Used convertibles for sale near Winthrop Harbor, IL under $25,000

I’m so happy I found my dream car so close to home! The sales team at Lux was wonderful to work with. Highly recommend buying a car here!

Absolutely a delightful to drive, superb quality interior and excellent drive! I am very pleased with my 2016 Mercedes Benz E350 4Matic! Great info center!

The staff is very friendly and helpful. They services my vehicle quickly and sent me a report with what the service check found and what they recommended

I bought a GT Premium/California Special and love it. It has more bells and whistles than any Mustang I have ever owned. The Mustang is well insulated and is a solid vehicle.

Great dealership would definitely recommend it to others staff is very knowledgeable and prices are reasonable

I have owned my pony for 4 years now. The only repair I had was a fuel pump 2 years ago. Every little button still works, it is fast(but not superfast yet) and it looks soooo cool! The main reason I went with this Mustang over a Vette, is it is way easier to get in and out of for an older guy. It has all the standard amenities you could want. And did I mention how cool you look in a red Pony convertible when you squawk the tires???

Tommy is very knowledgeable and the car was exactly as described in the listing! We will be coming back for future purchases!

Fun summer ride you'll enjoy. Top down comfort. V8, all the ponies you need to get up and go. If you like to tinker this is the car for you to add your personal touch!

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.

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 had a Wonderful experience purchasing my vehicle here! This is my second time purchasing a vehicle at Specialty Motors and Mike went above and beyond to make sure I felt heard and my needs were met with what vehicle I was getting! Very professional and highly recommend!

I've dreamed of owning a 911 Turbo since I was in my teens. I'm now 63 years old and don't need to drive 150mph anymore. Last year my wife and I decided to look for a convertible to recapture the days of when we first started dating in 1987 when she had a 1982 Fiat Spyder 2000 convertible. We traded that in 2004 on a BMW 330Xi. We had a pretty sweet deal lined up on a 2008 BMW Z4 until the day before we went to pick it up and found out the dealer sold it from under us. What could have really sucked turned into a golden opportunity: we chanced upon a 2001 Boxster S with 59,000 original miles. We have not regretted the decision one bit. Yes, the ergonomics are somewhat dated compared to today and it's not the latest and greatest technology, but we bought it to drive, not to be distracted with all sorts of gizmos. (I'm employed as a Sales representative at a local Chrysler/Dodge/Jeep Dealer for over 35 years. I'm exposed to all the technology). This little Bavarian bomber is an absolute blast to drive; comfortable, quick, sticks to the road like burnt eggs to a cast iron frying pan, and turns heads everywhere. It's capable of 160+ mph, but the right road at 55 mph brings grins all the time. We just went for a weekend trip with it and had no problem with room for our luggage, a tote bag, and a small soft-sided cooler. And as an added bonus, we took it through the famed Hawk's Nest Highway on Route 97 north of Port Jervis, NY. Wonderful to drive, comfortable even after a couple hours, fuel-efficient (except when I play with the Tiptronic on a twisty road), and so far, dead-bolt reliable. So I didn't get my 911 Turbo; the Boxster S is a more than welcome consolation prize. You owe it to yourself. P.S- My wife drives it more than I do!

Autos of Chicago offers a dependable range of used vehicles featuring popular makes and models at competitive prices. The dealership focuses on customer satisfaction, ensuring every car is thoroughly inspected for quality and performance. Their friendly team helps buyers compare options, arrange financing, and drive away with confidence.

While getting groceries out of my car, My trunk came down on my head (C-300, 2017). Sometimes trunk opens after I lock the car. This is dangerous. What is the problem?

Fast and easy experience here was greeted by Joel who was very friendly after flying in from NY pick up my beautiful bmw m5 would highly recommend!

Great driving and solid car. I especially love the handling and ride for cruising the beach. When the twin turbo hits you with that boost she is fun to drive. She gives you balanced power at the helm and take in that confidence that this lovely lady gives. Pop the top and then really take in that beach Sunset. E-450 4matic Cabriolet Excellent Ride from a classy and sassy dame.

I had an issue with my coolant that could not be identified when I went to another dealer. When I went to BMW Northfield, they were able to figure out what was wrong and fix everything really quickly. They were also very helpful!

Audi TT is perfect replacement for a Porsche 911 Reliable and racy zoom zoom All options standard with the S-package Super fun hate to sell it

Excellent experience from start to finish! The staff was friendly, knowledgeable, and made the entire process smooth and stress-free. Highly recommend this dealership for anyone looking for quality service and great deals.

My is machine silver with competition gray wheels 1lt nice car . Only problem I have had and a lot more people have had with the C6 is the automatic automatic shifter gets stuck in park. A recalled that never happened.

My experience has been awesome so far! They got me into a very nice car, for an awesome price, in less than 2 hrs, and Monique literally saved my life, lol! I would recommend this place to any and every one! Amazing prices, reliable, decent vehicles, and alot to choose from too! They will take care of you, I can promise you that!

Bought this car in front wheel drive convertible option and with just 55,000 miles. Love the performance and it gets great gas mileage of about 30 on the highway and mid-20s around town. Bought it in 2019 and hopefully it lasts until 2029!

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.

In my opinion, the 1999-2002 SL500's represent the very best two-seater convertible in the world at any price. Sure there are now metal-retractable-top convertibles, and they're very slick - however, as far as classic rag-tops go, there is nothing that beats the SL500 in all six categories... In the under $100K price-range, there was nothing at the time to beat it - the Jaguar XJS and XK8 are both nice, but the SL is just more solid, more subtle and engineered to perfection. Whether it's competing with a Porsche Cabriolet, a BMW Z8, a Jaguar or any number of other prestige-brand luxury two-seaters, the SL holds its own against convertibles even in a higher price-range, such as late-90's early 2000's Aston-Martins, Maserati's (99-2002), and even the comparable Ferrari's (355 Spyder)... To find a car more competent, fast, stylish AND comfortable is not easy - at any price. I bought a '99 SL500 with 42K miles on it - it has been just stellar. I bought in 2009 for $20K (less than a fifth of its almost $100K new-car cost). Fast, fluid, fun - and safe, reliable and efficient... People don't buy these for the gas-mileage, but they are as efficient as anything new in the same class - I get over 20mpg average, and that's with a 300hp V8... Even the brand-new models don't do much better. In any case, I cannot fault this car in any category - the styling, both inside and out, is timeless, elegant and sporty. The car rides beautifully, is hushed at all speeds, handles nimbly (especially for such a heavy car) and feels solid as a vault. Although I had to do a fair amount of maintenance to get the car perfect when I bought it (such as power-top actuators, etc.), there were no surprises, as we had the car inspected. A properly-maintained car is incredibly reliable and durable - they are built to deliver lots of trouble-free motoring, and they are just about the classiest thing out there. Although this model (99-02) is now passing the ten-year mark, it is still so modern in every respect - from performance to comfort and safety... The only thing it doesn't have is Navigation and parking sensors - two things I've never missed, as the car is a very modest size (easy to park), and it's easy to use a smart-phone for navigation... Bottom-line: the safest, most reliable convertible of this genre - a beautiful, elegant car that still holds its own thirteen years later...

I was looking for a specific car that was at this CarMax. Problem was that I live in Minnesota, not Chicago and would have to traveling a great distance for a car I had not seen other than in pics, potentially risking wasting a great deal of time and money. I had to trust Jonathan, my salesman, to tell me the condition of the car where the pics could not. He was completely honest and the car was exactly what he said it was. Between Jonathan and Adam, the sales manager i was able to close the deal and drive back to home within an hour. I am completely pleased with the car and 100% satisfied with the dealership. I guess you can trust a car dealership. I did and they did not let me down. Thanks guys.

I bought a 2016 Red E400 4Matic coupe with 49K miles on it in Dec 2023. I've had no problems with it and have only brought it in for it's once a year maintenance (I drive less than 10K a year). My only other expense was slapping new tires on it. The vehicle has the right amount of tech on it, and it's a smooth on the road and quick on the pickup when I need it. This is my first Mercedes (lifelong Toyota and Lexus owner) and can definitely say this will not be my last Mercedes.

Great service. Thank JB for excellent support. Definitely coming back . Timing and praises is perfect.

I really like my 2017 mustang Roush, The only complaints are the front bumper clips break easy and most of all the paint is less than paper thin and in 4 years was flaking off around back window it sad such an expensive car. THE BIGGEST THING IS THERE IS NO BLUE BOOK FOR ROUSH.

recently purchased a vehicle from Old Orchard Nissan, and I couldn’t be more satisfied with the entire experience. From the moment I walked in, the staff was welcoming, professional, and genuinely helpful — no pressure, just honest service. My salesperson, Jason Chu, was knowledgeable, patient, and took the time to answer all my questions. They helped me find the perfect car for my needs and made the process feel smooth and stress-free. The finance team also did a great job explaining everything clearly and worked to get me a great deal. The vehicle was clean, in excellent condition, and exactly as described. I truly appreciate the transparency, integrity, and care that went into every step of the process. Highly recommend Old Orchard Nissan to anyone looking for a reliable vehicle and top-notch customer service. I’ll definitely be back when it’s time for my next car!

Best covertible under $30k used. Italian styling/handling and Japanese reliability. What a car. As a previous 911 and SL 300 owner, I prefer this as a toy without the expensive repairs. All parts are Japanese and repairs are minimum. Best KEPT secret, buy a classic car, and enjoy for years! Handling is insane! Not a daily driver!

Mitch was excellent to work with, best experience ever at a dealer. I got a beautiful car and was treated very well. I would definitely recommend doing business with these folks.

I bought one of these a couple of years back. I even used it as my daily driver which is not for everyone if you have kids/items to haul around town. However, it was the most fun car I have ever driven, I never ran into any issues maintenance wise or when I was driving it, and I even got in a severe car accident that could have very easily taken my life. This car may not be the safest for rolling over in but it kept me safe when I hit a concrete barrier after being run off the highway by a semi.

It was very excellent. The sales representatives was very professional and curious. He went above and beyond. Even tho me and my wife live 2hrs away. He responded promptly to our calls and delt with any issues we had.

I bought the 2017 Mustang online, something I said I would never do. I was afraid the turbo charged 4 cylinder engine wouldn’t have enough power for me. I never drove one before. I couldn’t be happier. I get the fuel economy of a 4 cylinder engine with all the power I could ask for!! I love it!!

I purchase the blue 69 restomod Camaro over the internet. I had Alan Gordon as my sales representative.He was on top of it all the way . He reassured me that everything was on the up and up . Did everything he said he would . Got the car to me in California and couldn’t be happier! If they have what you want , trust is their main goal. Thanks Illinois Motirs and Thanks Alan . I would tell anyone they are great !

I purchased my 2000 C5 dark bowling green in 2014 it only had 23,000 miles on it, today it has close to 200,000 miles I drive it the only upgrades that I've done is I put different Wheels that mimic the stock ones they're just one inch wider front and back, an air intake from K&N and a Cat-Back system from Flowmasters. I can't go anywhere where at least two people come up and comment on my car and no one can believe it's 23 years old I do keep it in good shape it is the original paint. Like any other vehicle you have little issues water pumps I change the air conditioning a leak in the rear end had to get a new alternator all the normal stuff for cars that are 23 years old no major failures. The performance on this car is fantastic it's fast a Corners well. And if I can keep my foot out of it it gets pretty good gas mileage for the most part. I will say if you plan to get one of these C5 Corvettes you have to be willing to work on the car if you want it to run the way it's designed has a ton of sensors all kinds of grounds there's a lot to it, but the joy and the fun that you get out of it is well worth it.

Bought my first car here! Great deal! Nice people! 5 Stars service! They make me feel like family!

My 2008 Redline was one of my favorite car purchases ever. I bought it as a second vehicle to cruise around with the top down. This car shocked me by it's performance. Super quick with very little turbo lag. Handling is on par with a Miata. With it's massive clam shell hood it's also super easy to work on. Not the nicest interior materials, but it's reliable and parts are readily available. My opinion is this is the perfect buy for someone looking for an affordable sports car.

Autos of Chicago is committed to delivering high-quality used cars backed by excellent customer service. Each vehicle undergoes careful inspection, ensuring performance, safety, and long-term durability. With flexible financing options and helpful staff, every visitor receives the guidance they need to make a confident purchase.

This car checks all of the boxes. The color of Sepang Blue Pearl Effect is outstanding. I own the prestige trim with the black optics package and the quality is excellent. The ride is comfortable, the performance rivals most cars on the road and the luxury of leather and alcantara with the bang olufsen sound makes driving this car a pleasure every single time.