He is then expected to report to the Freedom Center, a halfway house on the near West Side.
Ryan is not the only former Illinois politician to live at the Freedom Center. Its past residents include Dan Rostenkowksi, Scott Fawell, Jim Laski and Betty Loren-Maltese.
"The first thing is they'll assign him a room which is a small, little victory-our own space which you never have in prison," Ryan's former chief of staff Scott Fawell said. "People can bring you clothes and a TV, make it as homey as you can."
At the end of his prison sentence, Fawell spent about three weeks at the halfway house before returning home.
Fawell expects Ryan will do the same before he's allowed to leave for home, he said. Ryan's term technically ends on July 4th.
"It reminded me of prison," former Cicero mayor Loren-Maltese said. "There's very limited movement. You have to get written permission to go anywhere."
Any inmate completing a sentence here must go through an orientation, take classes in resume-building and finances.
Much of it is a pre-requisite to finding a job though it's still unclear as to exactly what will be required of Ryan.
He will eat, like all the other residents, in the cafeteria. If and when he leaves during the day, he must return by specified time.
Privileges are limited and come only with written permission. But he will no longer have to wear an orange jumpsuit.
"Even though you're going to the halfway house, you know that halfway house is just a short term stop before you're home," Fawell said.
Though The Salvation Army runs the 210-bed house, Ryan and the others living there must abide by Bureau of Prisons rules until their sentences are complete.
When Ryan is allowed to return to his home in Kankakee, he still must meet certain reporting requirements and in the wee hours of every morning, he'll get a phone call from a BOP worker confirming his whereabouts until his sentence is complete.