The annual event took place at the Target on Clark Street in the South Loop.
Former Chicago Bears Defensive Lineman Israel Idonije came up with the idea after a young boy he met during a school visit told him he "hated" police officers.
The goal is to build community and lasting relationships.
"Then they leave the event every year, they're hugging cops, the police officers their best friends they're high-fiving. They've shopped together they've laughed together. They've cried together. It's a really warm event," Idonije said.
Around 100 children enjoyed the morning of fun. All of them are students at Chicago Public Schools.
Eleven-year old Chase Weathers is fighting brain tumor. He was able to enjoy the event on Thursday.
"I get to spend time with my family and have fun with them!" Chase said.
"This is really, really special. This has been a trying time it's been difficult for us," Chase's Mother Linnie Weathers said.
This year, at least one officer from each of the city's 77 neighborhoods was present.
"A lot of times we just see the uniform and not the person. This is when the officers and the children get to know each other as people and really get to experience a memory, and we just love that," CPD Director Glenn Brooks said.
This year was Officer Roger Heath's first-time volunteering for duty.
"It's great, being able to take Chase around to buy the things that he needs and wants for Christmas is awesome," Officer Heath said.
The kids paired up with at least one Chicago police officer to shop for presents.
Each child got $100 to spend, the only condition: get something for themselves and something educational.
As the hour passed, shopping carts not only overflowed with toys, but also new fans of the Chicago police.
After checking out, Izzy played games with the kids before having a pizza party.