Road Trips From Chicago By Car


Embarking on road trips from Chicago by car offers a myriad of exciting adventures, each destination brimming with its own unique charm. Just a few hours away, Wisconsin Dells beckons with its waterparks and breathtaking rock formations, creating a perfect family retreat. Alternatively, the scenic beauty of Lake Geneva, Wisconsin, is a mere 1.5-hour drive from Chicago, inviting travelers to indulge in boat tours and leisurely strolls through historic neighborhoods.

Door County, Wisconsin

This peninsula in Lake Michigan is known for its stunning scenery, charming towns, and delicious cherries. Start your trip in the town of Fish Creek, where you can visit the Door County Maritime Museum and hike to Cave Point County Park for amazing views of the lake. Then head north to Egg Harbor, where you can take a boat tour to Washington Island or visit the Björklunden Sculpture Garden. Finally, stop in Sturgeon Bay for some cherry pie before heading back to Chicago.

The Great Smoky Mountains National Park

This iconic park is home to stunning mountain scenery, lush forests, and a variety of hiking trails. Start your trip in Asheville, North Carolina, where you can visit the Biltmore Estate and explore the vibrant downtown scene. Then drive along the Blue Ridge Parkway, stopping to enjoy the views at overlooks like Balsam Mountain and Clingmans Dome. Finally, spend a few days hiking in the park, checking out waterfalls like Rainbow Falls and Alum Cave, and maybe even catching a glimpse of some bears.

Route 66

This classic American road trip takes you from Chicago to Los Angeles on the historic Route 66. Along the way, you’ll stop in small towns like Joliet, Illinois, Springfield, Missouri, and Santa Fe, New Mexico. You’ll also see some of the most iconic sights on the road, like the Cadillac Ranch in Amarillo, Texas, and the Petrified Forest National Park in Arizona.

The Pacific Coast Highway

This scenic drive hugs the California coast from San Francisco to Los Angeles. Start your trip in San Francisco, where you can visit the Golden Gate Bridge and Alcatraz Island. Then drive south, stopping to enjoy the beaches in Santa Cruz and Carmel-by-the-Sea. In Los Angeles, you can visit Hollywood and Disneyland, or just relax on the beach.

Pacific Coast HighwayThe Northern Lights

If you’re looking for a truly unique road trip experience, try chasing the Northern Lights in Alaska. The best time to see the lights is in the winter, when the skies are dark and clear. Start your trip in Fairbanks, where you can learn about the Aurora Borealis at the International Arctic Research Center. Then drive north to Denali National Park, where you might be lucky enough to see the lights dancing over the mountains.

No matter what your interests are, there’s a perfect road trip out there for you. So pack your bags, hit the gas, and start exploring!

Michigan’s Upper Peninsula

This remote and rugged region is a paradise for outdoor enthusiasts. Start your trip in Mackinac Island, where you can ride a bike around the island and visit Fort Mackinac. Then drive north to Pictured Rocks National Lakeshore, where you can hike to waterfalls, boat through colorful sandstone cliffs, and kayak in the clear waters of Lake Superior. Finally, make your way to Copper Harbor, where you can take a scenic boat tour of the Keweenaw Peninsula and learn about the area’s rich copper mining history.
Image of Pictured Rocks National LakeshoreOpens in a new window

The Kentucky Bourbon Trail

This road trip takes you through the heart of Kentucky’s bourbon country, where you can visit some of the world’s most famous distilleries. Start your trip in Louisville, where you can tour the Jim Beam Urban Stillhouse and visit the Frazier History Museum. Then drive south to Bardstown, where you can visit Maker’s Mark and Heaven Hill Distilleries. Finally, head east to Lexington, where you can tour Woodford Reserve Distillery and visit the Kentucky Horse Park.

The Badlands National Park

This otherworldly landscape is home to towering rock formations, colorful canyons, and a variety of fossils. Start your trip in Rapid City, South Dakota, where you can visit the Black Hills Museum of Natural History and learn about the park’s geology. Then drive east to the Badlands National Park, where you can hike along the Fossil Exhibit Trail and take in the views from the Badlands Wilderness Overlook. Finally, make your way south to Custer State Park, where you can see bison, prairie dogs, and maybe even a wild turkey.

Chicago Road Trip Adventure You’ve Dreamed Of

Family Road Trips from Chicago

The Ultimate Guide to Road Trips from Chicago

10 Awesome Road Trips from Chicago That Will Make Your Adventure Unforgettable

Road Trips from Chicago for Couples In 2024


A: Late spring (May and June) and early fall (September and October) are recommended for pleasant weather and scenic views during road trips.

Q: What are some popular road trip destinations from Chicago by car?
A: Popular road trip destinations from Chicago include Wisconsin Dells, Lake Geneva, Starved Rock State Park, Galena, Door County, and Milwaukee.

Q: How far is Mackinac Island from Chicago, and is it a feasible road trip?
A: Mackinac Island is approximately a 5-hour drive from Chicago, followed by a ferry ride. While it involves some travel, it offers a unique and picturesque destination.

Q: Are there any scenic routes for road trips near Chicago?
A: Yes, the Great River Road along the Mississippi River, and the Historic Route 66 are scenic routes offering beautiful landscapes and attractions.

Q: Are there family-friendly road trip destinations near Chicago?
A: Yes, destinations like Wisconsin Dells, Door County, and Starved Rock State Park offer family-friendly activities, outdoor adventures, and scenic landscapes.

Q: What precautions should be taken for a road trip from Chicago?
A: Check weather forecasts, road conditions, and ensure your vehicle is in good condition. Plan accommodations in advance and carry essentials like maps, snacks, and emergency supplies.

Q: How long is the drive from Chicago to St. Louis for a road trip?
A: The drive from Chicago to St. Louis takes approximately 4.5 hours, making it a feasible option for a weekend road trip.

Q: Can you recommend any historic towns near Chicago worth visiting by car?
A: Galena, Illinois, is a historic town with 19th-century charm, offering historic sites, shopping, and dining, making it a great road trip destination.

You may also like...