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Route 66, part one: Chicago to Oklahoma City – Catoosa OK Blue Whale 2026-05-25 08-17-59📷 G. Edward Johnson, CC BY 4.0

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.

12
National park loops

Indiana Dunes and northern Indiana’s Amish country

136 mi7 stops2 days
55
Themed road trips

Starved Rock canyons and Lincoln’s Springfield

243 mi8 stops3 days
31
RV & family trips

Lake Michigan's dune coast

399 mi5 stops3 days
31
Coast & island drives

Lake Michigan’s sunset coast: Saugatuck to Ludington

236 mi9 stops4 days
Route 66, part one: Chicago to Oklahoma City – Catoosa OK Blue Whale 2026-05-25 08-17-59© G. Edward Johnson · CC BY 4.0
66
Classic American drives

Route 66, part one: Chicago to Oklahoma City

873 mi12 stops4 days
Neon, diners and endless horizons – Route 66 by camper from Chicago to Santa Monica – U.S. Route 60 Amarillo, TX - Cadillac Ranch© Mobilus In Mobili · CC BY-SA 2.0
66
In-depth road trip guides

Neon, diners and endless horizons – Route 66 by camper from Chicago to Santa Monica

2,326 mi18 stops21 days

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.