

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

Ford Bronco
2026
•New listing

Ford Bronco
2024
•5.0
(92)

Ford Bronco
2024
•4.99
(131)

Jeep Wrangler JK Unlimited
2018
•5.0
(9)

BMW 4 Series
2015
•4.96
(59)

Polaris Slingshot
2020
•4.98
(48)

Chevrolet Corvette
2024
•New listing

Jeep Wrangler Unlimited
2018
•5.0
(10)

Chevrolet Corvette
2023
•5.0
(15)

Chicago, the Windy City, offers a vibrant urban landscape perfect for exploration. From the stunning Lake Michigan shoreline to the iconic skyline and world-class architecture, renting a convertible enhances your Chicago experience. Feel the breeze as you cruise down Lake Shore Drive, soak in the sun at Millennium Park, or embark on a stylish journey through diverse neighborhoods. A convertible rental allows you to fully immerse yourself in the city's energy and charm, making your Chicago adventure truly unforgettable.
I had an excellent experience with this host. She was very attentive to my requests and made sure everything went smoothly. The car was in perfect condition, exceptionally clean, and exactly as described. Communication was outstanding — she responded to messages quickly and was always helpful. I am very satisfied with the rental experience and would gladly rent from her again. Highly recommended!


Geoffrey went above and beyond to make everything super easy and never took more than a few minutes to reply to messages. And he's just a delightful person. The car is in excellent condition and simply one of the best driving experiences ever. The performance, design, comfort, and above all, the engine soundtrack make it truly unforgettable.

As a host and a passionate driver, I have to say the Mazda MX-5 embodies what a true driver’s car is. Engine in the front, power to the back, and a manual gearbox—this is pure, authentic connection to the road. The magic happens between third and fourth gear on a curvy road—you feel completely one with the car. While the tires are a bit narrower than a Toyota 86, that only makes it more agile—it handles like a dream. It’s surprisingly comfortable for its size, but ultimately, it’s that raw driving joy at a reasonable price that stands out. And hats off to the host—great communication and a smooth, seamless experience!

Nicholas has a great selection of cars, is reliable, accommodating, convenient location and very responsive. That’s why I’m renting from him all the time!
Great first experience from renting through Turo. Met my expectations with the jeep, amazing car


The host was very sweet, responsive, and helpful throughout the entire trip. They answered all of our questions quickly and made sure we had everything we needed. Communication was easy, and they were very accommodating whenever we needed help. Overall, it was a great experience and I would definitely book with them again!

Great trip! The car is super cute, drives well and the host is incredibly responsive.

The host was incredibly kind and thoughtful — she answered all my questions and supported me every step of the way. It was my first time using Turo, and everything went perfectly. The car was impeccable — super clean, smelled amazing, and in perfect condition. The instructions were very clear and easy to follow. The car itself is also wonderful. I was lucky to have a sunny day and could enjoy driving with the top down, which made the experience even more special. It was truly an unforgettable day. I visited several architectural sites, and being in such a beautiful and special car made it even more memorable for me. I highly recommend both the car and the host — she’s absolutely lovely.

Renting a convertible in Chicago offers an exhilarating way to explore the city's diverse landscapes. Feel the wind in your hair as you cruise along Lake Michigan, take in panoramic views of the skyline, and experience the vibrant neighborhoods in style. A convertible rental allows you to fully appreciate Chicago's architecture and green spaces, creating lasting memories of your urban adventure.
Lake Shore Drive offers a breathtaking convertible rental experience in Chicago. This iconic route hugs Lake Michigan, providing stunning views of the shoreline and city skyline. Start your journey at Oak Street Beach, cruise past Navy Pier, and continue south to Museum Campus. Along the way, enjoy glimpses of Grant Park and Buckingham Fountain. For the best experience, drive during sunset when the city lights begin to twinkle. Don't forget to stop at the many beaches and parks for picturesque photo opportunities.
Experience the trendy neighborhoods of Wicker Park and Bucktown in your rental convertible. These lively areas come alive at night with their eclectic mix of bars, restaurants, and music venues. Drive down Milwaukee Avenue, the main artery, to soak in the hipster vibe and colorful street art. Park your convertible and explore the unique boutiques and vintage shops. As evening falls, cruise to popular spots like The Violet Hour or Piece Brewery for a night out. The convertible adds a touch of style to your urban exploration.
For a romantic convertible experience in Chicago, head to Promontory Point in Hyde Park. This picturesque peninsula juts out into Lake Michigan, offering breathtaking views of the city skyline. Drive your rental convertible along the scenic South Lake Shore Drive as the sun begins to set. Upon arrival, park and stroll hand-in-hand along the limestone steps leading to the water. The panoramic views of Chicago's skyline, especially during sunset, create a magical atmosphere perfect for couples. Pack a picnic to enjoy on the grassy areas while watching the city lights come alive.
When renting a convertible in Chicago, book early, especially during summer months when demand is high. Check the weather forecast to plan your top-down drives accordingly. Consider a luxury convertible rental for a stylish city tour or a sporty model for a more dynamic driving experience. Be aware of parking challenges in popular areas and opt for parking garages when possible. The best times for open-top driving are typically late spring and early fall when temperatures are mild. Choose a vehicle that complements your itinerary, whether it's cruising along Lake Michigan or exploring charming neighborhoods.






































Chicago offers several convenient pickup locations for convertible rentals. Downtown areas like the Loop and River North are popular choices, providing easy access to the city's attractions. Guests might also consider locations near Millennium Park or Navy Pier for scenic drives along Lake Michigan. When selecting a pickup spot, think about proximity to your accommodation and planned activities. Consider traffic patterns and parking availability, especially during peak hours. Some hosts on Turo may offer delivery options, which can be convenient for guests staying in residential neighborhoods or suburbs. Remember to check the vehicle's features, such as GPS or backup cameras, to ensure a smooth rental experience. Ultimately, choosing a location that balances convenience with your Chicago itinerary will enhance your convertible rental adventure in the Windy City.
Chicago offers several scenic routes perfect for a convertible rental adventure. The Lake Shore Drive provides stunning views of Lake Michigan and the city skyline. Heading west, the Illinois River Road National Scenic Byway offers a beautiful countryside experience. For a charming small-town feel, take a drive through the historic Galena. The Great River Road along the Mississippi River is another picturesque option. Remember to put the top down on your rental convertible to fully immerse yourself in the Illinois landscape. These routes showcase the diverse beauty surrounding Chicago, from urban vistas to rolling hills and waterfront scenery, making your convertible rental experience truly memorable.
When packing for a convertible rental trip in Chicago, efficient use of trunk space is crucial. Opt for soft-sided luggage or duffel bags that can be easily molded to fit the available space. Consider using packing cubes to organize and compress your belongings. Pack versatile clothing items that can be mixed and matched to create multiple outfits. For longer trips, plan to do laundry rather than overpacking. Utilize the passenger area for additional storage, keeping in mind the need to secure items when the top is down. Don't forget to leave room for any souvenirs you might pick up during your Chicago adventure. With smart packing strategies, you can make the most of your rental convertible's limited trunk space while enjoying the wind in your hair.
When parking a rental convertible in Chicago's busy urban areas, safety is paramount. Always opt for well-lit, populated areas or secure parking garages when possible. If street parking is necessary, choose spots with high visibility. Ensure the top is fully closed and locked before leaving the vehicle. Remove all valuables from sight, including any items in the passenger area. Consider using a steering wheel lock or alarm system for added security. In Chicago's bustling downtown, be mindful of parking regulations and time limits to avoid fines. When parallel parking, take extra care to protect your rental convertible's exterior from potential bumps. By following these practices, you can enjoy your Chicago adventure with peace of mind about your parked convertible rental.
When driving a rental convertible around Illinois, be prepared for sudden weather changes. Keep an eye on the forecast and have a plan to quickly close the top if rain or strong winds approach. Familiarize yourself with the convertible's roof mechanism before setting out. If caught in unexpected rain, find a safe place to pull over and secure the top. For sudden temperature drops, keep a light jacket or blanket easily accessible. In case of extreme weather warnings, seek shelter promptly. Remember, Chicago's weather can be unpredictable, so flexibility is key. Always prioritize safety over the open-air experience when conditions become challenging. By staying alert and prepared, you can enjoy your convertible rental journey through Illinois while adapting to any weather surprises.
To safely operate a rental convertible's roof in Chicago's varied climate, familiarize yourself with the mechanism before your trip. Only open or close the roof when the car is stationary and on level ground. In Chicago's windy conditions, ensure all loose items are secured before opening the top. During hot summer days, park in shaded areas to keep the interior cool. In cooler weather, allow the roof to warm up before operating to prevent damage. Always check for obstructions before closing the roof. If rain threatens, close the top promptly to protect the interior. Remember, Chicago's lakefront can bring sudden weather changes, so be prepared to adjust quickly. By following these tips, you can safely enjoy your convertible rental experience while navigating Chicago's diverse climate.
When embarking on long convertible rental drives through Illinois, sun protection is crucial. Apply a high-SPF sunscreen generously and reapply every two hours, especially on exposed areas like face, neck, and arms. Wear UV-blocking sunglasses to protect your eyes from glare and harmful rays. A wide-brimmed hat can provide additional shade for your face and neck. Consider wearing light, long-sleeved clothing for extra coverage. Stay hydrated by keeping water easily accessible in the car. If possible, plan your route to include shaded areas or schedule breaks to escape the midday sun. Remember, even on cloudy days, UV rays can penetrate, so maintain sun protection throughout your Illinois adventure. These precautions will help you enjoy your convertible rental experience while safeguarding your skin from excessive sun exposure.
When selecting a convertible rental for your Chicago adventure, consider the vehicle's size and comfort for city driving and potential longer trips. Assess the trunk space to ensure it meets your luggage needs. Look for features like GPS navigation to help you explore Chicago and surrounding areas. Consider fuel efficiency, especially if planning extensive drives through Illinois. Check the convertible top's ease of use and weather sealing for Chicago's varied climate. If visiting during colder months, ensure the heating system is efficient. For tech-savvy travelers, look for modern amenities like smartphone integration. Consider the car's performance capabilities if you plan to take scenic drives outside the city. By weighing these factors, you can choose a convertible rental that enhances your Chicago experience, combining style with practicality.
To capture great photos and maximize your convertible rental experience in Chicago, plan your route to include iconic landmarks like the Chicago Bean and Navy Pier. Take advantage of the open top to get unobstructed skyline shots, especially along Lake Shore Drive. For unique perspectives, consider early morning or sunset drives when the light is optimal for photography. Use a secure phone mount to safely capture video footage of your journey. When stopped, experiment with different angles, including shots from inside the car looking out. Don't forget to photograph the rental convertible itself against Chicago's stunning backdrops. Remember to respect local traffic laws and find safe spots to pull over for photos. By combining careful planning with spontaneous moments, you'll create lasting memories of your Chicago convertible rental adventure.
* Est. daily price. Search for up to date price information.