The ride came to an end Sunday, which was Flag Day.
The cyclists covered two states over four days, raising money and awareness.
It was the first of what war veterans and ride organizers say will be many rides in support of those who defend their country and freedom.
For many, Sunday's Wounded Warrior Soldier Ride marked the beginning of their celebration of life. Participants rode as a part of their mission to help those broken by war to heal.
"We can hang out with people that can relate to our situation," said Iraq war veteran Sergio Lopez.
Lopez, 27, lost both legs in 2006 during his second Army tour of duty in Iraq, and he was one of dozens of injured war veterans participating in Sunday's ride.
Fellow Wounded Warrior Danielle Green-Byrd rode as a testament to May 23, 2004, the day an enemy grenade claimed her left arm while she was a military police officer stationed in Baghdad.
"In Vietnam, America forgot about the veterans that came back, and I think projects like this just keep awareness. It empowers us," Green-Byrd said.
This weekend's inaugural ride was one of seven regional rides across the country. Midwest organizer Chad Watson, a wounded warrior himself, said he hoped to help rehabilitate the spirit of wounded vets and their families by raising awareness.
"For them to know they are going to have support, only let's them know, 'Hey, I can accomplish anything,'" said Watson.
The day's activities began with a Flag Day celebration and a flag retirement. The riders were escorted by the Axemen, a firefighters motorcycle club, and their supporters.
"Being a vet myself, I can sympathize about what they are going through," said Tom Weaver, a war veteran supporter.
"It goes back to everything we stand for. It's our freedom. We owe it to them," said Migdalia Guerra of the Axemen Motorcycle Club.
The trek, which began in Waterloo, Wisconsin on Thursday ended with a celebration of victory that war veteran supporter Chris Miller wanted her children to see.
"We want our kids to understand the meaning of the important things in life," Miller told ABC7 Chicago.
For most, the Soldier Ride ended with that celebratory picnic, but for others the ride was just the beginning. One of the organizers, Kevin Hull, says some of the Wounded War veterans headed to Arlington Park race course for a day of fun sponsored by the USO of Illinois.