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. Head over to our Chicago Travel Guide to round out your adventure. 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


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