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

Great experience. They bring cars to like new condition before selling. Would return as a customer.

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 have two Jaguars. The first a 2001 XK8, I bought in 2015 from the original owner. The 2nd, a 2007 XK, I bought after the original owner traded it in to a dealer in Oregon. I had it shipped to me in Alabama. Both are a similar Pacific Blue, the 07 being Indigo Blue, slightly darker. The 01 has Ivory interior, the 07 has beige. The 01 has quite a bit of recurring maintenance from a host of items that needed redesigning, which was accomplished on the 07. Everything needed was done. The big differences between the two cars is trunk space and cabin space. The 07 Cabin accommodates a taller person where the trunk on the 01 would hold a VW Beetle and easily close. I redesigned the 01 upper shock mounts and rebuilt the mounts with new polyurethane bushings that should outlast me. I have replaced them with OEM 3 times since 2015. That chirping sound you hear is the shock mounts, metal to metal chirping. Anyway, the 01 XK8 is a nice automobile that needs near constant attention. The 07 XK is a Super Luxury GT sports car that is easy to maintain and so far, bulletproof. Nothing that I have driven in it's class compares equally. Everything else has a harsher ride and are regular sports cars. I have owned Corvettes, BMW's, Acura's, Mercedes and Porsche's. None compare. So far, I've had people compliment me on my Miata (the 01) and Corvette (both the 01 & the 07)... Jaguar is a brand of only a few in my location... very rare and no one knows what it is... up close, they just can't read, I guess. The guy was staring at the Jaguar emblem when he called it the best looking Miata he had ever seen. LOL!

Great experience with John and Florin. They know their stuff which made this transaction stress free.

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!!

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

What a great car to drive. I beat on this 2ss constantly with absolutely no problems ever. As far as Evelyn and the blend door, you never have door issues if you don't drop pens or mascara and stuff down from the dash and jam it up. I haven't had one problem in 100,000 very very hard miles and 4 or 5 sets of tires. Overall an amazing fun car

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.

it was just some presales questions and they were quick to reply and offered a lot of assistance.

Recently purchased a 2024 4 series convertible. Love the way it looks and drives. ‘Ordered the car with the assumption that it had the cruise control and lane as dust that I was used to in my other vehicles. This car does not come standard with a front facing camera. Also does not come standard with the cruise that is what I call “radar” cruise. Just putting it out there for anyone shopping. I do love the car.

The dealership contacted me and followed through on everything I asked and needed of them. Great overall experience.

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.

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...

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

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!

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

Went from a Sahara Jeep Wrangler to this beauty & i Don’t regret it one bit. Amazing interior & exterior quality. Very clean & comfortable. I love it.

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.

Great comfort and every conceivable feature. Responsive steering and breaking and plenty of power. Doesn’t hurt that it a beautiful car in perfect condition. Bought it at the right time from the right place.

Was in and out under 30 minutes. Small family dealerhsip, they kept thing simple. You can spend an entire day in a big store, cant deal with all that.

I spend about $1000-$2000 each year on maintenance. One may consider that high, but I purchased a 911 C4S car for $35,000; the MSRP was $93,000 in 2004. The vehicle has appreciated since 2019, and now, with such a detailed service history over the years, it could sell for $40,000. So you either pay in depreciation or maintenance, and though I may be a stickler for maintenance, it keeps the value stable. I could have gotten a new Camry for $35,000, but it would be worth about $15,000 now and less fun. Next car I will jump up to a 2012 to 2015 Porsche. You can't go wrong if you get the right model, rare options, and even rare colors. Number one is having complete maintenance records; don't buy one without them.

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.

I bought a 07 CLK 63 AMG about a year and a half ago and never had so much fun in a car since a 62 Shelby Cobra! The CLK is very well appointed and it looks a bit of a sleeper but it does not when you wick it up. I have a Dragy and use it to do 0-60, 1/4 mile and Speed mile. I am getting better at driving this car as times will show. If you are looking for one of these you will have your work cut out. I took me 6 mon. and nation wide search. I found a perfect one with 22K. Love it.

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.

These cars are an amazing value. Quite simply many people hate the styling. Hence a low price. Nothing I write matters on this. You like it or don’t or put up with it for the value. The interior is simply stunning. Other than a Bentley I had no other car I’ve seen is nicer inside. Quality materials. Nice leather. Stunning real wood. And unlike anything else a way to cover the nav screen with a wood door. Stereo is excellent. Ride quality is fantastic for long trips. No. Not a super fast car in corners. Fast enough and very comfortable. Engine is silky smooth and whisper quiet. Except when you floor it you get that v8 growl. Again not a dragster but plenty powerful enough. The roof is magic. A hardtop coupe most of the time but a fantastic open top with minimal buffeting. Reliable. Very reliable. Excellent Lexus service if needed. Our 2004 has merely 60k miles and zero repairs. Many of these are low miles. Toyota reliability is a great comfort. Big and heavy and safe. Plenty of airbags and great brakes. Mass is safer than lighter cars. Do the negative? It is not easy on gas. Styling is either love or hate. Navigation system cannot be updated and CarPlay is not available although there are kits to add it including nav music and phone. So the electronic toys are dated. To give you an idea my new car is a Porsche 911. Modern. But on long trips or just getting from A to Z the Lexus is first choice. Porsche is more modern and exciting but … not as beautiful inside nor comfortable. I totally recommend this if the styling and gas mileage and electronics are not an issue. The value is unbelievable and unbeatable.

Mr Nicholas Woods was very informative and polite. Robert Woods explained everything I needed to know about finance.

Best and most fun car I have ever owned. I bought it in 2008 with only 11,000 miles, so only drive about 11,000/year for the past 13 years.

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.

My dream car. I patiently waited until I could afford it. Purchased a pre-owned, one owner, 2017 S63 with only 17k miles for nearly half of original MSRP.. I can't be any happier...

Autos of Chicago prides itself on offering a dependable selection of used vehicles with quality you can trust. From fuel-efficient sedans to family SUVs and performance cars, each vehicle is carefully evaluated to ensure value and durability. With fair pricing and knowledgeable staff, customers enjoy a smooth buying journey from start to finish.

Never a "have to have it" kind of car guy until I saw, researched and drove this car. It's a solid, powerful, and super slick cabriolet that only catches the eye of the passionate. It has a beautiful saddle leather interior with gorgeous wood details and a really good stereo that rivals todays' car stereos. It has strong and silent 4.3 V8 that is top of the list reliable. I bought my 2002 in 2023 and fixed a few things with the audio system and is now a low-mile like-new car. I love driving it when I can and will til I can't drive anymore.

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.

This is the forth Viper roadster I've owned ('1994, 2000, 2003, 2005) and no complaints about any of them. I love the "wow" comments I get when people see the Viper. Corvettes, although great cars also, are a common site everywhere you go. Not true with the Viper. I also love the rear wide track and bodacious rear tires. There may be more comfortable and higher H.P. sports cars, but none as good looking, worry free, cheaper to maintain/repair or fun to drive. I believe the Viper gives you the most bang for your buck.

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.

I purchased and held car for 4 years. After I purchased the car it needed many things, water pump failed, brake lines, alternator failed, motor mounts failed, cup holders snapped in all I spent about $15,000.00 on it in 4 years on a well cared for car with about 40k miles on it. It’s not cheap to keep up and I did not overpay for repairs at the dealer. It’s a great car however it’s going to cost you to keep it up properly. All the while you own it you will have fun when it’s not in the shop. Every time you hear a noise you wonder what is next and how much will it cost. This is a car for owners with disposable income, time, an extra car and a good local Porsche specialist.

Tony & Cam were beyond a five stars, they made the process extremely fast & easy. The whole staff made me feel very comfortable and confident about buying a Maserati. Definitely would come back again. Thanks again ENE!

Had this car for about 2 years but need a car that is going to be better in the snow. Have had no complaints what so ever about it. Drives great and sounds amazing as well.