Big Signs. Bigger Impact

“We started with two signs across from O'Hare. The idea hasn't changed: put the message where people can't miss it."

Jim Caraher, Founder

About Us

Starting in the mid-1990s, Mr. Caraher started Windsor Outdoor as a diversification of his real estate investment business. He built his first two signs on the site of office buildings he owned across the street from O'Hare Airport in Chicago. He grew Windsor into the largest Chicago-based independent sign company in the market, with 60 sign faces, almost all on Chicago-area expressways.