Classic Car Rental Chicago, Illinois, Antique and Vintage Cars With DRIVESHARE

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.

Reviews

Cody Whaley

Absolutely beautiful car. I rented it for my sisters wedding and it made the send off magical. Henry the owner/driver was very accommodating and made sure everything was perfect. I Would highly recommend you rent this car!

Austin Kretschmar

Duke drove the getaway car for our wedding and was awesome! He showed up early to the event and was very professional the whole time. The booking process was easy and we could tell Duke planned out the route beforehand. His car also was the perfect accent for our wedding photos.

Travis Mann

Absolutely incredible car! It turns heads and everyone wants to talk to us about it. We loved it so much this is the second time we've rented from Leann. Leann is very engaging and a great person to rent from. We'll rent again next year !!

Robert Oliver

The weather didn't cooperate for the commencement cruise, but we had a nice drive out the peninsula when the sun came out. Steve and this E320 were both as nice as can be.

Erin Shaw

I surprised my husband Ryan with Ginger on our wedding day and we couldn't have had a better experience! Daniel was so flexible with all of our wedding plan changes due to the covid outbreak. He picked us up from our backyard ceremony and we went for a ride up Old Mission Peninsula and to the old hospital grounds so our photographer could take pictures and Ginger was the perfect background/feature :) Our families loved the chance to check out such a classic car as well! We plan on having Ginger outside of our larger reception in the fall for our guests to enjoy. We highly recommend Daniel and Ginger! Thank you for being a part of our wedding day!

Jerzy Banasiak

Any fan of Porsche knows that the Cayman R is a rarity, even more so in this Peridot Metallic green exclusive to the R. After just one day with the car, I was beyond impressed with it. I feel like the 911 after the 997 has gotten too big & bloated of a coupe. This thing feels perfect in size, similar to my 996 Turbo. Obviously, this is a different experience as a mid-engine NA RWD car versus a rear-engine turbo AWD car. As for the chassis itself, it is remarkably neutral despite not being exactly 50/50 weight distribution. This is down about 400 lbs from a 996 Turbo, and I could feel the extra agility as a result. Going through the twisties was effortless, and the car rotated exactly how I wanted it to. It was very predictable how the tires got loaded up and the weight shifted around. Unlike a 911, I feel like you'd have to try REALLY hard to upset the chassis and lose control. And while obviously this does not have 4 wheel steer, at times it sure felt like it with the way the rear of the car tracked my inputs from the front. It does have "only" 330HP, but the power delivery has a surprising grunt to it once you get up in the rev band and the howl that comes out of the R's pipes is absolutely intoxicating. Finally, special mention for the seat. Sweet baby Jesus, this is hands-down the BEST seat I've ever sat in. To the point I regret doing so as I want one now for my 996 Turbo. It kept me locked down the whole time no matter what I was doing, and yet it was unbelievably comfortable. I didn't know a race bucket seat could be this good. I see now what the car journalists meant that the Cayman R is one of the best balanced Porsches ever made. It also fits the island with the gorgeous color and making mincemeat of the great driving roads while still maintaining enough compliance to the point of being a worthy daily-driver. If I lived on Maui, I would likely swap my 996 Turbo out with this. Fantastic car, highly recommend it for anyone to see what a modern Porsche SHOULD feel like.

Rent a classic car in Chicago | DRIVESHARE

Capture the thrill of Chicago