Top Roads to Drive in Chicago and Its Surroundings

Chicago is a vibrant city surrounded by a network of scenic and enjoyable roads perfect for a fun drive. Whether you're a local looking for a day trip or a visitor seeking a memorable driving experience, these routes offer stunning views, interesting stops, and a variety of landscapes to enjoy.

1. Lake Shore Drive (US-41)

As one of the most iconic driving experiences near Chicago, Lake Shore Drive runs along the eastern edge of the city, offering breathtaking views of Lake Michigan and the Chicago skyline. This route is particularly enchanting during the golden hour when the sun sets, casting a warm glow over the water and the city.

Highlights:

Enjoy the sleek modernity of the Chicago skyline as you drive by buildings like the Willis Tower (formerly Sears Tower). Take in the beautiful beaches and parks along the shoreline, such as Northerly Island and Navy Pier. Visit the Museum Campus to see attractions like the Art Institute, Shedd Aquarium, and Adler Planetarium.

2. North Shore Drive

This route takes you along the northern suburbs, where you can experience a mix of lakeside views and charming small towns. As you drive, you can enjoy the beauty of the lake and the architecture of the older buildings in towns like Evanston, Wilmette, and Highland Park.

Highlights:

Visit the beautiful parks and beaches in Evanston and Wilmette. Experience the small-town feel of Highland Park, with its historic architecture and unique boutiques. Explore the local art scene and visit galleries in places like Evanston.

3. Historic Route 66

While Route 66 no longer runs through Chicago, the stretch of the road leading out of the city remains a nostalgic and enjoyable driving experience. You'll encounter quirky roadside attractions, vintage diners, and historic buildings, making this route a must-visit for fans of Americana and classic America.

Highlights:

Experience classic roadside eats like hot dogs and funnel cakes. Visit vintage motels and restored motor courts from the golden age of road trips. Learn about the history of Route 66 through various historic landmarks and museums along the way.

4. Starved Rock State Park

About 90 minutes southwest of Chicago, the roads leading to Starved Rock offer scenic views and winding paths through wooded areas. This state park is a breathtaking destination for outdoor enthusiasts, with beautiful canyons, waterfalls, and hiking trails.

Highlights:

Marvel at the Grand Canyon of the Northeastern Illinois Region. Explore the mysterious boulder at Starved Rock, which inspired the park’s name. Go on a hike or a bike ride to enjoy the stunning natural beauty.

5. Kettle Moraine Scenic Drive

Located about two hours north in Wisconsin, this drive features rolling hills, forests, and glacial lakes. It's perfect for those who enjoy outdoor activities like hiking and biking, and it offers a tranquil and peaceful driving experience.

Highlights:

Explore the unique glacial features and rolling hills. Enjoy scenic lakes and forests, ideal for outdoor enthusiasts. Take a break at one of the popular campsites or picnic areas.

6. The Great River Road

Following the Mississippi River, this scenic byway offers beautiful views and charming small towns. You can explore historic sites, enjoy the river views, and engage in various outdoor activities, making it an ideal route for both history lovers and nature enthusiasts.

Highlights:

Visit historic sites such as Cahokia Mounds State Historic Site. Enjoy the river views and the quaint towns along the route. Engage in outdoor activities like fishing, boating, and wildlife viewing.

7. Route 12 (Rand Road)

This route winds through the northwest suburbs and offers a mix of rural landscapes and suburban charm. You can enjoy the natural beauty of parks, lakes, and forests, as well as the comfortable amenities of suburban areas.

Highlights:

Explore the numerous parks and recreational areas in the northwest suburbs. Enjoy the peaceful lakeside views and nature trails. Visit local diners and restaurants for a taste of local cuisine.

Tips for Enjoying Your Drive

To make the most of your drive, here are some tips:

Timing

Early mornings or late afternoons are the best times to avoid traffic and enjoy the scenic views. These times also provide the best lighting for photography and sightseeing.

Stops

Plan stops at local attractions, parks, or diners to make the drive more enjoyable. This will give you a chance to stretch your legs, grab a bite to eat, and take in some of the local culture.

Weather

Check the weather forecast before you go. Conditions, especially near Lake Michigan, can impact your driving experience. Rain can make roads slippery, and strong winds can make driving more challenging.

These roads offer a mix of beautiful scenery, interesting stops, and enjoyable driving experiences, making them great choices for a fun day trip from Chicago. Whether you're a local looking for a day out or a visitor seeking a memorable driving experience, these routes will provide you with a delightful journey through the beautiful landscapes of the Chicago area.