Quick answer
Chicago rewards three very different drives. DuSable Lake Shore Drive is the postcard — the skyline on one side, Lake Michigan on the other, best with the top down and no schedule. Sheridan Road north of Evanston is the driver's route — a winding, tree-lined run through the North Shore suburbs where the rhythm of the curves matters more than speed. And Starved Rock State Park, about 90 miles southwest along the Illinois River, turns the rental into a proper day trip with open interstate, riverside two-lane, and canyon hikes at the far end. Each daily rate on our Chicago fleet includes a set mileage allowance — additional miles are billed per mile — so tell the concierge which route you're planning and the quote will cover it.
DuSable Lake Shore Drive: the skyline reel
The obvious one, and still the best introduction. Lake Shore Drive runs the length of the city's lakefront with the skyline stacked on one side and open water on the other — the view that makes every visiting exotic look like it's in a commercial. Be honest with yourself about what this drive is: speed limits are modest and enforced, traffic is real, and the payoff is scenery and presence, not pace. That's exactly why a convertible wins here — top down in the Huracán EVO Spyder or the Porsche 718 Boxster, the lakefront becomes the soundtrack's backdrop. Go early on a weekend morning for the emptiest pavement and the softest light, or after dark when the skyline switches on and a silent Porsche Taycan fits the mood.
Sheridan Road: the North Shore run
Head north through Evanston and stay on Sheridan Road as it threads the North Shore — Wilmette (past the Baháʼí House of Worship), Kenilworth, Winnetka, Glencoe, Highland Park, and on toward Lake Forest. This is the closest thing to a driver's road inside the metro: the street narrows, bends through ravines and under old trees, and serves up lake glimpses between some of the grandest houses in Illinois. Limits are low and these are residential streets, so the pleasure is in the car's balance and the road's rhythm, not the speedometer — which is why a mid-engine Porsche or the Huracán suits it so well. Our Porsche rental page covers the current listings for that badge; the Huracán-or-Aventador question has its own guide.
Starved Rock: the day trip
When you want the car for a whole day rather than an evening, point it southwest. Starved Rock State Park sits about 90 miles from the Loop along the Illinois River — interstate most of the way out, with Illinois Route 71 hugging the river near the park as the scenic payoff. At the far end, the state's second-oldest state park (established 1911) packs 18 sandstone canyons and more than 13 miles of trails into the bluffs above the river — waterfalls after rain and bluff-top overlooks that have nothing in common with the flatlands you crossed to get there. Plan honestly: the round trip from downtown approaches 200 miles, which is exactly the kind of day to flag to the concierge when you book so the mileage allowance matches the plan. It's also the route where the Lamborghini Urus makes its case — an SUV option to discuss for your passenger count and hiking gear.
Which car for which drive
- Lake Shore Drive: a convertible — the Porsche 718 Boxster or Huracán EVO Spyder — or the Taycan for a silent night run.
- Sheridan Road: the mid-engine cars. Check the exact Porsche listing and your route; the 911 GT3 RS is the sharper tool for drivers who want the full event.
- Starved Rock: the Urus for the crew and the cargo, or a grand tourer if it's a two-person day.
Practical notes, honestly
A few things that make these drives go smoothly. Mileage: every daily rate includes a set allowance with additional miles billed per mile — compare your whole route, including pickup and return, with the actual allowance, so quote the route when you book. Delivery: we bring the car to your home or hotel anywhere in the Chicago metro, so the drive starts at your door, not at a counter. Season: the convertible routes are at their best in the warm months, and summer weekend dates are the fleet's busiest — reserve early. The law: follow posted limits and current road conditions. The routes are suggestions, not a claim that DDE has inspected every stop. Check current access, parking and park notices before departure. Our pricing guide helps compare cars and deposits.
