Jackson posted bail for several inmates so they could spend the holidays with their families.
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"It's a blessing because would've been his first Christmas locked up ever," said Eileen Thomas Kinzer, who waited for her son Aaron just beyond the gate Wednesday.
Aaron Kinzer had been in jail since December 14.
"It's a good feeling, brings warmness to my heart," Kinzer said.
Jackson's Rainbow PUSH Coalition led dozens of inmates in prayer on Christmas morning, preaching that those in jail are like Jesus Christ at birth.
"The babe is wrapped in swaddling clothes, meaning literally the babe is wrapped in rags. Which means it does not matter what you have on, the only thing that matters is what's on the inside," Rev. Marshall Hatch said.
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Cardinal Blase Cupich also led the Christmas service, encouraging inmates to trust their faith as they struggle.
"When we feel as though we don't count in society, that's exactly, in the darkness of our lives, where Jesus comes to meet us," Cupich said.
After Jackson's service, inmates could register to vote and the reverend promised to bring computers to the jail to help them reenter society with skills.
"Got to change my life around," said Dionte Johnson, who's been in jail since December 4. "Now it's an opportunity, now I got to go out there and do it."
Dr. Willie Wilson donated $10,000 to ensure even more inmates can be freed in the coming days.