Every year since 2005, the ride has raised money for the Chicago Police Memorial Foundation.
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Vicky Mcgrath joined the ride for the first time.
"It's just beautiful. We can walk up and see the memorial for the fallen police officers that were in the line of duty," she said.
Riders left Area Four Police headquarters Sunday morning and made their way through the city, ending their ride near the lakefront at the Gold Star Families Memorial Park.
Robert Perales has taken part in the ride for 15 years.
"Terrible year for law enforcement," Perales said. "It's a shame and like I said, any little thing we can do and try to support all the officers that have fallen and current police officers."
Organizers also hope to raise thousands of dollars for school supplies for children of fallen officers.
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Maria Marmolejo's husband, Officer Eduardo Marmolejo, and his partner Officer Conrad Gary were killed by a train nearly four years ago.
"The Chicago Police Memorial Foundation is one of the very many supports and foundations that continue to support me and my kids," she said.
Marmolejo said the ride was a positive experience.
"The ride was literally in the area where my husband grew up in the Back of the Yards, so I go through where he was raised and I go through a church and the hospital where he was born and where his mom worked at. It's like a full circle," she said.
The Chicago Police Memorial Foundation has more events planned, with a golf outing Monday and a candlelight vigil next month.