Sweat and Sightsee Simultaneously! City Running Tours Chicago specializes in personalized and group-guided running tours through the Windy City. Part picturesque lakefront, part bustling city center, Chicago is a midwestern city with a modern flair that has something for everyone. Only a local and runner can give you an up close and personal view of the street life that makes the city so great! Our customized runs allow you to choose how far you would like to run and what areas & sights you would like to see, while our social group runs are about 5 miles long with designated stops along the way. Contact us today to get started planning your run!