

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
Average daily prices for a 3-day trip

Mercedes-Benz SLC-Class
2018
•5.0
(13)

Polaris Slingshot
2020
•4.98
(49)

Jaguar F-TYPE
2021
•5.0
(25)

Ford Bronco
2024
•5.0
(92)

Ford Bronco
2026
•5.0
(1)

Ford Bronco
2024
•4.99
(131)

Ford Bronco
2024
•5.0
(10)

Ford Mustang
2020
•5.0
(165)

Jeep Wrangler 4xe
2025
•4.96
(29)

Chicago captivates visitors with its stunning skyline, world-class architecture, and vibrant cultural scene along the shores of Lake Michigan. The Windy City offers an incredible blend of urban sophistication and lakefront beauty, from the iconic Loop district to charming neighborhoods like Lincoln Park. Booking a rental convertible enhances your Chicago experience perfectly, allowing you to cruise along Lake Shore Drive with the top down, feeling the breeze as you take in breathtaking views of the city's magnificent skyline and sparkling waterfront.

Best car I’ve ever driven hands down, 10/10 hosts I recommend anyone to book with them!

It was exactly how it looked on the pictures… very clean;gas was fill; and an all around great car… I would book with box auto again


Kaytee was a great host, she helped us with some last minute changes to our plans and was super accommodating. Of course the car was great as well! Great experience and would be a joy to do it again!



Dorin was an amazing host with a beautiful vehicle in immaculate condition. I requested the car to be delivered to my hotel and it was done very promptly. No hassles. Thank you


5 stars. Renting the Corvette C8 was an amazing experience from start to finish. The car is absolutely beautiful, loud, fast, and turns heads everywhere you go — everything you’d hope for and more when renting a Corvette. The driving experience was honestly unreal. Rico was extremely helpful throughout the entire process. He took the time to explain the ins and outs of the car, made sure I was comfortable handling it, and made both pickup and return super easy and smooth. Great communication and professionalism all around. Would definitely rent again.

The car was great! It made me consider buying a Broncos now! I will say, it is best to add the drop off location delivery address for the next renter so in case they are running late for their flight they won’t have to look for the garage & drop your car off anywhere. I won’t rate low just for that because the car was awesome. Thank you for also providing the address to me’

Great car and excellent communication! We rent from them every time I come to the area !

Highly Recommend! Awesome Rental! Excellent customer service start to finish. Vehicle in like-new condition. Easy pick up and drop off. Would definitely rent this vehicle again and rent from this host again!
Chicago offers countless attractions easily accessible by rental car, from the bustling Magnificent Mile to the serene lakefront parks. You can cruise through downtown's architectural marvels, explore vibrant neighborhoods, and discover hidden gems throughout the metropolitan area. A rental convertible provides the perfect way to experience the city's beauty, especially when driving along the scenic lakefront routes where you can enjoy unobstructed views of both the skyline and Lake Michigan's endless horizon.
Millennium Park stands as Chicago's crown jewel, featuring the famous Cloud Gate sculpture and stunning Crown Fountain. Located in the heart of downtown, this cultural hub offers easy access from various parking areas throughout the Loop. The surrounding streets showcase the city's renowned architecture, including historic buildings and modern skyscrapers. Driving through this area in your rental convertible allows you to fully appreciate the urban canyon effect created by towering structures while enjoying the open-air experience as you navigate the bustling city center.
Navy Pier extends into Lake Michigan, offering entertainment, dining, and spectacular city views. This popular destination features the iconic Centennial Wheel and numerous seasonal festivals throughout the year. Parking is available nearby, making it convenient for visitors exploring the area. The pier provides an excellent starting point for lakefront drives, where you can continue your journey along the scenic waterfront roads that showcase Chicago's beautiful coastline.
Lincoln Park Zoo provides free admission year-round and sits within one of Chicago's most picturesque neighborhoods. The surrounding area features tree-lined streets, historic homes, and boutique shopping districts perfect for leisurely exploration. Driving through Lincoln Park in a rental convertible offers a delightful contrast to downtown's urban intensity, with peaceful residential streets and abundant green spaces. The neighborhood's proximity to the lakefront means you can easily transition from city exploration to scenic waterfront drives, creating a perfect blend of urban and natural beauty.
Wicker Park and Bucktown represent Chicago's creative heart, featuring independent galleries, vintage shops, and innovative restaurants. These neighborhoods showcase the city's artistic spirit through colorful murals and unique architecture. The area's grid street layout makes navigation straightforward, while tree-lined avenues provide pleasant driving conditions. You'll discover numerous local cafes and music venues that reflect the area's bohemian character and cultural diversity.
The Museum Campus houses world-renowned institutions including the Field Museum and Shedd Aquarium, all situated along Lake Michigan's shoreline. This cultural district offers ample parking and connects seamlessly to scenic lakefront drives. The area provides spectacular views of both the city skyline and the lake's vast expanse. Driving through this region in your rental convertible allows you to transition effortlessly between cultural exploration and scenic touring, with the open-air experience enhancing your appreciation of the lakefront's natural beauty and the city's impressive architectural backdrop.
Turo
App-based experience
No waiting in line
1,600+ unique makes & models
Get the exact car you choose
Delivery options & thousands of pickup locations
Cars rented out by local small businesses
Vehicles and hosts rated by guests
Traditional rental
Standard rental counter experience
Waiting in line
Limited selection
Get one type of car “or similar”
Pickup at retail locations
Owned by large corporations
No vehicle ratings
To rent a car on Turo in the US, you must be 18 years old or older.
Take Interstate 190 East from Chicago O'Hare International Airport, then merge onto Interstate 90 East (Kennedy Expressway) toward downtown Chicago. The route passes through several neighborhoods before reaching the heart of the Windy City. Having your own rental car provides flexibility to explore Chicago's diverse districts at your own pace.
Some hosts offer unlimited distance for a trip; others set a daily distance limit — you'll need to check on each rental car individually to see if this service is provided. On the vehicle pages, you'll see the total miles or kilometers you're allowed to drive under the heading "Distance included." You can find cars offering unlimited mileage with every trip by using the "Unlimited distance" filter.
Popular routes include driving north to Wisconsin's scenic lakes region or west toward the Mississippi River valley. The Great Lakes Circle Tour offers stunning lakefront scenery, while Route 66 begins in downtown Chicago for classic American road trip experiences. Many travelers also head south to explore Illinois' historic sites and natural areas beyond the Windy City.
Yes, several major highways around Chicago O'Hare International Airport require tolls, including the Jane Addams Memorial Tollway and parts of Interstate 90. The Illinois Tollway system accepts I-PASS transponders and cash payments at most locations. Consider having exact change ready or obtaining an I-PASS for smoother travel through the Windy City area.
A convertible car rental can enhance your Chicago experience during warmer months, allowing you to enjoy lakefront drives along Lake Michigan. Consider Chicago's variable weather patterns when choosing a rental convertible, as sudden temperature changes are common. The city's scenic routes, including Lake Shore Drive, offer excellent opportunities for open-air driving adventures.
Numerous gas stations operate within a short distance of Chicago O'Hare International Airport along major routes like Mannheim Road and Higgins Road. Electric vehicle charging stations are available at various shopping centers and hotels throughout the airport area. Many charging networks serve the Chicago region, making it convenient for electric rental cars.
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!
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.
Illinois requires all passengers to wear seat belts, and using handheld phones while driving is prohibited throughout Chicago. Right turns on red are permitted after a complete stop unless posted otherwise. Speed limits are strictly enforced, especially in school zones and construction areas around the airport vicinity.
* Est. daily price. Search for up to date price information.