The latest incident Sunday comes just a day after another Catholic church was hit the Mount Greenwood neighborhood. Church and community leaders worry this is a vulnerable time of year for places of worship.
The most recent crime happened overnight, at the Immaculate Conception Five Holy Martyrs church at 44th and California, Chicago police said.
"It was shock, like, what is going on?" Father Miguel Venegas said. "What is happening?"
Father Venegas is trying to make sense of a break-in, the second at his parish in as many weeks. Instead of focusing on observing advent, he's left to consider new security measures.
"An alarm, a system, that will prevent not only to steal money, but to keep people safe," Father Venegas said.
Surveillance video from Immaculate Conception Five Holy Martyrs shows a man in a hood approaching the church overnight. Another camera shows the same man inside, appearing to look around. Eventually, he's seen leaving roughly 35 minutes later.
Father Venegas said the thief only made off with $100 to $200.
Alderman Ray Lopez of the 15th Ward worries churches may be an easy target this time of year.
"Especially as we start Advent here with the Catholic faith," Ald. Lopez said. "You know, you're gonna have a lot of people going to church, making donations, putting money into these buildings."
Friday morning, Saint Christina Catholic Church in the Mount Greenwood neighborhood was hit. Police said the suspect broke a window to get inside before stealing several items. The suspect in that break-in is in custody and charges are pending.
"We want to make sure that the police are giving it all the attention that it needs to have to ensure that this does not become a routine occurrence, not just at these churches, but throughout the entire city of Chicago for the next five weeks," Ald. Lopez said.
While the cash stolen from Immaculate Conception Five Holy Martyrs won't have a lasting financial impact, Father Venegas says it is a dark cloud hanging over a celebratory time of year.
"This is a moment of hope, a moment of joy, a moment of faith, and this sacred place, and it happens like it brings like sadness and negativity and frustration to the community," Father Venegas said.
It was not clear if the person seen on security video in the most recent crime is the same person wanted for a burglary at the same church in mid-November.
Chicago police continue to investigate the crimes.