Ultimate Bentley Driving Guide For Chicago

Our exotic car dealership in St. Louis is mere hours away from the greater Chicagoland area, and several of our luxury auto enthusiast customers enjoy taking their Bentley cars and SUVs on day trips throughout the area. We’ve heard several stories over the past few years and we’re able to recommend some of the best places to take a Bentley for a pure Midwest driving experience. Give us a call at 636-489-3788 or fill out our online contact form if you are looking for information on a new Bentley vehicle to cruise the streets of Chicago in.


View New Bentley Inventory

City of Chicago Riverview

Best Places To Cruise in Your Bentley

  1. Chicago River area. Right in the heart of downtown, the Chicago Riverwalk is one of the best places to cruise in your Bentley. From the gorgeous architecture to the recently redone roads, Chicago’s Riverwalk is the ideal place to be seen.
  2. Lake Shore Drive. The awesome view of the lake on your right. The impressive skyline on your left. And you in your Bentley GT V8 cruising up the LSD.
  3. Galena territory. Not even close to Chicago, but we’ll include it because it’s great for driving, it’s close enough that you can get there and back in less than six hours, and it’s twisty and isolated. Perfect for cruising in the Bentley Mulsanne.

Best Places To Hear Your Bentley’s Engine

  1. Route 171 southwest of the city. Wind through Summit and Argo, but then it the road leads you into the forest preserves and you can hear the awesome sound of your Flying Spur as you open up the throttle.
  2. Route 25 along the Fox River offers riverside scenery and a great road to listen to your Bentley Continental.
  3. Starved Rock State Park near Utica, IL. Far outside of Chicago, but worth the trip. The highways are recently paved and rarely congested. Ideal for packing up your Bentayga and hearing the mighty V12.

2016 Bentley Continental GT Convertible

Best Places to Take the Top Down on Your Bentley Convertible

  1. North Sheridan Road. From Loyola University to Irving Park Road, North Sheridan offers impressive views of nature and the city, but offers a great drive in the late spring or early fall. An absolute must for any Bentley Convertible owner.
  2. Illinois Route 66. Take I-57 S to I-72 W and you’ll find your Bentley convertible on the original American highway. It’s smooth sailing with interesting towns and sights built to evoke the history of Route 66.
  3. The Morton Arboretum in Lisle, IL. About 25 miles west of Chicago, but there are nine miles of paved roads to open your convertible and enjoy the scenery. It’s beautifully maintained year-round and is just a short trip away from your condo or townhome in the city.

Where to Park Your Bentley in Chicago

Every exotic car owner wants to avoid a Ferris Bueller situation when they leave their car with a valet or at a parking garage, but there are a few tips Bentley owners should heed to avoid having their ultra-luxury model go on an unwanted joy ride.
  • Consider giving the valet special instructions...and a generous tip before parking your car.
  • Look over your car carefully when you get it back, especially on the front and rear bumpers and corners.
  • Don’t leave anything of value in your car. This goes for digital cameras, smartphones, tablets, everything. Take it with you and it won’t go missing while you’re gone.
  • Only leave the key. Hopefully, your exotic comes with a valet key that lacks the keyless entry, but never hand your full set of keys to another person.
  • Consider using apps to find the best deals on parking in the city


Do you still have questions about driving through the Chicagoland area? Our team has a few other ideas we can share or we can find the ideal Bentley sedan, convertible or SUV to take to the back roads, lonely highways, and scenic views. Get in touch with our product and brand specialists through our online contact form or by phone at 636-489-3788 to have any questions answered about our available Bentley inventory or your exotic car in your driveway.


View New Bentley Inventory


2016 Bentley Continental GT V8 S
Contact Us Today