It was the 17th annual "Shop with a Cop."
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Santa wasn't the only one looking to spread a little holiday cheer. There was also a special group of helpers during the 17th annual "Izzy's Shop with a Cop Day" at the Target on Clark Street.
Former Chicago Bears player Israel Idonije is the driving force behind the effort. He got the idea a few years ago after a young boy he met during a school visit told him he hated police officers.
"They're going to laugh together, problem solve together on their budget and they are going to start building a relationship," Ijonije said.
The kids paired up with at least one Chicago police officer to shop for presents.
"These children don't always see us in happy situations and they really invest in that personal relationship," said Commander Melinda Linas, with the Chicago Police Department.
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This year, more than 70 officers from districts across the city volunteered for the duty, many for the first time, like Officer Irma Calzada.
"She's really great. She's really nice," said young shopper, Severous Winfield.
A lot of the children planned on getting gifts for their family and friends.
Each kid gets a hundred dollars to spend. The only conditions are that they make sure they get something for themselves and something educational.
That's what 10-year-old Malakyi Wilson did.
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"I got my favorite book. I always get this when I go to the library at my school," Wilson said.
Because of partnerships with neighborhood programs, more than 100 students from families currently facing some challenging circumstances participated this year.
"That's building connections and that will make the kids feel safer when they see officers," said Muriel McDonald, a CPS school counselor.
The gifts of trust and acceptance were shared too, as the day ended as it began with lots of holiday spirit and new friendships.