Used convertibles for sale near Winthrop Harbor, IL under $100,000

I’m really impressed with the service at Autos of Chicago. The staff was knowledgeable, friendly, and took the time to understand what I needed. They walked me through each step and made sure I felt confident with my decision. My used car runs perfectly. I would definitely return and recommend this dealership to anyone.

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.

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!

Love it! Powerful engine, cute appearance, hard convertible top. Back seat is small but it’s still nice to have the option of fitting more passengers. Very limited trunk space. Perfect for summer days and is very well-made and designed.

Steve was an excellent sales rep. Ultimo has a great stable of cars to select from. Steve went out of his way to help me with my trade in, new summer wheels & tires and answered all of my questions accurately.

This car was not in the best shape at first but I changed all that for myself. I updated the things that it needed to extend its life. And now I'm sad to let it go. Only because I have some important things I need to take care of. But, I will get another one for sure in the near future. For now I have to say goodbye to a good well friend.

The Service Department at Glenview Luxury Imports never fails to provide phenomenal Service. Jon, Ketan, and Gary are always helpful in answering questions and coordinating service appointments at the earliest time available.

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.

Really Great people to work with. Mr. Lee McGee did everything he could do to help me with my Purchase. Highly Recommend.

Car drives and handles like a true sports (not race) car. The hardtop convertible is a big plus especially if you aren’t keeping this somewhat protected from the elements. The only small complaint is where the glove box is located. I understand they have it in the center for interior constraints, but I wish they would have found some way to have it by the passenger front side.

Estamos muy satisfechos con este dealership, su equipo es fantastico. Todos los vendedores y jefes son muy amigables y Profesionales. Lo recomendare a todos mis familiares y amigos.

Quick, classy and fun. Makes you feel good every time you start it. There are cars that do many things better, but as a package it cannot be beat.

Nice and all staff are very friendly, and everyone there was so much fun, and Ed Wanland have a great time to work out for me. Thank you

This is my second Mini convertible, my previous one was a 2007... I also own a 2014 Mini Clubman. I just LOVE this car!! Super fun to drive and "dress up" with little customizations. I have the "S" model in an automatic now and, unfortunately, it's not as good on gas as my '07 manual was, but hey, it's a small price to pay for so much fun!

Rosen Hyundai of Kenosha Has a great service department. They do a great job. They’re very honest. Cherry is outstanding. She works in the service department. Very honest. They don’t sell you things you don’t need lot of dealers will tell you you need parts you don’t need. I highly recommend Rosen Hyundai of Kenosha to anyone they won’t be sorry. I live in the northern suburbs in Illinois and this where I go to get my car serviced. I’m very happy.

I wanted a year around convertible grand tourer with a back seat and a useable trunk that was fun and comfortable to drive. I looked for six months and having given up on other brands I finally turned to BMW. The 650xi always puts a smile on my face especially with the top down. Depending on your previous vehicle it may take some getting used to, however. It is "low rider" and while there are more seat controls than a pilots control panel, you may not find the right seating arrangement initially. The car is second nature to me now and very comfortable in every way. The more options your 650 has, the more you will continue to find new features continually. I purchased the car used and have had it for 18 months and appreciate it every time I drive it. It's good in the snow and l always feel safe in it. The convertible top is not as insulated from sound as I would like for highway driving but other than that I have no complaints. It is a satisfying vehicle.

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!

When you buy a Porsche 911 you buy it because of its performance. My car now has 96,000 mile are runs and drives as it should. I do several DE track days every year. It has never let me down. It is amazing to drive, steers like it is on rails, stops on a dime, and goes as fast as I need it to go. What a great car!!

Very smooth V8 engine/transmission, faster than most cars, the interior is perfect for me 6ft tall, sound system has some deep bass, I would marry my sc430 and I believe my sc430 would get the "Will" built to last, til deff du us

This car is a great city car, handles well, accelerates awesome, looks great. Great for trips, comfortable, fast, smooth. Great for all weather. xxxxxxthrough a foot of snow, handles ice, and rain with secure confidence. I've never gotten stuck in this car! There's a reason half the cars in Boulder are Audi's. It's been reliable transportation and lovingly cared for.

This is a perfect car for California, especially now in needing to get out to feel free. Nothing is better than driving the coast with the top down. This Quattro is in excellent condition driven by my wife who took great care of the care.

Sporty, fun, zippy. My second TT - my loss, your gain. A safe, well-engineered ride. Must see to appreciate. Detailed and road ready. High quality leather interior, heated seats, great MPG.

Andy was very attentive, patient, and not pushy at all. Thanks Andy for a car buying experience!

I have had a Lexus 430 SC for 8 years I love this car.I had a Mita before,.wanted a heavier car to drive on the interstate.this car is a dream very smooth ride. Easy top Down....had very little problems. It's unique and beautiful....I love the back seat..great for a dog or child or your coat and purse. . The mita had nothing...no it's not for everyone, but I like it....better than any new car....Getting ready for a new timing Belt , which they say will take care of most of the maintenance for long time. It is a 2004. They only made this car 2002 to 2010..

Every step was very organized, and the sales representative was extremely helpful. Overall, it was a great experience.

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.

Sam provided outstanding service. He was always available to take my calls and ensured that the entire purchase process was smooth and stress-free. I truly appreciated his professionalism, responsiveness, and support throughout.

If you are after comfort and looks, this is the car for you, but, and here's the big but, be prepared to spend more than normal for maintenance. It is a Jaguar, and that is a small company, and there are not that many dealers to take the car to, and when you do, bring a full wallet or a very good credit card. Not a sports car. This is a grand touring car, and not something for the race track. It is pretty quick for what it is, and it does handle well.

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

Excellent value for the price. Do not purchase this vehicle without the active exhaust option. The fake vents are disappointing but otherwise the car is perfect.

I purchased a Mercedes SL500 as an anniversary gift for my wife and dealt with both Brian and Tom (the owner) throughout the sale. The car was as described in their ad and they were super easy to work with. My wife loves the car and we've been going back to have them service it and store the hardtop too. We've had a good experience and would recommend them for both sides. If anything just stop in and see the cool cars they have in the showroom and in back too.

Visited Raymond Chevrolet on 10/10/25 after texting with Blake. When I arrived I was greeted immediately by Drew and he seemed to immediately know exactly why I was there. Pulled the car around that I wanted to look at and off we went on a test drive. Drew had more of a consultative approach rather than a high pressure approach which was definitely appreciated. The car drove great, yet my hopes weren’t high due to the fact that I have bad credit because of some stupid mistakes I made when I was young and haven’t spent the time/effort to repair yet. After a quick discussion with Drew upon our arrival back at the dealership, Jerry, the Used Car General Manager, came over to sit with me and he answered every single question I had written down (and there were around 15 of them!). At this point, they already knew my credit situation since I made them aware pretty early on. Instead of just going through the motions, EVERY single employee at Raymond Chevrolet took the time to make sure my questions were answered and ensure I had a great experience and I never felt less than or judged because of my credit situation. After Jerry answered all my questions, I wanted the car! I had previously been denied for an auto loan through a local credit union (even with offering a higher down payment than I did at the dealership). It didn’t take long at all and after a very short wait Jerry came over and approached me with his thumbs up, “we got you approved.” I was literally shocked….Sure, I didn’t get the best interest rate possible, but with my credit, simply getting an approval at all was amazing. At this time it was around 9:30 PM and the dealership closes at 9:00 PM. If there was an employee that was needed to make this happen for me that night, they hung tight and worked late to make sure I was taken care of. I want to give a special shout out to Janelle, the Customer Experience Manager. Janelle walked me through some very important Tesla specific topics and was very patient with me. The entire time I felt like I was being HELPED, not SOLD. Any “add-ons” were throughly explained and literally each one made sense with my situation (kids, first time Tesla owner, Chicago winters, etc.)… They offered me what I really needed, not just what they could make extra money on. Janelle made sure that I was clear on everything and then I wrapped up the process with the Sales Manager Cooper. Cooper made the signing process extremely easy and went above and beyond to make sure that what needed to get done, got done that night regardless of the time or any obstacles we encountered. At this point, I was extremely happy with my experience & it was time to head out at which time Jerry (manager) and Drew (sales person) escorted me from Antioch to Pleasant Prairie just so that I could take the vehicle home THAT NIGHT. Keep in mind, by the time we arrived in Pleasant Prairie, WI, it was at least 1:30 AM. My plan was to check out a vehicle so that I could then go look for a co-signor because I didn’t think I stood a chance of getting an approval; however, the folks at Raymond Chevrolet made it possible for me to make ONE trip to the dealership, purchase the vehicle ai wanted AND take it home that same day… All while going above an beyond to make sure that I was taken care of and having a great experience which I 100% did. IF YOU ARE AFRAID THAT YOUR CREDIT WILL PREVENT YOU FROM BUYING A CAR FROM A DEALERSHIP, I URGE YOU TO VISIT MY NEW FRIENDS AT RAYMOND CHEVROLET AND JUST GIVE THEM A CHANCE TO DO WHAT MANY PLACES JUST AREN’T ABLE TO - ON MANY DIFFERENT LEVELS (non-judgement environment, friendly and extremely helpful staff and even the ability to obtain an approval for financing for someone with POOR credit). Every aspect of the experience was on point and I highly recommend visiting Raymond Chevrolet if you’re in the market for a new vehicle and you want to avoid the high pressure sales tactics that we see too often at dealerships! Thanks for everything, guys!

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.

I bought a used 2005 chrysler pt cruiser a few years ago. My wife found in in Trenton , NJ. It was a one owner with just over 30,000 miles on it. We only drove it a few blocks, tried the convertible top and was sold on it. I had a small accident a few years ago but it was fixed fantastic like new. I love my car everything works like new and always getting some compliants Inferno Red Black Top Will never sell it!