Used convertibles for sale near Sleepy Hollow, IL under $899,990

I had a great experience at Autos of Chicago. The team treated me with respect and made the entire process simple. They were honest about the car’s condition and offered a fair price. My vehicle runs perfectly, and I appreciate their professionalism. I would definitely come back and recommend them to anyone looking for a used car.

Most reliable and usefull car I've had as a daily driver. Everything in the interior is placed where it should be found functionally. Power, while not a muscle car, is more than adequate. Gas mileage is excellent. Adjusting from Comfort to Sport make a very noticeable impact on the driving experience from gear shifting to steering...

Best car buying experience I ever had at Auto house motors. Martin was my sales guy he was very helpful and responsive and exceptional in finding me a great car that is mechanically sound and under my budget. Car is excellent even after a month of driving. I will definitely recommend this place and will come back again if I am looking to trade or buy another car. Thank you Martin!

Just sold mine after owning it for eight plus years. While I loved the looks of the SLK and I did enjoy owning and driving it, I was never that crazy about the spartan interior. For a Mercedes that cost $40K new, I thought it was rather plain Jane. I also wasn't happy with things like the door panels delaminating, the dash finish scaling off and probably most of all, the dang roof...I expected better from a Mercedes Benz. The roof went kaput three times while I owned the car and I got sick of the bother and the cost to deal with it. I would have also hoped it would hold its value better. I sold it rather cheap despite having put thousands into it. It's a cool little hardtop convertible but if you buy one, beware...be prepared to sink some $ into it.

Wow so impressed amazing customer service. Great cars must visit they go over and beyond to make you happy and satisfied.

Surprisingly an excellent value for sports car. Bought mine used and quality is still intact. The reliability has proven to be very good. A fun DIY car that is easy to work on. Parts are priced reasonably well and readily available. The Mercedes roadability is the true fun factor. Classic Mercedes styling, being a unique hardtop convertible, and name, will win many over now in and in the future.

I just bought a 2019 Mercedes-Benz CLS 53 AMG from Chicago Auto Place. I'm out of state but deal was great. Took about 5 days to get delivered. Longer than i wanted but they delivered. Kept communications the entire time. Ricky was great. In the process i got worried and started researching. There are some people years ago that didn't review well. I really don't thinknthe deserve those reviews. After i got the car i asked the owner about them. He said they changed their business modelnto higher end cars with lower miles. And it has worked for them. I am 100% happy and have a stellar car. Inwould recommended whole-heartedly. They are in Chicago and i amnin Texas. Stressful buying online but they delivered on all cylinders.

I love my 300C with the AMG Package. You get a much sportier look and drive. The car rides very comfortably in Comfort Plus but you can put it in Sports Plus and it becomes a whole different car. It feels like the car stiffens up and the Torque is immediately right there. Also, the AMG Package comes with great brakes! At this price point, you're going to hear a slight wind noise at higher speeds and the back seats don't have a lot of legroom. But, as an entry-level Mercedes, this is the best Mercedes for value in my opinion.

This has been the best car buying experience I've ever had in my life. No haggle prices everything is in black and white inspections are already done, the friendliest staff and owners I've ever came across. We definitely recommend them to everyone!!!!!

Bought this car after my wife said she missed her old Solara convertible. She loves it. Drives well. Extremely comfortable. Only complaint so far is that the trunk is small—and with the top down it’s almost non-existent. Her golf clubs ride in the front seat. We’ve only had it two weeks, so can’t comment meaningfully on reliability. But she loves it.

Our new car buying process was good. Questions answered and explained well. Our sales associate, Conner Keebaugh, was very helpful and patient through the process.

My baby name is Sunshine. The color I was showed was not the color I got. I love blue when I saw the blue it was different, It didn't pop, I was still like ok whatever, as long as it's blue, she'll grow on me. Before I get her I had only seen one a few yrs back and was puzzled like a buick with a rag top?? Is that a convertible?? Anyway, fast forward... usually when u buy a car u start seeing a lot of them. Well, I didn't so I'm looking at cars (waiting on the delivery of mines) I finally seen the blue I was getting and I was like, ok that's cute. The day of my new arrival. Omg she was more beautiful in person and the Blue was NOT the blue I thought. She popped!!! This baby is beautiful and rides so smooth I wanted something different and she has not disappointed me at all she had 15,910mi I've had her for a lil over 6mos. She sitting at 25k now. Absolutely no regrets i am her third and prayfully her last owner.

Amazing experience. Made the process so simple for me to get what I want. Would definitely recommend to everyone

What can I say ? It?s a Ferrari! Absolutely the best sports car on the market. They have outdone themselves

Purchased a used Audi recently and was very happy with the sales person, Sabina. She was patient, knowledgeable, and communicated very well (responsive). Ended up financing because we were out-of-state buyers. The finance manager was fantastic and worked quickly. She was also very knowledgeable and helpful. Here’s why I only rated 4 stars - there was some sketchy deferred maintenance that was not addressed prior to offering the car for sale. Notably mismatched front tires and 4mm rear brake pads. The dealers own tech inspection sheets noted the need for immediate attention to the rear brakes, but they were not replaced. Mismatched tires, in my opinion, are also a safety issue. I can only imagine these issues were not addressed to maximize profit and that’s okay as long as the car is priced right. And it was, BUT I can’t imagine a less than 2% change in price would have stopped a sale. Safety is paramount.

Bought used and owned for over a year now and this car is amazing! smooth ride, great fuel economy, luxurious and very well crafted. I have been in an accident with this car and it held up very well and is a super sporty yet safe and practical car. 10/10 would recommend!!

I had a great experience at Star Auto Works! The staff was friendly, professional, and ready to help. They took the time to understand my needs and helped me find the perfect cars within my budget. The financing process was also straightforward, with no hidden surprises. I truly appreciate their honesty and dedication to customer satisfaction. I highly recommend Srar Auto Works to anyone looking for a great car-buying experience!

I love to take the back roads with the top down and the music cranked. Handles and corners better than any vehicle I have ever driven.

Glenview was very responsive working with phone calls and texts. They worked hard to get me into the car I had contacted them about.

Great car, but expensive to own and maintain. Style is superb, every conceivable option and feature. Problems with computer suspension system, body hardware and cracks in wheels.

Jim was my sales rep. He was very nice and welcoming. Jim did an excellent job at explaining all the bells and whistles Volkswagen had to offer. He is definitely thorough and patient.

Always been a Porsche guy. I wanted a sports car with a usable back seat. This car exceeds all my requirements and expectations.

Just bought a 2019 Honda Odyssey from Rheya at City Chevy. Our Honda died suddenly and left us in a bit of a pickle. Rheya helped us through the buying process and even delivered our van to our house to accommodate our kids sports schedules. The whole team was kind and flexible with our budget. Highly recommend City Chevy. Make sure you ask for Rheya for a VIP experience.

Bought this car used in 2020. Amazing amount of luxury for the price point. Gas mileage was amazing and was extremely reliable, never had any problems getting serviced. Unfortunately, I got rear ended in this vehicle, but was saved by how well my car protected me. Loved my car, and I am set out to buy another A3.

Our salesman, Dan was great to work with. He was patient with our needs and we had an overall pleasant experience. Nice selection of vehicles as well as a clean and organized dealership.

Sexy, sleek, fast, handles amazing, classy, good gas mileage, everyone stops to look at her!!! I've never driven anything so nice. I usually like muscle cars however reaching age 50 I wanted to go in a different direction. I m so happy I did it fits everything about my lifestyle.

I worked with Regis on a 2000 Corvette and can say it was the easiest buying experience. I’d asked to have the front fender alignment looked at and he had it fixed along with a missing trim piece. The car was in excellent shape and all modifications were disclosed. He’s very knowledgeable and easy to work with. Pricing was very fair and I was in and out within a half hour on the day of pick-up. You can tell he genuinely enjoys the work he does and it shows. Thank you Regis and everyone at Illinois Motors for helping me find my dream car.

A few concerns to address, the first is ABC active body control is a concern for this car. I own Phone Doctor in Frederick Maryland and hardware tech is my passion so I want to give my feedback. I love the classy lines of the exterior. The interior is equally elegant and tasteful without gaudy disco lights. I was mesmerized into test driving a 2005 SL500 because my daily driver is a 2001 Mercedes s600. The audio system is lackluster, next weakness is the headlights, but the biggest problem is the ABC (active body control) hydraulic suspension. The audio system is disappointing and leaves me feeling flaccid but I’m used to twelve inches of JL systems shimmed into my high school hoopties. The audio system is not the deal-breaker for this $90,000 machine. And the mediocre headlights can be remedied with aftermarket auxiliary lights. The biggest weakness is the high performance suspension system. Mercedes likes to call it ABC (active body control). The hydraulic pump, seals, and mechanical moving parts gets weak and loses its performance anywhere between 80,000 to 150,000 miles. It’ll cost just as much to replace the ABC system than it does to purchase your 2nd hand sl500. If you’re in the market for one make sure you have an extra $20,000 in socked up before you drop your drawers and plop $15k on your first SL500. A dream ride with one last caveat: This car will draw a lot of attention from single ladies!

Felt welcome as I entered the door. Staff was available and when I asked for the sales person that I had been communicating with, salesperson was waiting.

I love, love, love my new Cooper S convertible! She is paying for herself in compliments already. Literally everywhere I go, someone stops me and says "your car is so cute!" She is so fun to drive and it isn't even convertible weather yet lol. I ordered black on black and I couldn't be happier with the aesthetics and performance! I hope she and I have mini happy years together!!

Autos of Chicago truly impressed me with their exceptional customer service and professionalism. From the moment I walked in, the staff greeted me warmly and took their time understanding exactly what I needed. They showed me several used cars, explained their features clearly, and were completely honest about pricing. The car I chose was clean, well-maintained, and fairly priced. The entire process—from test-driving to paperwork—was smooth and stress-free. I’m extremely satisfied with my purchase and highly recommend this dealership to anyone looking for a reliable used car.

Had the car for four years only had to do basic maintenance like tires an front brakes rear brakes tcase transmission service rear diff. Driven the thing like 65k in those four years perfect for road trips handles pretty decent in the snow an ice, you can tell it's a little heavy going down hill but the trans in snow mode does it's wizardry magic an can keep you going slow. Uphill is a little more exciting in the snow due to the rear wheel bias on the 4matic system but once it kicks the rear end out it reels it back in. It definitely likes the colder air I don't know if it's the intercooler being heat soaked but living somewhere where it's 100 plus in the summer I can tell it's not as peppy versus the winter time when it's in the teens. Interior has held up great with kids. Only thing that's broke on the inside is the springs for the cup holders an the trunk button which wasn't my fault had a friend driving it an they pulled it to hard. The exterior is honestly timeless you can't tell it's a four year old car not to flashy or dull it's a suttle boujee. The service at Mercedes has always been super, everyone thinks you're going to pay an arm an a leg for service but honestly only having to go in once maybe twice a year it's not terrible versus every 5k on other cars I've owned. The factory warranty ran out but Mercedes offered extended for an extra fours on top of the factory unlimited mileage bumper to bumper so they give you peace of mind an it makes you feel like they have faith in their own product to give you unlimited miles. In all the experience has been exciting the turbos spool up quick an gives you a little stu stu, from a dig your pretty quick, when you down shift the exhaust gives you some pops an bangs. Interior looks nice don't really think it'll age terribly considered everything now a days comes with giant screens. An as a technician for a different manufacturer it's not terrible to work on. I would recommend it to anyone.

I can’t express enough how truly grateful I am for Ahmed at Auto House in Downers Grove, Illinois! From the moment I started having issues with my first car, Ahmed showed incredible kindness, patience, and dedication. He didn’t just help — he genuinely cared about making things right and ensuring I was happy. He went the extra mile to get me into a beautiful BMW that I absolutely love, and made what could’ve been a stressful experience feel effortless and positive. It’s rare to find someone so honest, professional, and compassionate in the car business. Thank you, Ahmed, for treating me like family and turning a challenge into such a wonderful experience. I’m forever grateful and will always recommend you to everyone I know! 🙏🚘💙

My purchase experience was made so easy and efficient by my salesman, Daryl Miranda at Autonation Honda Sanford. I highly recommend both if you're looking for a professional and quick purchase experience! Go check them out!

Great site with an excellent selection of cars. The entire process was smooth and hassle-free, and I was able to buy with complete confidence. I highly recommend this site to anyone looking for a quality vehicle.

My first car was a triumph spitfire. I am a huge fan of the two seat roadster. I'm an even bigger fan of a hardtop convertible. I am not a BMW fanboy. I wish this car were not a BMW. I bought it because it's beautiful and when I drove it, it made me freaking happy. 300 plus horsepower, I've never even felt the need to put my manual transmission 35i in sport or sport Plus mode. The thing is gorgeous top up or down, a blast to drive, and often over neglected is that all four Windows go down making it a pillarless coupe with the top up. Flawlessly reliable in 14,000 miles, cockpit is tight if you put it on a few extra pounds. Such a beautiful beautiful car. Mine's a 2014, and every single time I go out someone comments about it. Unfortunately, when you're driving it people aren't as friendly because it's a BMW. Best roadster I've ever owned in a very long line of roadsters

Great car for every day commute + sports days . I live in Florida love dropping the top and zipping in the am + during busy times of day. Sexy car elegant in and out. had a 2015 model and now upgraded to 2025 and still loving it although soft top

My experience at Autos of Chicago was truly impressive. The team was professional, patient, and never made me feel rushed or pressured. They walked me through the features of each vehicle and helped me choose one that matched my expectations. The pricing was fair, and the paperwork process was quick and organized. I left feeling confident and happy with my purchase. This dealership is a great choice for anyone looking for quality used cars and excellent customer care.

Not a daily driver. But, by far the most fun car I’ve ever owned. Bought a 2013 S MT in 2015, still can’t part with it in 2024. This one’s a keeper. It is a pure joy to drive, mostly top down but even top up, the flat 6 boxer engine sound is incredible. Handling is superb - it’s like the car is an extension of the person driving it…the car goes where ever you want it to go effortlessly and nimbly…it’s amazing! The 981s MT is an incredible value. One of the best purchases I’ve ever made.