Classic car rental in Chicago, IL
Discover the Turo car rental marketplace
- Car rental
- Classic rental
- Chicago
Extraordinary selection
From standard cars to supercars, find the perfect car for any occasion or budget
Liability insurance included
Third-party liability insurance comes standard, and choose from a range of vehicle protection plans
Easy airport pickup
You can skip the rental counter at 100+ airports across the US and Canada
Rental cars in Chicago
Average daily prices for a 3-day trip
Classic car rental Chicago for unforgettable Windy City drives
Chicago captivates with its towering skyline, world-class architecture, and vibrant neighborhoods stretching along Lake Michigan's shores. You'll discover the city's rich history through its stunning buildings, from Art Deco masterpieces to modern marvels that define the downtown corridor. The expansive metropolitan area offers everything from bustling cultural districts to serene lakefront parks perfect for exploration. Renting a classic car elevates your Chicago experience, letting you cruise the iconic streets in vintage style while accessing both downtown attractions and suburban gems. Your classic rental car becomes the perfect complement to this architectural wonderland, turning every drive into a memorable journey through America's heartland.
Recent reviews
My wife and I rented for our wedding anniversary weekend and had a great time! Oszkar was nice and helped us when we needed it. Definitely recommend!
We used this car for our wedding get away, the host was amazing and very easy to work with. The car ran great all weekend without any issues, was spotless when we picked it up and ready for photos. It was perfect for our special day! Would highly recommend this car for special occasions, or a fun weekend.
Tom was absolutely phenomenal from start to finish. The Mercury Comet was beautiful, in amazing condition, and made my daughter’s prom night feel perfect. The pictures turned out incredible and this was truly the highlight of her experience because this was the one thing she really wanted. Tom was kind, professional, communicative, and made the entire process smooth and stress free. One thing I really appreciated was the detailed video he sent ahead of time showing us how to operate the vehicle. Since it’s a 1963 classic car and we aren’t familiar with older vehicles, that extra touch meant so much and helped us feel fully prepared and comfortable. You can tell he genuinely cares about his renters and takes pride in his vehicle. We are so grateful he’s on Turo and we will definitely be renting from him again. Highly recommend.
Very easy pickup and drop off. Was a perfect way to end our wedding. Would definitely rent through them again.
A unique opportunity to rent the ICONIC Toyota Land Cruiser FJ40 that was imported from the Japanese market. The steering wheel is on the right side, so you’ll be shifting the 4-speed manual with your left hand. This dijon mustard Land Cruiser will get attention EVERYWHERE you go. The little diesel isn’t fast, so plan ahead and stick to the slow lane. What a joy to experience something most people have no access to. I will rent this again! Jonathan made the rental very easy and walked me through the features of the vehicle.
True 1986 driving experience! Glad the weather was in the 70s during my trip. Truly a car you rent if you’re trying to experience LA in a classic, manual, bare-bones car; I loved it. So nostalgic.
I rented Shawn’s 1966 Ford Mustang for my wedding, and it was an absolute dream! The car was in immaculate condition, well-maintained, and drove beautifully—an iconic classic that turned heads everywhere I went. Shawn was a fantastic host, providing clear communication, flexible pickup and drop-off, and a genuine passion for his car. He ensured the entire experience was seamless and enjoyable. If you're looking for a classic car rental that delivers both nostalgia and performance, this Mustang is the perfect choice. Highly recommend renting from Shawn—I'll definitely be back for another ride soon!
Car was absolutely amazing. We used it for our wedding and the photos turned out amazing. Was a great way to see the city. Huge thanks to Shawn for making the process so easy.
This is an amazingly fun automobile - but - do not rent it unless you're OK getting your photo taken. We were mobbed by photographers in Monaco, Eze and Cap Ferrat - the combination of the car and my stunningly beautiful wife. Arthur was tremendously helpful. Thank you! It's just terrific memories made.
Everything was perfect. Gracious hosts. I showed up a few minutes early and saw Dieter cleaning the glass in anticipation. Would not hesitate to rent from them again.
The car was absolutely awesome and so much fun to drive. The whole process of getting it from them was seamless and they showed me how everything works and I will definitely rent that car again.
Car looks Amazing. Everything works. We rent it for photography and it exceeded our expectations. Incredible experience. It was my girlfriend’s dream to drive old Mustang and perfect moment for me, to ask here for a hand 😅. Host was really helpful and friendly. We had a little chat with him and he seemed to be nice person. Definitely recommend him and his car.
Great ride with zero issues! Hadil was a great host and would recommend! Thanks again for the great weekend experience!
Awesome! Great service! Very pleased. Will rent it again. No doubt.
Wonderful experience. Barry was kind, professional, and flexible throughout the entire rental process. I will definitely rent from him again. Awesome person, awesome cars.
Amazing ride! Great service. The car is in great shape and really enjoyable to drive
C'était une très belle expérience Vraiment on n'a pas regretté de louer ce bijoux Merci beaucoup 🙏🙏🙏
Discover Chicago's iconic attractions and vibrant neighborhoods by car
Chicago offers incredible attractions easily accessible with your rental car, from the magnificent lakefront to world-renowned cultural sites. You can explore Millennium Park with its famous Cloud Gate sculpture, drive along the scenic Lake Shore Drive for breathtaking views, or visit the historic Navy Pier entertainment complex. Having a rental car provides the flexibility to venture beyond downtown, discovering charming neighborhoods like Lincoln Park or heading to the Museum Campus where multiple world-class institutions await your visit.
Millennium Park showcases Chicago's artistic heart
This downtown cultural gem features the iconic Cloud Gate sculpture and hosts free concerts throughout the year. You'll find convenient parking in nearby garages, making it easy to explore this urban oasis with your classic rental car. The park sits in the heart of the Loop, offering easy access to other downtown attractions after your visit.
Navy Pier delivers entertainment along Lake Michigan
This historic pier extends into Lake Michigan, offering dining, shopping, and the famous Centennial Wheel with panoramic city views. Parking is available on-site, though arriving early ensures better spots during peak seasons. Your classic rental car adds elegance to the lakefront drive approaching this beloved Chicago landmark.
Lincoln Park Zoo provides free family entertainment
One of America's last free admission major zoos, this attraction houses diverse animals in beautifully landscaped grounds. The surrounding Lincoln Park neighborhood offers tree-lined streets perfect for a leisurely drive in your vintage rental car. Street parking and nearby lots accommodate visitors exploring both the zoo and the upscale neighborhood's boutiques and cafes.
Getting to Chicago from major transportation hubs
Reach Chicago through these transportation options:
• By plane: O'Hare International Airport and Midway International Airport serve the metropolitan area
• By train: Union Station connects Chicago to cities across the Midwest and beyond via Amtrak services
• By car: Major interstate highways including I-90, I-94, and I-55 provide direct routes from surrounding states and cities
Essential tips for renting a classic car in Chicago
Book your classic car rental early on Turo to secure the best vintage vehicles for your Chicago adventure. Consider features like heated seats for comfortable winter driving, or choose convertibles for summer lakefront cruising along Lake Shore Drive. Look for vehicles with modern safety features like backup cameras to navigate the city's busy streets and tight parking spaces, while keyless entry adds convenience when exploring multiple neighborhoods throughout your stay.
Browse by category
Browse by make
Frequently asked questions in Chicago
Why choose a classic car for Chicago adventures?
Classic rental cars offer an authentic way to explore Chicago's iconic architecture and historic neighborhoods, turning every drive into a memorable experience. These vintage vehicles complement the city's timeless appeal, from cruising past the Art Institute to navigating the scenic lakefront areas. A classic car rental transforms ordinary sightseeing into an elegant journey through the Windy City's most celebrated districts.
What should you expect when driving vintage vehicles?
Vintage rental cars typically feature manual transmissions and require more deliberate handling compared to modern cars, making each drive more engaging and connected. Classic car enthusiasts appreciate the authentic driving experience these vehicles provide, from the distinctive engine sounds to the tactile steering feedback. Expect a more immersive automotive experience that demands attention and rewards skilled driving through Chicago's diverse terrain.
How to secure classic cars while parked?
Always park classic rental cars in well-lit, populated areas and use steering wheel locks or other visible deterrents when exploring Chicago attractions. These luxury vehicles attract attention, so choose secure parking facilities near popular destinations like Millennium Park or the Museum District. Consider covering distinctive features with car covers when parked for extended periods during your car rental experience.
Can classic cars handle longer road trips?
Many classic rental cars excel on longer journeys, especially well-maintained models like vintage Cadillac or Mercedes Benz vehicles that were designed for comfortable touring. These cars often provide a more relaxed driving experience on highways leading from Chicago to scenic destinations throughout Illinois. However, plan for more frequent stops to monitor fluid levels and ensure optimal performance during extended drives.
How does weather affect classic car performance?
Chicago's variable weather conditions can impact classic rental car performance, with cold temperatures potentially affecting engine startup and battery performance. Summer heat may require more attention to cooling systems, particularly in vintage luxury vehicles during stop-and-go city driving. Classic rental cars generally perform best in moderate weather conditions, making spring and fall ideal seasons for exploring the city's outdoor attractions.
Which scenic routes suit classic car drives?
Lake Shore Drive offers stunning views of Lake Michigan and showcases classic rental cars against Chicago's magnificent skyline backdrop. The historic neighborhoods of Lincoln Park and Gold Coast provide tree-lined streets perfect for leisurely drives in vintage vehicles like Ford Mustang or Porsche models. These routes highlight both the car's elegance and the city's architectural beauty, creating perfect photo opportunities for classic car rental enthusiasts.
What documents and paperwork do I need to rent a car on Turo?
To rent a car on Turo, you must create a Turo account, have a valid driver's license, get approved to drive on Turo, and be 18 years old or older in the US, 21 years old or older in Australia, or 23 years old or older in Canada. In the UK, you must be 21 years old or older and have held a UK or EU license for at least one year, or another driver's license for at least two years. In France you must be 18 years old or older and have held a driver's license for at least 2 years, longer for certain makes and models of vehicles. When you're booking your first trip, you'll go through a quick approval process by entering your driver's license and some other information. In most cases, you'll get approved immediately, and you'll be set for all future road trips, day trips, and business trips!
Is there long term car rental on Turo?
Yes there is — whether you want to rent a car for three days, three months, or even longer, you can on Turo. You'll find discounted prices on bookings lasting 3+, 7+, or 30+ days, so you can get the best deals and lowest rates possible by booking longer trips.
What kind of license do I need to rent a car on Turo?
Turo accepts valid licenses (not expired, suspended, or revoked) that allow for full driving privileges; this includes driver's licenses issued outside of the US. Licenses that Turo doesn't accept in the US include any that have expired, have been altered, are conditional, probational, provisional, or restricted. Learner's permit/instruction permits are not accepted.
How does car rental insurance work on Turo?
No, you don't need personal insurance coverage to rent a car on Turo. In the US, any personal insurance you may have that covers damage to the host's vehicle would kick in before your Turo protection plan. When booking a car in the US, you'll choose between three protection plans — Premier (eligibility requirements apply), Standard, or Minimum — to get the level of protection that's right for you. On each trip, you're covered with third-party automobile liability insurance provided under a policy issued to Turo by Travelers Excess and Surplus Lines Company.* In New York state, you'll also choose between Premier (if available), Standard, or Minimum. With each plan, you're covered with liability insurance of $1,250,000.* Protection plans for New York trips also include access to roadside assistance, priority phone support, and 24/7 customer assistance.
* Est. daily price. Search for up to date price information.