The 16-year military veteran got a surprise escort to his home in Round Lake Beach and another surprise when he got home.
After seeing dozens of supporters, Winling stood in front of his home joking about the grand welcome his family set up.
"We're going to talk about this later... it was really nice," he said.
The Warrior Watch Riders gave the soldier a string of beads, an honorary token of appreciation, and had him sign a banner.
After that, it was time for the next surprise.
Winling walked in his home to find every room newly decorated, a massive $50,000 renovation his wife, Jill, won from a letter-writing contest sponsored by WLS radio.
"I just wrote about his career," she said. "My dad said, 'You must be a good writer.' I said, 'No, I had something to write about.'"
Winling is a soldier who has served 14 years, was wounded in Iraq, and just finished a tour in Afghanistan.
The man who made this happen financially tried to explain why he got involved in the remodeling project.
"It's nothing, I wish I could do more," said Bruce Pinsler of Galaxie Home Remodeling.
Winling said it is a gift that is much appreciated.
"It's greatly appreciated," Winling said. " We would have never done this."
Winling is on a 30-day leave.