Self Drive Holidays in Chicago & The Great Lakes Region

Road trips from Chicago open up some of the most varied scenery in the American Midwest.

You can set off by car or motorhome and loop around the Great Lakes, discovering a world of sandy beaches, forested drives, and charming lakeside towns. Michigan’s sweeping shoreline, Wisconsin’s lighthouse-dotted peninsulas and Indiana’s quiet state parks all sit within comfortable driving distance.

Chicago is also the starting point for historic Route 66, America’s iconic ‘Mother Road’. From here, the historic highway heads south-west through Illinois’ small towns and roadside diners, before stretching all the way to California.

Browse the self drive options below or ask one of FREEDOM’s USA Travel Experts to create a self drive holiday just for you.