Road trips from Chicago
6 road trips that start in or near Chicago, from 2 to 21 days, each with a stop-by-stop itinerary, distances and campsites along the way.
© Chris Light · CC BY-SA 4.0National park loops
Indiana Dunes and northern Indiana’s Amish country
© Visviva · CC0Themed road trips
Starved Rock canyons and Lincoln’s Springfield
Photo by Jeff DeWitt on UnsplashRV & family trips
Lake Michigan's dune coast
© WMrapids · CC0Coast & island drives
Lake Michigan’s sunset coast: Saugatuck to Ludington
Photo by Mick Haupt on UnsplashClassic American drives
Route 66, part one: Chicago to Oklahoma City
© David Quigley · CC BY 4.0In-depth road trip guides
Neon, diners and endless horizons – Route 66 by camper from Chicago to Santa Monica
| Route | Suggested days | Distance | Driving | Stops |
|---|---|---|---|---|
| Indiana Dunes and northern Indiana’s Amish country | 2 | 136 mi | 2 h 26 min | 7 |
| Starved Rock canyons and Lincoln’s Springfield | 3 | 243 mi | 4 h 20 min | 8 |
| Lake Michigan's dune coast | 3 | 399 mi | 7 h 07 min | 5 |
| Lake Michigan’s sunset coast: Saugatuck to Ludington | 4 | 236 mi | 4 h 13 min | 9 |
| Route 66, part one: Chicago to Oklahoma City | 4 | 873 mi | 15 h 35 min | 12 |
| Neon, diners and endless horizons – Route 66 by camper from Chicago to Santa Monica | 21 | 2,326 mi | 41 h 33 min | 18 |
FAQs
What are the best road trips from Chicago?
Popular routes starting in or near Chicago: Indiana Dunes and northern Indiana’s Amish country, Starved Rock canyons and Lincoln’s Springfield, Lake Michigan's dune coast, Lake Michigan’s sunset coast: Saugatuck to Ludington and Route 66, part one: Chicago to Oklahoma City.
Is there a short road trip from Chicago?
The shortest is Indiana Dunes and northern Indiana’s Amish country: 2 days, about 136 mi.
What is the longest road trip from Chicago?
The longest is Neon, diners and endless horizons – Route 66 by camper from Chicago to Santa Monica: 21 days, about 2,326 mi with 18 stops.