Chicago residents searching for a Uber ride on its app can win free rides in February along with a chance to win "bags of swag from one of Florida’s most popular coastal counties and, in some cases, virtual tours of this area. The Chicago campaign is Uber’s first partnership with a destination marketing organization such as Visit St. Pete Clearwater. Visit St. Pete is spending about $350,000 on the Chicago campaign, putting the estimated total for the entire campaign at about $2 million.