Ryan Sheckler and Torey Pudwill head to Chicago in this episode of Sheckler Sessions. After their plans to participate in the Chicago stop of the Red Bull Flugtag were dashed by windy weather, the boys decide to investigate the local skate scene and stoke out some fellow boarders. After an initial session at a huge stairset, Ryan calls out via Twitter to meet up at a skatepark for an impromptu product giveaway contest and autograph signing for all the local riders. Lastly, not satisfied with their cancelled flight plans, Ryan takes a ride on another sort of craft to finish up this episode of Sheckler Sessions.