The Jackson entourage - consisting of his father, Reverend Jesse Jackson; his wife, Sandi Jackson; and the former congressman's two children - arrived at Maxwell Air Force Base around 4:15 a.m. Thursday.
After retrieving Jackson, their motorcade made a rear exit away from the TV cameras to begin an 800-mile, 12-hour drive through the south and up the eastern seaboard to a halfway house in Baltimore.
"I've made mistakes and I'm prayful and hopeful that we're a country of second chances, that the American people and the people of the City of Chicago will consider me for a second chance," Jackson Jr. said upon his arrival.
After the long drive, Jackson was met outside the halfway house by a cordon of news crews, mostly from Chicago. Jackson said even as he left his family, he had them in mind.
"I pray that, I pray that I can get home to them as quickly as humanly possible," Jackson Jr. said.
A few minutes later, a large duffel bag with Jackson's possessions was wheeled in, signifying that he had been told he may be here for a while, unlike some felons who merely process through and proceed directly to home confinement.
Then his wife, children, mother and other family went in to say their goodbyes until he is allowed to come home. It's not yet known how long that will be.
Jackson had to pass up seeing his seriously ill grandmother a South Carolina hospital after the Bureau of Prisons said he couldn't stop. His father, Rev. Jesse Jackson, did leave the family caravan for a visit. He also spoke to ABC7 along the way.
"His spirit is humble and remorseful yet he's going forward looking at his future," the Rev. Jackson said. "It was a tearful departure between him and some of his fellow inmates."
Jackson Jr. resigned after a 17-year congressional career, pleading guilty to using hundreds of thousands of dollars in campaign money on luxury items for himself and his family. He was sentenced to 30 months in prison.
Jackson has served about 17 months behind bars and has about six months left to serve. He does not have to serve the entire time at the halfway house. He may just spend a few days there and be released to home confinement, possibly at the family's home in Washington, D.C. The Bureau of Prisons will make that decision soon. The bureau will consider family issues and whether it is financially worthwhile to have a federal prisoner housed in a halfway house on the government's dime, when he could be at home.
In the case of former Illinois Gov. George Ryan, it was only a few hours before he was released from a halfway house to his home in Kankakee, Ill. Two complications in Jackson's case are his his drug and alcohol treatment and how being at home could affect that, and his wife Sandi, who must report to prison herself to serve a year-long sentence in the case. She is scheduled to begin serving her sentence when her husband's officially ends on Sept. 20.
"When you talk about finding a job for someone like Jesse Jackson Jr., it is obviously a different proposition than for your average inmate, so that will look a little different, but I don't expect his treatment at a halfway house to be all that radically different than anybody else's," said Gil Sofer, former federal prosecutor and ABC 7 legal analyst.
Delmarie Cobb, Jackson's former campaign manager, said while he likely won't serve in public office again, he could become a voice for public policy.
"His time has been served and he's headed to a halfway house. I mean, it gives me hope that he's well on his way to starting a new chapter in his life," Cobb said.
Sandi Jackson, a former City Council member, was sentenced to one year in prison after she was convicted of filing false tax returns.
"I know the schedule for the halfway houses is usually six months, we'll know more by tomorrow about this, but he cannot have contact with the press," the Rev. Jackson said. "All I know now is we rejoice in his return."
ABC 7 Eyewitness News will have live team coverage of Jackson's release. Watch for updates from investigative reporter Chuck Goudie and Paul Meincke.