Ultimate Guide to Road Trips from Chicago

Road trips are one of the most popular and exciting ways to explore the beauty of the United States. Chicago is one of the busiest and most vibrant cities in the country, making it the perfect starting point for a road trip adventure. Whether you’re looking for scenic drives, historic landmarks, or outdoor adventures, road trips from Chicago have it all. In this ultimate guide, we’ll explore the best road trips from Chicago and what to see along the way.

The Great River Road Trip

The Great River Road is one of the most scenic drives in the United States, stretching 3,000 miles along the Mississippi River. Starting from Chicago, the road trips from Chicago take you through ten states, including Wisconsin, Minnesota, and Louisiana. Along the way, you’ll see stunning views of the river, charming small towns, and historic landmarks such as the Mark Twain Boyhood Home and Museum in Hannibal, Missouri.

Lake Michigan Circle Tour

Lake Michigan Circle Tour

The Lake Michigan Circle Tour is a 1,100-mile road trip that takes you around the entire perimeter of Lake Michigan. Starting road trips from Chicago, you’ll drive through four states, including Michigan, Wisconsin, and Indiana. The trip offers stunning views of the lake, as well as opportunities to visit charming towns such as Mackinac Island in Michigan and Door County in Wisconsin.

Wisconsin Cheese Tour

If you’re a cheese lover, the Wisconsin Cheese Tour is a must-do road trips from Chicago. Starting from Madison, Wisconsin, the trip takes you through some of the state’s most famous cheese-producing towns, such as Monroe and Plymouth. Along the way, you can sample some of Wisconsin’s finest cheeses, including cheddar, colby, and gouda.

Route 66

Route 66

Route 66 is one of the most iconic road trips in the United States, and it starts just outside of Chicago. The trip takes you through eight states, including Missouri, Oklahoma, and Arizona, and offers a glimpse into the country’s past. Along the way, you can stop at historic landmarks such as the Cadillac Ranch in Texas and the Wigwam Motel in Arizona.

Indiana Dunes National Park

Indiana Dunes National Park is a hidden gem just outside of Chicago, and it’s the perfect destination for a road trip. The park offers stunning views of Lake Michigan, as well as opportunities for hiking, camping, and birdwatching. Along the way, you can also visit nearby towns such as Chesterton and Valparaiso.

Michigan Wine Trail

If you’re a wine lover, the Michigan Wine Trail is a great road trip option from Chicago. Starting from Kalamazoo, Michigan, the trip takes you through some of the state’s most famous wine regions, such as Traverse City and Leelanau Peninsula. Along the way, you can sample some of Michigan’s finest wines, including Riesling, pinot noir, and Chardonnay.

Starved Rock State Park

Starved Rock State Park is a beautiful natural area just a few hours’ drive from Chicago. The park offers opportunities for hiking, fishing, and camping, as well as stunning views of the Illinois River. Along the way, you can also visit nearby towns such as Ottawa and LaSalle.

The Great Lakes Seaway Trail

The Great Lakes Seaway Trail is a 518-mile road trip that takes you along the shores of Lake Erie and Lake Ontario. Starting from Buffalo, New York, the trip takes you through Pennsylvania and into Canada, offering stunning views of the lakes and opportunities to visit charming towns such as Niagara-on-the-Lake.

Mississippi River Trail

The Mississippi River Trail is a 3,000-mile road trip that follows the course of the Mississippi River from Minnesota to Louisiana. Starting road trips from Chicago, you’ll drive through Illinois, Iowa, Missouri, and Tennessee before reaching the final destination. Along the way, you can explore historic landmarks such as the Gateway Arch in St. Louis and the Vicksburg National Military Park in Mississippi.

The Door County Coastal Tour

The Door County Coastal Tour is a scenic road trip that takes you along the shores of Lake Michigan in Wisconsin. Starting from Sturgeon Bay, the trip takes you through charming towns such as Egg Harbor and Fish Creek, offering stunning views of the lake and opportunities for outdoor activities such as kayaking and hiking.

Conclusion – Road Trips from Chicago

From scenic drives to historic landmarks, road trips from Chicago offer something for everyone. Whether you’re a cheese lover, wine enthusiast, or outdoor adventurer, there’s a road trip that will suit your interests. So pack your bags, hit the road, and explore the beauty of the United States on a road trip from Chicago.