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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!
Location

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

Featured
2007 Bentley Continental
2007 Bentley Continental
Delivered from Chicago, IL
$225
per day
Featured
1975 Chevrolet Cosworth Vega
1975 Chevrolet Cosworth Vega
Delivered from Chicago, IL
$350
per day
Featured
1964 AMC Rambler Classic
1964 AMC Rambler Classic
Delivered from Chicago, IL
$180
per day
Featured
2016 Land Rover Range Rover
2016 Land Rover Range Rover
Delivered from Chicago, IL
$899
per day
Featured
2017 Mercedes-Benz G63 AMG
2017 Mercedes-Benz G63 AMG
Delivered from Chicago, IL
$799
per day
Featured
2015 Mercedes-Benz S63 AMG
2015 Mercedes-Benz S63 AMG
Delivered from Chicago, IL
$799
per day
Featured
1967 Volkswagen Bus
1967 Volkswagen Bus
Delivered from Chicago, IL
$900
per day
Featured
2015 Ford Mustang
2015 Ford Mustang
Delivered from Chicago, IL
$335
per day
Featured
2017 BMW 320i Automatic
2017 BMW 320i Automatic
Delivered from Chicago, IL
$140
per day
Featured
1956 Chevrolet Corvette
1956 Chevrolet Corvette
Delivered from Chicago, IL
$300
per day
Featured
2021 Cadillac Escalade
2021 Cadillac Escalade
Delivered from Chicago, IL
$450
per day
Featured
2000 Mercedes-Benz E320
2000 Mercedes-Benz E320
Delivered from Chicago, IL
$100
per day
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Reviews

Zoey Pressey
Joe was beyond amazing -- super accommodating and very communicative! (Car was beautiful as well!)
Katlynn Mathis
First, the car was absolutely perfect and in excellent condition. Getting to ride home from our wedding in my childhood dream car was a perfect way to end the night. Second, the driver was absolutely delightful! He showed up early and asked if we wanted any photos with the car. We did not plan for that so we were surprised and excited to have that opportunity! He was incredibly polite and safe. I would highly recommend Michael's Motor Cars!
Lindsay Ross
Medora Levy
I had an amazing experience with Mat! He is super kind and worked with me to get to the truck for my student film shoot. It would not have been possible without him! AND he drove an hour to deliver the truck. The car itself is beautiful. I cannot recommend him enough! truly amazing! thank you for everything Mat!!
Robyn Schnaible
This little car brings joy wherever it goes, as evidenced by all of the smiles and waves we got from onlookers as we tooled around in it. Our family had an unforgettable day driving around Camden, Rockland and Rockport and we can't say enough about the customer service and communication we received. You definitely need to know how to drive a manual and be comfortable with driving an older car with unique features, but this really added to the experience for us. The car is a nice size and we were able to install two high-back boosters in the back row so our kids could ride safely. We were also able to fit a cooler and several beach bags in the trunk. What a fun and memorable experience - we would absolutely rent from Drive Maine again!
Zailey Carter
Doug & the jewel could not have been more perfect!!! Doug is so kind, flexible and responsive! The car is stunning! Everything is original and the color is even prettier in person. We loved having the 4 seats too. Amazing experience!
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