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

Great customer service and Bob was helpful but not pushy at all during the process. Great experience that was worth the lengthy drive. I would recommend!

The previously leased and Audi certified TT was the only logical choice for my wife and me when our old 1999 Audi A6 suddenly became unreliable and too expensive to maintain. Three years old with a two-year extended warranty, the 2016 TT is a powerful, agile yet economical alternative to the A6, and its quickness makes interstate driving a delight. It's simply an amazing machine. We've never had a vehicle as classy and attractive as is this one. Hats off to Mamta and her cohort at Chantilly Audi.

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

Have owned many premium cars. This 640 is our first BMW. This vehicle is attractive, fun to drive, and well equipped. The buying experience was exceptional. Definitely would buy again.

My daughter went to buy a car here with Chase and I’m glad to say that I had not to worry about her coming back with a bad deal! He ensured that she finds the car she wants. Thankful for Chase guidance and patience in the process to ensure that I was also satisfied and gave the go on everything. Good job my guy!

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.

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.

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 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 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.

I was initially looking for a used Golf, but the more I looked at the Beetle the more I liked it. When I found the one I ended up buying, it was love at first drive. This little car packs a punch with the 2.0T, and will throw you back in your seat. It’s an absolute blast to drive. Handles well around town and on the interstate, where it could easily get one in trouble since it wants to GO. The same engine as is found in the GTI, so this should be unsurprising. Easily gets 30+mpg on the highway when cruising along, typically around 20-25 city. These cars handle city driving just fine, but they are meant for the freeway in my opinion. I find the interior to be quite luxurious. Heated leather seats (not available in the Golf) with plenty of storage compartments. Not many frills, just a sleek and mostly practical dash. The trunk is big enough for grocery runs, and the rear seats fold forward for larger loads. It’s not going to haul large appliances or furniture, although it could possibly carry some bigger stuff on a roof rack. The Fender audio system is impressive, wouldn’t change a thing about it except it could benefit from an updated head unit with CarPlay. This hasn’t been an issue for me. I think the car is a real looker, it turns heads and has drawn the occasional compliment. My used model had some imperfections, but it’s still a great looking car that I want to look after and keep for as long as I can. It feels well built, the doors close with the satisfying weighty thud of a premium vehicle. Overall, I am very happy with my 2013 beetle. It’s not only fun, but it seems to be reliable with a couple caveats that some owners might not be aware of. The 2.0T engine is designed for premium fuel, using regular will eventually damage it. The 2.5 can run regular, but I believe the 1.8T will also want premium. The reason for this is lower octane fuel will cause detonation in these high compression engines. If you don’t know what detonation is, just know it’s bad. The oil needs changed more regularly than the manufacturer recommended 10k miles. 5k to be safe, 7k at a stretch. This is especially true for higher mileage vehicles. Speaking of stretch, there is a known issue with some 2.0T engines where the timing chain stretches over time and many miles, so if buying used that’s something I’d have a mechanic check out. This is an expensive maintenance item, but IF it’s needed, getting it done along with the tensioner and a new water pump for good measure will ensure that the new to you Beetle is reliable for many years and miles to come. The other issue is carbon build up. Getting it cleaned out is not as spendy as the timing chain but it’s also not a cheap fix. I believe this can largely be avoided by using top tier fuel (it contains detergents that help with this) as well as regular oil changes and some regular spirited driving. Would not recommend this car to someone who mainly does town or city driving, the 2.5 engine might be better suited for that. According to my research, the 2.5 is quite bulletproof BUT it’s not good for any engine to be driven at low RPM all the time.

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.

Andrew Doyle at this dealership was amazing to work with. He was soft spoken, detailed yet concise. He was influential in making a deposit for a purchase. I had to pull out later for other reasons. But I give high regards to Andrew’s work.

Solid for a convertible. Goes surprisingly well in the snow and with the seats down can haul stuff. I have this as my only car and it is actually very practical. Plus, it’s just a joy to drive.

Every one I met here were extremely nice and very welcoming, they answered every question I had and I would definitely recommend this place for vehicle shopping.

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!

5 stars was a good place and answered all the questions that I had about the car

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.

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.

I had a great experience at Frey Automotive! I live near Naperville, IL and have A LOT of dealers to choose from. I was looking for a used Nissan Leaf with Quick Charge, and all of the dealers near me had a lack of knowledge about this car even though they were trying to sell them. I called several dealers near me to ask about their Nissan Leaf inventory. Most of the dealers didn't know what quick charge was, the photos they posted didn't help verify if the car had it or not, and some of the dealers started sending me emails saying "free oil changes for life" (Nissan Leaf doesn't use oil...). Finally, I came upon Frey Automotive's website and found the car that I ended up purchasing. The car's description and photos made it extremely easy to see that this car was an exact match! I drove up to the dealership to meet JJ for a test drive and to talk about the car. I've only purchased 2 other vehicles in my life, but this was the most hassle free purchase I've made. We both were able to agree to an honest price for the car (and the price was on the low end of market value, which made the deal extra good for me knowing I didn't get ripped off). I came back for the car the next weekend once finances were in place and the car has been perfect ever since!

Love driving this fun car. Maintenance has been an issue and will probably only get worse... Item: Like most modern cars, there are no grease points in the suspension. So when the little rubber boots that cover the joints rot away, there's no way to lubricate the suspension, and the parts start to grind against each other. Out $4k to replace the front and rear suspension. Had them do the struts too since they had to take everything else out. Item: Many parts no longer available. The accelerator pedal switches failed. No Ford or aftermarket replacement to be found. Good news: found one at a salvage yard. Bad news: it's the same age as the one it replaced. Item: Crack in the windshield? Stay away from any chain that rhymes with "Chafe-Bite." Replacing the windshield means removing the frame. Very few of their techs are trained on how to do this.

Great family friendly 4 seater hard top convertible. Good performance and great handling as well. Purchasing used was a great value for all the included features.

I bought my 2003 mb SL500 in 2023 with 30,000 original miles. It runs excellent has a bullet proof engine and design will always be IN vogue cuz of its sleek design. I got all the previous repair receipts from original owner which is great to know the history. As with any 21 yr old car there may be repairs. I have a great MB independent repair shop called Star Motors in Gainesville Fl who really knows these cars and they fix them right and for less than a dealer. Sure thing’s can go wrong and I have found repairs about 25% more than Honda or Toyota. One has to factor in repairs no matter what. I like the 5.0 engine and one thing is they last! They ride so smooth on the wide tires on the highways and there tight steering. Bose sound system still working great afte all these years. Buy one have it inspected if your worried. There in my view great cars. Depreciated a lot since new at $100,000 out the door. So paying 15k to 20k is a bargain. You’ll love it!

Simply Outstanding!!!.. What a fantastic experience!!!.. Professional.. helpful.. knowledgeable..the Owner Tom really ensured he spent quality time with you to fully answer any questions you had.. he really knew his business and was there to help his Customers 🙏

Its weird to read bad reviews on this car, specifically the sl55. Im on my third one. All used. My latest purchase was October 2019. a 2004 sl55. daily driver. I am second owner. Top up and down every day. 95 south Miami traffic and heat. She's been perfect. You just need to find one that the service was kept . The suspension is only a problem when neglected. and now with all the parts and certified techs (private) its a $4,000 fix. Or , do like some others and go coil over for under a grand. I would get in mine and drive anywhere with out any hesitation.

Max and Sam were very helpful and accommodating. Answered all my questions and provided information. I did a test drive and liked very much but eventually thought the vehicle might be a little bigger than I want or able to fit in my garage. I would definitely recommend Little House Of Cars.

This is my dream car . It is fun and sexy and built for curves . The top tucks into the trunk with the touch of a finger ,so you can drop the top at a red light .

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.

So far so good...Mitch at the Dealership has responded to questions right away...no problems there. Here in Cleveland area we had two tornados within a couple miles of me Tueday...no power since and busy cleaning up trees. Hope to continue with Dealership when I catch a break.

This is my second Volvo C70, the last one I bought is the T5 Polestar Engineered with only 35.000 miles on the counter. The first C70 I swapped with my Mustang convertible. This is the best car I have ever driven! Every time we go to France the holiday starts with the beginning of the journey! It drives smooth, not the fastest car but just enough and it cruises likes it's made for it!

Very good candidate for easy total restoration. One 6 inch rust spot, several small surface rust spots. Drives great. Gets smile and thumbs up on road.

I purchased a used car here at a very reasonable price. Shortly after arriving in the U.S., they were very polite to me even my English communication skill is not so good. They were so quick to maintain my car!! I've had many bad experiences at other car dealer in the US but not with Albo Auto Sales! I am grateful to have been able to purchase a car from Leo here and to have met him. Thank you so much!

Always a dream Mercedes Benz! Fantastic car to drive and enjoy Life! Drives like a dream! I do Bilsteins B4 and H&R springs with 18” Stagger Wheels! A Super Car!