I longboarded in Chicago over the summer and it was really cool. My friend had a skateboard and nobody else had anything but it was still fun. Since I have two boards now I hope to go back in the next little while and skate around the city. While I love my country hill bombing, you just feel really free and empowered tearing up a big city and flying past people. Say, is it illegal to board in city limits in Chicago? Word on the street is that it is, ohhh well