here to listen to it.