Used convertibles for sale near Midlothian, IL under $899,990

I recently sold my 2014 Corvette Z51 to Diamond Motorwork, and the experience was outstanding from start to finish. I worked with Luke, who was incredibly kind, patient, and professional. He made the entire process seamless — even going out of his way to meet me at my workplace to pick up the car and finalize paperwork. His flexibility and attention to detail made it easy to choose Diamond over other offers. The price was fair, their reputation solid, and they took the time to ensure I was comfortable with every step. I especially appreciated how Luke worked around my schedule and kept everything stress-free. The owner, Rami, was also very attentive. While Luke handled things so smoothly that Rami didn’t need to step in much, he was present and supportive throughout — especially when I requested a wire transfer instead of a check. That extra layer of reassurance gave me real peace of mind. If buying from Diamond is anything like selling to them, I’ll be stopping in there first when it’s time for my next car. Highly recommend Diamond Motorwork for anyone looking for a trustworthy, respectful, and hassle-free automotive experience.

2002 BMW Z3 Coupe (clown shoe) owner. Could be happier with my car. It’s a non-M model (only bmw that factory made more M than non-M models). I’ve got 188k miles on the dial. Truly a blast to drive. It’s quick and light, handles great and different than most cars on the road. People ask me what it is all the time. The coupe has been reliable and no major issues, just maintenance. I’ve owned it 4 years, mainly my daily driver. I’ve put about 40k miles on it. Great for short trips and canyon runs. Lots of room for groceries, I’m 6 ft tall and it’s a comfortable fit.

Had a fantastic experience with Motor Cars of Chicago, Seraj “Raj” Abughoush was amazing to work with. He was attentive from start to finish. I am an out of town buyer and Raj worked with me to make sure I was satisfied before and after purchase. He followed up timely and walked the vehicle with me via FaceTime twice. He took me on a drive via FaceTime and even found a chip in the window and had it fixed before delivery. I will definitely buy another vehicle from Motor Cars of Chicago, they have a customer for life. The manager was also highly engaged And customer focused. I highly recommended and customer friendly. Thanks Raj and team.

I've owned MB AMG, Audi R8 V10 plus and 570s. The 570s is by far the best. Great driving experience and all the luxury of the others as well plus the doors are killer.

We bought my wife c300 4matic over a year ago from Paul and when we were looking to buy another car for my son we went back to Paul he ended up getting another C300 4matic .Paul makes it easy to buy cars .I'll be buying my next car from Paul thanks again !

This was my 5th BMW but my first 6 Series and clearly the most fun car I have ever owned. I bought my 2007 650 Convertible pre-owned (1 previous owner) with 19K miles in 2010. Here I am over 13 years later and at 225K miles (yes, you are reading that right)... and still in love. I have taken very good care of it and did do an engine replacement a few years ago at 180K miles with a preowned engine because of the smoke exhaust, but was well worth it because I was not nearly ready to let this car go. At the time I believed that was either going to end up being the worst decision I have ever made...or the best. Feeling good about that $8K right now because the car is truly a joy to drive and rides like new. One caution: the run flat tires are VERY fragile and VERY expensive (over $500 per tire). If you are buying this car from a dealer I highly recommend purchasing the BMW wheel and tire warranty program or plan on replacing those tires with a quality non-run flat tire. Magnificent styling with great lines and a quality ride. Have fun!

We had a great salesperson - Elliot S. and he was very helpful, and Al P. was great for the financial portion. Both worked hand in hand to make a great buying experience!

In 2002 they sold over MSRP adjusted for inflation @$54K in todays money- pricier than the 2002 Corvette and sold like 30,000 that year. I think that new car buyer had to probably be searching for the 1955 Thunderbird experience to shell out that kind of cash, and most people born on the 60’s and 70’s just didn’t understand that appeal. Oddly, the demographic that did BABIED their cars, kept up maintenance, have all the original tools and covers (just try and find that T-handle wrench for the hard top for example) when you get lucky enough to get a shot at buying one of these babies cars you’ll find they’re sharp and quick, amazingly so despite what people someone lent one to to write about said 20 years ago. Shod with 17inch tires 🛞 and solid suspension, people can complain about the horsepower being light, but stomp it and it will jump, zoom and weave solidly with the best of them. My drive home from buying this car was a blast. Will other sports models eke out slightly better speed, power and performance over these 20 year old T-birds? Sure, why not. Does it matter if you’re not at Road Atlanta? No. For me, this a sleeper sports car that’s about to bust onto the scene and see its reputation finally living up to the 2002 Car of the Year Award Motor Trend gave it. I think you need to find one of these babied sweethearts like I did. It’s a blast to find a good one and discover what an under rated blast it is to drive. Can’t really call it super nimble, but I respect mines solid ride and reasonably quick response & rocket like performance. The incredibly clean lines scream style visually and I suggest that a 2 tone leather optional interior is worth an extra $1K (over the basic. $11-12 K value) a hard top/rack/tonneau cover intact is worth another grand. ($13-14K total seems fair generally for a babied one). Check the rubber suspension parts underneath (inside the front wheel well behind the tire) is the easiest one to check quickly for rot w/o getting under the rear).

Jim and James father and son very professional duo I want to thank you both so much for working with me and being so present in your jobs. Thank you both so much.

Toni Price (Sales Associate) from Heritage Motor Company, was AMAZING! Actually the entire staff was great. Great communication, easy buying process, well worth checking out if you are interested in a vehicle.

I contacted the dealership online on a SUNDAY (when they're closed) and Mia emailed me that same day. I went in that Monday, did a test drive with TIM (awesome guy) and left with my purchase. I did a trade-in, but forgot a few personals left in my old car. Contacted them once again, Mia said to come get the things I had left behind, so I went in and MAVERICK (another awesome guy) had took care of me as far as that. Real genuine people and I am very pleased with my Toyota Highlander.

Just had the experience of my lifetime.. Bought a 2008 VW Beetle,, black with tan leather interior, all the bells and whistles on this 30k convertible. Great car loved by his previous owner and now by us. He looks and drives like the day. He rolled off the assembly line.

Barry at Icars of Chicago has been phenomenal since day one, and he truly shines even a year after I bought my car. When I reached out with a follow-up issue, he didn’t hesitate—he jumped in, listened carefully, and helped me get things sorted quickly. It’s rare to find a dealer that stays engaged long after the sale, and Barry embodies that in every interaction. What stands out most is how they stand behind what they sell. I felt supported and respected from the moment I walked in, and that commitment hasn’t faded over time. The team’s customer service is second to none—honest, responsive, and genuinely invested in making sure you’re happy with your purchase. Their focus on building long-term relationships, not just closing a deal, is the best I’ve seen anywhere. If you’re shopping for a car and want a dealership that treats you like family while delivering real value and ongoing support, I’d absolutely recommend Icars of Chicago and Barry in particular. Their customer retention is unmatched, and that peace of mind is priceless.

I had an eye on this car for years and was finally able to purchase it pre-owned from the Lexus dealership with 81k original miles. I have had it for 1 year now and I am happy. For its age, it is a very Comfortable ride, powerful V8 engine, Reliable, and still in great condition. I have replaced the ML factory sound system with new speakers, sub and amp. Overall Love this ride. Hoping to have it for many years to come.

Great job in and out. IT'S been a good experience so I will let people know.

This car is so much better than I ever dreamed it would be. Power all over the rev range, handling like no other and comfort on top of everything else.

I turned into Continental Ferrari dealership before getting on the expressway because I was having an issue with my tire (the lug nuts were loose). Greg, Sean, and Jeff assisted me. What a great team! I had no intention of purchasing a car, yet they were still concerned with helping me.

The general manager, Anthony was very polite. Help me out find the right car and was very patient

This is the 2nd SL class I've owned, so ill try to keep this objective. These are state of the art vehicles with features way ahead of their time. They are built straight forward and repairs can be undertaken by the owner more than one would think. If you can find one in a salvage yard, you can learn how things come apart with little risk of damaging your own. The value of the experience sometimes outweighs the time it takes to learn. If that makes any sense... This car is easy to love, who wouldn't? Neck breaking acceleration, sexy good looks, the way it cradles its occupants, and surrounds them with luxury appointments unmatched by other maker's offerings. The feel is rock solid at the wheel and pedals, despite how heavy the car feels. More than enough ponies, to confidently pass or merge, and brakes that could stop a semi-tractor. The gauges are well placed, and logical information comes at your finger tips with the multi-function steering wheel. The cockpit seating seems to have an Infinite number of positions, and the easy exit feature will undoubtedly preserve the leather of the lumbar lobe. Controls are semi-ergo friendly; however the roll bar and hard top controls would be better positioned anywhere besides directly under your elbow. Concealing the roll bar up/down switches beneath the top control, does not demonstrate forethought by MB engineers. Driving the car is truly exhilarating, top up or top down. The sound remains with BOSE, and a disc changer allows for more choice. Staggered wheels are staple with the MB roadster, and improved with 35/40 series width adding to the nimble agility already demonstrated by the car. So... What's to hate? Depreciation! I feel sorry for the 1st owners of an SL. At the same time i envy that they can take it in stride. If it were not for these brazen buyers, i would never be able to afford this car. Repairs and failures... Fortunately, I've got advanced wrenching ability or this car would keep me in hock up to my neck. Although the hard top is a mastery of elegance in motion, it is delicate and prone to failure. The deck lid/boot cover/trunk lid, can present quite a challenge when, (not if), the latch fails. There is literally no way to get at the repair w/o creating damage in the course of gaining access to the latch assembly. I ended up designing and fabricating a tool that can reach the manual release levers from the rear of the cockpit. This body style incorporates a fuel cel that has an internal problem. A baffle becomes disconnected and creates an obnoxious clunk at the storage bulkhead. The fix is said to call out 18+ hours of tech time to remedy. (Ouch!) The bottom line is: you take the good with the bad, and hope that you can DIY when the time comes for repair. Till that time...enjoy the love.

I had a good experience with Chris Price awesome sales man.. no pushy sales tactics.. he was honest and straight to the point.. I have bad credit.. and was turned down from alot of different dealers Marino, Hawk,Naperville and Shermans.. all said No.. but Carmax have me thre car I wanted wth super low miles.. Thanx Chris you a good guy 🤗

Not built for comfort, built for speed. The CS interior is minimalist. When you slide into it, there’s no question what you are there for. The car will snap your head back and paste you up against the door panel—“Freude am fahren”—form follows function. Like they said of the Spitfire in the Battle of Britain, you don’t sit in it, you wear it.

Kyle got us the vehicle we wanted at a reasonable price. We were able to drive the vehicle home the same day.

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.

I purchased a 96 Caprice from this dealer.....buying experience was top notch. They answered all of my many questions about the car, negotiated price with me and had the car delivered in record time. The vehicle arrived in an enclosed trailer, was clean and ran perfectly. There were no issues with the car that I found. Normal wear and tear for a 21 year old car but very clean and taken care of. All systems worked as advertised. Top notch vehicle and dealership

Under the rear seat it leaked water from the outside when driving in rainy conditions. I upgraded the stereo system and it was better for listening to music on the interstate and hi ways with the top down. I’m hoping to find another car soon.

Dominic was great. Explained everything to me about the car and kept me updated.?His customer service was above what I expected. He took care of everything and had car shipped from Illinois to Texas. Just a pleasant experience. Need more salesman like him. Great service and great personality a true professional

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.

I haven't seen a car yet but the sales person I spoke with was cordial and accommodating

My 2008 Touring Sebring is approaching 16 years and it’s been the best. With only 129,000 km, the only repairs have been 2 brake jobs and new tires. It is comfortable and very reliable. The only down side has been the inevitable spots of rust due to the salt placed on our maritime roads in winter. I undercoat yearly and remove rust when I notice it in a body shop. Love this car 💕

I found the car I was looking for online at Zone Motors and dealt with the general manager Ray. He was very responsive to my questions and provide all documentation quickly. He assisted with my online car purchasing experience. He was accommodating to my selected auto appraiser who inspected the car and was very honest and up-front on the condition and state of the car. We reached a fair price and he assisted with completing the sale quickly. There was no pressure or issue with getting Ray on the phone or email requests. After the sale he was very responsive to questions and assistance with the shipping and paper work process. This was one of the best car buying experiences I have had in over 25 years and 5 vehicles.

Mine is a forest green / tan top convertible with a manual tranny and LT4 engine. With 41 K on the clock and a boat load of oil change tickets in the console, I think it's got a lot of life left. Paid $20 K and have no regrets.

First on the list ! Kevin what a great guy...helped me all along the way, I bought a 2000 Plymouth Prowler with matching Trailer, absolutely stunning hotrod. I flew out from Up-state NY to view the car, they handled my transportation to and from the airport...at i might add there expense, they are all very processional know there vehicles they sell and no B/S no lies, they tell you what it will cost no hidden fees. These guys are top notch. i will purchase my next hotrod from them. I would recommend this place to the president. AWESOME thank you thank you thank you guys !! your excellent in every detail of the purchase. Cant wait to get my next one there. !!! they ship all over the world. keep selling guys. love this hotrod. Thanks again Kevin and the staff !!! Norm & Kathy Shaffer Up-State, NY

The Ford Mustang is the kind of car that you get because you want, not because you need. And this one is exactly what I need. Much more ruggedly built the Fox body Mustangs, Though a little smaller in appearance, but a whole lot of fun for the money especially if you can find 8 cylinder with low mileage.

My experience was extremely pleasant and Jake was very helpful and he worked efficiently and got me out in a timely manner!

By far the best Mercedes I have ever owned. I might say the last of the real Mercedes. 2015 SL400 may be the last real Mercedes.

This dealerships customer service was a wonderful experience. My sales rep was Paul who was very attentive and responsive to any questions or concerns that I had as a consumer especially being an online sale.

easy to drive,fun car with top down plenty of performance.classic body style should hold its value and appreciate over time. great collector car . buy it.

I have never bought a car online before let alone bought a car without even seeing it or driving it. I saw a Bentley Flying Spur for sale at Chicago Auto Gallery. I called and spoke to a salesperson named Steve. From the first hello on the phone until we closed the deal and the car was shipped to me Steve was fantastic. He did everything possible to ensure that I was satisfied with the car and the deal. Now here's the extra part that I was even shocked at myself. Once I got the car, I drove it and after 5 miles some of the lights came on such as check engine, ride height, traction control and ABS. I was initially immensely pissed. I called Steve and said you might want to get ahold of that driver who delivered this car and tell him to take it back. Steve suggested I take it to a certified mechanic near me and have it looked at to see what was the problem. Apparently when one light goes off, it triggers more lights to activate. I had it looked at and to fix the car right it was going to be over $3000. Steve took care of it and the dealership paid the whole bill. In my mind that was the most solid thing to do and he did it. He could have argued and tried to avoid it or said no, you bought it, you fix it. They did not do that to me. I'm in Pittsburgh and they are in Chicago. I know I had rights and could have just sent it back but I wanted that car and they fixed it for me. I appreciate everything they (Steve) did for me and I would definitely purchase another vehicle from them. Thank you again Steve and Chicago Auto Gallery.

I have my 1999 CLK 320 Convertible for 12 years , It is great car , fast, comfortable , stylish , good gas mileage , has 12 sparkplugs , 2 for each cylinder ,if you live in a city with good weather like where I live in San Diego,CA you will gett great experience with convertible car ,my top is down most of the year.