Illinois Road Trips


From the bright lights and hustle and bustle of Chicago to the farm lands and historical sites in the land of Lincoln, Illinois is a great spot to start your road trip from. Take a ride with Enterprise Rent-A-Car and start your journey today!


Illinois Road Trips


Drive From Chicago to Grand Rapids

Looking to go from Chicago to Grand Rapids? Driving may be your best option. Our neighborhood locations are open and ready to serve you with curbside pickup and modified cleaning procedures.
Read More

Drive From Chicago to South Haven

Looking to go from Chicago to South Haven? Driving may be your best option. Our neighborhood locations are open and ready to serve you with curbside pickup and modified cleaning procedures.
Read More

Drive From Chicago to St. Louis

Looking to go from Chicago to St. Louis? Driving may be your best option. Our neighborhood locations are open and ready to serve you with curbside pickup and modified cleaning procedures.
Read More

Drive From Chicago to Lake Geneva

Looking to go from Chicago to Lake Geneva? Driving may be your best option. Our neighborhood locations are open and ready to serve you with curbside pickup and modified cleaning procedures.
Read More

Drive From Chicago to Detroit

Looking to go from Chicago to Detroit? Driving may be your best option. Our neighborhood locations are open and ready to serve you with curbside pickup and modified cleaning procedures.
Read More

Drive from Chicago to New Orleans

Start in Chicago and end in New Orleans with this road trip itinerary. Enjoy stops in St. Louis, Memphis, and Jackson along the way to maximize the drive.
Read More

Road Trip from Chicago to Denver

Take a trip from the Windy City to the Mile High City with Enterprise Rent-A-Car. Find some unique places to stop along the way!
Read More

Drive From Chicago to Milwaukee

Looking to go from Chicago to Milwaukee? Driving may be your best option. Our neighborhood locations are open and ready to serve you with curbside pickup and modified cleaning procedures.
Read More

Drive From St. Louis to Chicago

Looking to go from St. Louis to Chicago? Driving may be your best option. Our neighborhood locations are open and ready to serve you with curbside pickup and modified cleaning procedures.
Read More

Drive From Chicago to Indiana Dunes

Looking to go from Chicago to Indiana Dunes? Driving may be your best option. Our neighborhood locations are open and ready to serve you with curbside pickup and modified cleaning procedures.
Read More

Illinois Road Trips

From the bright lights and hustle and bustle of Chicago to the farm lands and historical sites in the land of Lincoln, Illinois is a great spot to start your road trip from. Take a ride with Enterprise Rent-A-Car and start your journey from Florida today!
Read More

More Illinois Road Trip Inspiration


Nostalgic Route 66 Road Trip: St. Louis to Chicago

A weekend road trip through Illinois farmland leads to classic diners, drive-ins and big city splendor.
Read More

See All Road Trips

Looking for more road trip ideas? Check out our Road Trip Planner and choose your next journey!

Road Trip Ideas

Start A Reservation

Enjoy fast and easy car rental bookings from Enterprise Rent-A-Car at one of our 7,200 branches in cities, airports and neighborhoods near you.

Reserve a Rental Car