Illinois Trips
What Inspires You?
Beaches ▪ Family ▪ Food ▪ Haunted ▪ Music ▪ National Parks ▪ Outdoor Adventures ▪ Relaxation ▪ Road Trips ▪ Scenic Drives ▪ Shopping ▪ Space ▪ Weekend Getaways
Destinations: Trips by State or Province ▪ Northeast ▪ South ▪ Midwest ▪ West ▪ Canada ▪ Mexico
Seasons: Spring ▪ Summer ▪ Fall ▪ Winter
Many roads lead to Chicago, that sophisticated city perched on the shore of Lake Michigan, and the most notable among them is the venerable Route 66, which offers plenty of interesting stops along the way. One is Springfield, home to the Abraham Lincoln Presidential Library and Museum. Illinois also offers scenic drives through forests, farmland and wetlands. Time for a road trip!
Nostalgic Route 66 Road Trip: St. Louis to Chicago
Southern Illinois Road Trip Features Hidden Gem Outdoor Adventures
Get more Illinois road trip ideas.
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!
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.
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!
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.
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.
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.
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.
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.
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.
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.
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.