"It's especially very moving because two days ago, we buried one of our own," said Phil Cline of the Chicago Police Memorial Foundation.
Officer Michael Bailey was Chicago's third officer killed by gun violence in the past two months.
"Since I've been here, we've had nine officers killed in the line of duty, which is tough. But when it's compressed in a two-month period, it drains the life out of you," said police Supt. Jody Weis.
While it may be draining, Supt. Jody Weis believes the recent losses in his department will only make his officers work harder. Many officers at Sunday's event said they knew the realities of being a cop.
"Being a police officer in any major city is always dangerous, sure. It's been a bad couple months," said Chicago Police Dept. Chief Nick Rody.
Brenda Valadez lost her brother, Officer Alex Valadez, when he was killed on the South Side one year ago. The Valadez family led Sunday's ride in a vintage police car.
The Ride to Remember traveled from the West Side to the lakefront's Chicago Police Memorial at Gold Star Park, where a special ceremony was held to remember the fallen.
"It's nice to be around other families who have gone through this because they've been in our shoes, they're in our shoes, we know what it's like," Brenda Valadez said.
The event is always attended by families of fallen officers. Brenda Valadez says these kind of events helps her family cope with the loss of her brother.
The Chicago Police Memorial Foundation contributes money toward rewards. The organization is offering thousands of dollars for the arrest and conviction of the person or persons who killed Officer Michael Bailey. Supt. Weis did not provide any new information Sunday on that investigation.