Originally built as a gateway between the Mississippi River and the Great Lakes, Chicago has always had a deep love and connection to the Chicago River and Lake Michigan. During warm weather, its harbors and marinas are packed with a public excited to glide out into open blue waters for some aquatic adventure! Choose between a river-ready pontoon boat or lake tested sailboat then grab your nearest and dearest for some fun. See the buildings and parks iconic to the Windy City from a whole new perspective on a Chicago scenic cruise.