Top Scenic Drives in Chicago with an Exotic Car

Chicago is a city built for driving. From its sweeping lakefront boulevards to its historic neighborhoods and nearby countryside, the Windy City and its surroundings offer some of the best scenic driving in the Midwest. And when you are behind the wheel of an exotic car, every one of these routes becomes an extraordinary experience. Here are the top scenic drives in and around Chicago that deserve to be experienced in something special.

1. Lake Shore Drive: The Iconic Lakefront Cruise

No list of Chicago drives would be complete without Lake Shore Drive. This 15.8-mile stretch along Lake Michigan is arguably the most famous urban drive in America. The route offers continuous views of the skyline, the lake, and Chicago’s beautiful parks and beaches.

Best car for this drive: The Lamborghini Huracan EVO Spyder with the top down. The open air lets you soak in the views and the sounds of the city while the V10 provides the soundtrack.

Highlights: Museum Campus, Grant Park, Oak Street Beach, Lincoln Park, Montrose Harbor. The S-curve near the Drake Hotel is particularly photogenic.

Distance: 15.8 miles one way. Allow 45 minutes to an hour with stops.

2. Sheridan Road: The North Shore Grand Tour

Sheridan Road is one of the most beautiful drives in the greater Chicago area. Starting from the north end of Lake Shore Drive, Sheridan Road winds through Evanston, Wilmette, Kenilworth, Winnetka, Glencoe, Highland Park, and Lake Forest. The route passes stunning lakefront estates, the Baha’i Temple in Wilmette, and the lush grounds of some of Chicago’s most exclusive communities.

Best car for this drive: The Bentley Continental GT is the ideal grand tourer for this refined route. Its elegant presence matches the neighborhoods perfectly, and its W12 engine makes effortless work of the winding road.

Highlights: Northwestern University campus, the Baha’i Temple, Ravinia Park, the Chicago Botanic Garden, Fort Sheridan historic district.

Distance: 30 miles one way from downtown. Allow 1.5 to 2 hours with stops.

3. Route 66: Begin at the Beginning

The Mother Road begins right here in Chicago at the corner of Adams Street and Michigan Avenue in the Loop. While you will not want to drive the entire 2,400 miles to Santa Monica, the first stretch of Route 66 heading southwest through Joliet, Pontiac, and Bloomington offers a nostalgic and scenic drive through small-town Illinois.

Best car for this drive: The Corvette C8 Stingray is the quintessential American sports car for the quintessential American road. Its mid-engine V8 rumble is the perfect soundtrack for Route 66.

Highlights: The Route 66 Begin sign on Adams Street, Joliet’s historic prison (seen in The Blues Brothers), the Route 66 Hall of Fame in Pontiac, classic diners and roadside attractions.

Distance: 100 miles to Pontiac. Allow 3 to 4 hours round trip with stops.

4. Starved Rock State Park: The Nature Escape

Located about 90 miles southwest of Chicago along the Illinois River, Starved Rock State Park features 18 canyons carved by glacial meltwater, waterfalls, and stunning bluffs overlooking the river valley. The drive to get there follows Interstate 80 and then scenic Route 178, transitioning from urban highway to rolling countryside.

Best car for this drive: The Porsche 911 Turbo S excels on this route. The highway portion lets you experience its effortless high-speed cruising, while the country roads near the park reward its precise handling and communication through the steering wheel.

Highlights: St. Louis Canyon waterfall, Lover’s Leap overlook, French Canyon, the Starved Rock Lodge. The fall foliage season from late September through October is spectacular.

Distance: 90 miles one way. Allow a full day for the drive and park exploration.

5. The Magnificent Mile and River North Loop

For a pure city driving experience, the loop through the Magnificent Mile and River North is hard to beat. Start on Michigan Avenue heading north from the Chicago River, cruise past the luxury shops and hotels, then wind through River North’s gallery district and restaurant row before circling back along Wacker Drive with its unique double-deck road and river views.

Best car for this drive: The Mercedes-AMG G63 is the ultimate city cruiser. Its imposing presence dominates Michigan Avenue, and the hand-built AMG V8 growl echoes perfectly off the canyon of buildings.

Highlights: The Wrigley Building, Tribune Tower, Water Tower Place, the Apple Store on Michigan Avenue, the Chicago Riverwalk, Marina City towers.

Distance: 5 to 8 miles depending on your route. Allow 1 to 2 hours with stops for photos and shopping.

6. Galena Country: The Weekend Getaway

Galena, Illinois, located about 160 miles northwest of Chicago near the Iowa border, is one of the most charming small towns in the Midwest. The drive follows Interstate 90 to US 20, then transitions into rolling hills, farmland, and the winding roads of the Driftless Area, a region that escaped glaciation and features unusually hilly terrain for the Midwest.

Best car for this drive: The Rolls-Royce Cullinan transforms this longer drive into a first-class experience. Its magic carpet ride quality and opulent interior make the 2.5-hour drive feel like 30 minutes.

Highlights: Galena’s Main Street with its 19th-century architecture, Ulysses S. Grant’s home, Chestnut Mountain Resort, the winding descent into the town from the east on Route 20.

Distance: 160 miles one way. Ideal as an overnight weekend trip.

7. Indiana Dunes: The Cross-Border Beach Run

Just an hour southeast of Chicago, the Indiana Dunes National Park offers 15 miles of stunning Lake Michigan shoreline with towering sand dunes, diverse ecosystems, and panoramic lake views. The drive along the Indiana Toll Road and then Route 12 transitions from urban expressway to beachside scenic road.

Best car for this drive: The Lamborghini Urus handles this route beautifully. Its SUV practicality lets you pack beach gear while its Lamborghini performance makes the highway portion exciting. Park it at the dunes overlook for photos that will dominate your social media.

Highlights: West Beach, the Dune Succession Trail, Mount Baldy, the views from the top of the tallest dunes looking back toward the Chicago skyline on clear days.

Distance: 50 to 60 miles one way. Allow a half day.

Planning Your Scenic Drive

No matter which route calls to you, renting an exotic car transforms a scenic drive from pleasant to unforgettable. Here are some tips to make the most of it:

• Time your drive: Golden hour provides the best lighting and the most dramatic scenery. Early mornings offer the lightest traffic.
• Plan fuel stops: Most exotic cars require premium fuel. Know where gas stations are along your route, especially for longer drives.
• Check the weather: Convertibles like the Huracan Spyder and Ferrari F8 Spyder are best enjoyed on clear days. For unpredictable weather, the Urus, G63, or Cullinan are ideal all-weather choices.
• Respect mileage limits: Standard rentals include 150 miles per day. For longer drives like Galena or Starved Rock, discuss mileage packages when booking.
• Capture the moment: Pull over safely for photos. These are the kind of experiences you will want to remember.

Start Your Chicago Driving Adventure

Chicago and its surroundings offer a remarkable variety of scenic drives, from urban boulevards to country highways to lakefront cruises. Pair any of these routes with an exotic car from our fleet, and you have the recipe for an experience that goes far beyond simple transportation.

Explore our full fleet to find the perfect car for your scenic drive, or contact us to plan a custom driving itinerary. We deliver anywhere in the Chicago metro area, so your adventure begins the moment you step outside.