Renting a supercar is only half the fun; the other half is where you drive it. These four routes near Chicago are favorites for an afternoon or a full day behind the wheel. Remember that rentals include a daily mileage allowance (100 miles per day on many cars in our fleet), so plan longer trips accordingly.
1. Lake Shore Drive
The classic Chicago drive. Lake Shore Drive runs along Lake Michigan with the skyline on one side and the water on the other. Early morning or later in the evening usually means lighter traffic and better light. It is the easiest scenic drive to fit into a short rental, starting right from downtown.
2. Sheridan Road and the North Shore
Head north through Evanston and follow Sheridan Road through the lakefront suburbs. Expect tree-lined curves, historic homes and glimpses of the lake. It is a relaxed, beautiful drive that suits a convertible like the BMW M8 Competition Convertible or Mercedes-AMG SL55.
3. A day trip to Lake Geneva, Wisconsin
Lake Geneva is a popular weekend escape north of the Illinois border, with a lakefront downtown and country roads on the way. It is a full-day plan rather than a quick loop, so check the mileage allowance on your car and ask about multi-day options when you request your rental.
4. Starved Rock State Park
Southwest of the city near Utica, Starved Rock is known for its canyons and bluffs along the Illinois River. The drive out takes you through open farmland, an easy cruise in a comfortable SUV such as the Mercedes-Maybach GLS 600 or Lamborghini Urus. Like Lake Geneva, plan it as a full day.
Before you go
Drivers must be 21 or older with a valid license and full-coverage insurance. Obey posted speed limits; these are scenic drives, not track days. Ready to pick a car? Browse the fleet or request a booking.
From our store
A couple of picks for your own car:
- Vantrue N2X Front & Cabin Dash Cam — 2.7K front plus cabin recording, GPS and parking mode.
- Scosche MagicMount Pro2 4-in-1 Magnetic Mount — Dash, vent or window phone mount; MagSafe compatible.
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