Windy City Pro Wrestling was an American regional professional wrestling promotion based in Chicago, Illinois. Established by retired wrestler Sam DeCero in 1988, the promotion was one of several major regional territories in the Midwest during the late 1980s, along with Dick the Bruiser's World Wrestling Association, and among the oldest independent organizations in the United States until its closure in 2010.
After retiring from professional wrestling due to a back injury, Sam DeCero purchased a 95th street garage in Chicago's South Side and began training local wrestlers advertising as far as Hammond, Indiana. With Mike Gratchner, a former promoter and wrestling photographer, DeCero decided to establish his own promotion. Within a year, he had managed to secure investors including relatives, friends and co-workers and held the promotions first event at a South Side nightspot featuring Steve Regal against Paul Christy in the main event on January 30, 1988. The event, which was attended by 160 people, was successful, and soon the promotion began holding events in similar venues offering to hold cards ranging from $3,500 to $9,500.
DeCero soon began running televised wrestling events with then-22-year-old Paul Heyman, who was also working for Southeastern promotions Southern Championship Wrestling and the Continental Wrestling Federation. Their events were held at DaVinci Manor and the International Amphitheater, which later aired on WMBD-TV. During the summer, the promotion saw serious losses due to poor attendance, including losing $10,000 at a show in Rockford, Illinois and between $12,000–13,000 at the International Amphitheater. In September, despite drawing a large crowd at a card featuring Terry "Bam Bam" Gordy and Bam Bam Bigalow in the main event, the promotion still lost money
Eventually recovering after additional funding by his investors, within four years, the promotion operated two training facilities and had a weekly half-hour television show airing on SportsChannel. They also participated in several fundraisers for charity organizations including Toys for Tots, Muscular Dystrophy, Maryville City for Youth and the Chicago Coalition for the Homeless.
During the late 1980s, the promotion featured many popular wrestlers of the era including Dick Murdoch, Shigeri Akabane, Dennis Condrey, Steve Regal, and George Ringo, who acted as honorary commissioner. Prior to his death in Puerto Rico, Bruiser Brody had been scheduled to face Nord the Barbarian at the International Amphitheater in Chicago, Illinois on August 12, 1988. Other mainstays included "Mean" Mike Anthony, Trevor Blanchard Rockin' Randy, Tony Montana, and The Power Twins (Larry & David Sontag).