Rent a classic car in Chicago // Hagerty 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. 

Cars near Chicago

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