Kamaljit Grewal
★★★★★We had a great time in this beautiful Continental, even better when the top came off. Looking forward to renting her again.
Rent a classic car in Chicago | DRIVESHARE
Rent the best classic cars in Chicago easily with DRIVESHARE. Book and drive vintage vehicles from trusted car collectors and garages in Illinois today!
Capture the thrill of Chicago
Chicago is home to the Bulls, Bears, Cubs, Sox and Hawks, legendary hot dogs, deep-dish pizza and Italian beef (the true local delicacy) plus an iconic skyline. If you’re looking for a great driving city, look no further than Lake Shore Drive, stretching between miles of Illinois’ Lake Michigan shoreline and hundreds of soaring high-rises. Looking for a cool car to drive along the Mag Mile and State Street or a classic car to start a Route 66 road trip? Check out DriveShare’s most popular cars available for rent in Chicago, listed below.
Classic Car Rental Chicago
We all remember that first car we fell in love with, that vintage Dodge Charger in your favourite movie or the 70's Ford Mustang from your daydream cruising through Route 66. Classic car rental from Vinty gives you the opportunity to make your dreams come true and after all, dreams are better in real life!
Our rental options in Chicago give you the perfect opportunity to enjoy a classic car experience like no other. Whether you are looking for the perfect motor to take you to your wedding, or you are interested in a self-drive rental, we give you the chance to see Washington as you have never seen it before. Browse our collection of photoshoot and movie car rentals to get inspired for your next shoot or production.
We have many awesome, iconic classic cars so take a look at our collection of classic car rental Chicago and get ready to love the journey.
Cars near Chicago
1967 Ford Mustang
Chicago, IL
150 USD per day
1981 DeLorean DMC-12
Chicago, IL
1979 Mercedes-Benz 450SL
Chicago, IL
1954 Chevrolet 3600
Chicago, IL
150 USD per day
1964 Ford Galaxie
Chicago, IL
300 USD per day
1961 Ferrari 250 GT California Replica
Chicago, IL
2015 Ford Mustang
Chicago, IL
335 USD per day
1967 Chevrolet Camaro
Chicago, IL
1975 Chevrolet Cosworth Vega
Chicago, IL
1967 Volkswagen Bus
Chicago, IL
2009 Toyota Yaris
Chicago, IL
1959 Cadillac Series 62
Chicago, IL
Reviews
Viraj Suryawanshi
★★★★★Working with Paul was great! I booked this car for my sisters wedding for her now husband to arrive in. It was easy to work with Paul. He was answering emails late into the evening and also gave us options that would work best for us on arrivals and deliveries. He was diligent and informative throughout the entire process. It was very difficult finding this specific make and model in NJ/NY. Once I connected with Paul, I had full confidence that we we're going to be able to pull this off. I would recommend him to anyone!!
Curt Petersen
★★★★★I rented George’s beautiful Corvette for 9 days. PRO’s = mucho power with a six speed manual made for very thrilling moments. Exhaust notes were possibly the best part. Never once listened to the stereo. Drive up Coast Highway was a true life, bucket list testosterone day. By myself, the views between San Simion and Big Sur were outstanding AND, I had an EMPTY ROAD! No motorhomes, no trucks, no construction. CONS= CA 92 octane at $5+ a gallon (not the cars fault), and the soft top had an issue going up the last two days. Thanks George for letting me enjoy your beast!
DRIES HUYBRECHTS
★★★★★Russ really has a passion for his cars - It was easy to rent and communicate before the rental with him. When arrived the car was ready and he explained everything and let us do a quick test drive and off we went. We had amazing day and many people while on the road made a shoutout how nice the car looks! Really recommend renting from Russ.