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

Amazing Dealer amazing staff great prices. Amazing financing as well. Nick and Rudy took care of me from the first call

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 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.

I love this car. So many mods can be done to make it your own and unique to you. Move currently produces more hp than a stock GT 350. The looks and performance are outstanding for a car in this price range. My only gripes are that occasionally one of the mirrors (actually happens on both sides just not at the same time) will go all the way in one direction until it can't go anymore then click constantly until you press that mirror and touch the manual adjust button. Then you can hit your pre set of you have one and everything will be fine. It's always when I unlock the car to get in that this happens and it's totally random. If course the dealer can never find anything wrong with it. My other gripe was that on occasion it wouldn't recognize my fob. The only way I could start the car was to lift up the cup holder mat and stick the fob in the slot. But then if I went somewhere and turned the car off, it would be fine. Again totally weird and random. Overall though, I wouldn't give this car up for anything. So much fun to drive, and the sound of that V8 exhaust just gets the blood flowing. Not to mention the all the looks you'll get from people.

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.

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!

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.

After a negligent driver rear-ended my other car, I bought a 2022 Mustang GT Premium with the insurance money. I had a 1979 Mustang Cobra years ago and loved it. This is a great car, too. Fast, comfortable and beautiful. I haven't driven it in snow yet and have some trepidation about that but otherwise I'm glad I bought it. There are only three things I don't like: the car payment (who does?), the gas mileage, although I can get 30 mpg if I drive 58 mph, and there seems to be some high school kid at every stoplight who wants to race. This is definitely a car worth buying if you're an empty-nester, going through your mid-life crisis or single and don't have to haul much in your trunk.

Very responsive, kept me up to date and availability of the car I was interested in.

The redline Sky is an amazing car for the money. So much fun to drive...the power and handling on this car are better than cars twice as expensive. Super reliable 2.0 4 cylinder turbo makes it a worry-free convertible. Love it!

Worked with John B for a new Bentley. He was quick and efficient, answered all my questions and the car is in mint condition. Car was fully serviced and I love it

Update from Vette Guy of Tucson, Az. I received my replacement Z-06 convertible almost exactly 2 months from the date I ordered it. It arrived exactly as ordered: Mist Red with Natural interior, Z07 Handling Package, Visible Carbon Fiber Big Aero Package, Carbon Fiber Wheels and Racing Seats. I have 800 miles on the car, so far no problems. I plan on racing the car in the September Silver State Challenge Ely, Nv. open road race. I raced the 2023 Z06 there in May, great race try it! I'm also attending the Z06 driving school in Pahrump,Nv. I did the Z51 school last year, highly recommended! Overall a big Thumbs up to Watson Chevrolet for keeping their word on getting me a replacement Z-06!

Professional and friendly staff. Clean and inviting facility. Sales team are responsive and work hard earn your business.

Porsche was my dream car and have owned the 2007 911 Carrera S for many years. It is everything I desired in a car. Smooth, fast, reliable and beautiful Black with Black interior and manual shift. I have owned two Corvettes, an MGB and Pontiac GTO, but the Porsche 911 is a keeper.

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.

Great to go to local car events.Fun to drive,always turns heads.Driving with the roof off is exciting on a beautiful day.

I had a problem with my 2025 Honda HR-V. Scheduled an appointment and Tim helped me when I arrived. Tim had the tech go through the car after I explained what I was feeling, and when they were done, they recommended a plan to resolve my concern. Tim was especially helpful and I can highly recommend him for any of your service needs. He’s very knowledgeable, and easy to talk to. He listens very well!

I’ve owned a Sahara unlimited for 2 years then purchased a 2019 sport unlimited, hands down the two best cars I ever drove, they don’t exceed in any one category besides getting you where you need to be in style!! I’ve loved every minute of my jeep wrangler!!

Best experience I've had when purchasing a vehicle. Everything was handled quicky and professionally with no pressure to consider anything other than what I had asked for. I was completely satisfied and would recommend this dealer and my sales associate Larry.

I have the 430i G22 (coupe), sports package,shadowline trim,. It is my daily driver, looks amazing and handles phenomenal. I get comments everyday by random people saying the car looks amazing. I have the Brooklyn Gray with the red interior which I believe is the best color combo.

Fast and easy. All staff was pleasant, well spoken and mannered. Made an out of state purchase with a few email and phone calls. Sales person Luke was excellent.

It is amazing the difference 5 years can make. Traded a 2014 BMW 640i xDrive in for a 2019 BMW M850i xDrive. It is a beast! Handles great, very solid and I like the extra hp and features.

buena atención Joel Hernández muy amable y calidad en servicio y rapidez en su trabajo

Absolutely the best mix of performance, luxury, and technology in an all wheel drive package that is unmatched at this price point. Comfortable for long cruises and sporty when you want. Punches way above it's class.

Ryan Paul was outstanding! Smooth purchase buying a Q3! He was so personable and made my experience wonderful. He’s funny too. He knew all the answers to my questions as well. If you are in search of a car, ask for him! He made it a truly great experience for me. Thanks! Sid was great too. and shout out Robert:)

It’s currently summer 2025, I’ve owned my 2020 Wrangler Sahara since spring 2021. I LOVE my jeep and have had ZERO issues with it. This is my 2 nd Wrangler, first one was 2915 New. No issues with it at either. Mine is a 4 cl turbo. I didn’t want that I wanted a 6 cl. My husband convinced me to buy it and I’m glad I did. I have 59,000. Miles currently and I haven’t had to replace anything besides general maintenance.

An amazing experience! Once arrived I was greeted and given a beverage of choice. Then since a majority of technical information was completed via online portals, was able to sit down and do “paperwork” for less than an hour. For one this made the part I dread the absolute most, an absolute breeze. In addition, I absolutely loved how there wasn’t any pressure to make the purchase or not. It was as if I was buying a car from family! I highly recommend this dealership and will be going here moving forward for future cars!

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...

Service department was prompt, very thorough and kept me informed as progress was made. Their work was efficient and thorough. I have been using Tasca and previous owners for many years and will continue to use them.

2023 Chevrolet Camaro ZL1 Convertible It doesn't get any better than this in a Camaro. Absolute cream of the crop car. ZL1 comes with évery creature comfort you'll ever desire other then it driving itself & that would take all the fun away. Complete comfort, endless source of power & everything that brings happiness to your eyes 👀. I paid $80000.⁰⁰ & have zero regrets, best & happiest investment I made, cause I'll have this for the next twenty plus years.

Bill Baroud was very easy to work with. Straight forward, no ?sales? pressure The staff was very friendly and helpful. I am not very sure what else there is to say

A 1995 Chevrolet Camaro Z/28 convertible is always an attractive idea. its a loaded, low mileage V8 droptop for such an affordable price, you'll realize this slick red machine is irresistible. Believe it or not, but the '95 Camaro has passed the quarter-century mark. That means it's eligible for classic car insurance and vintage car plates in many states. So, this is truly a modern classic. And because this Camaro has averaged less than 4,600 miles annually, it doesn't have the look of a daily commuter. The sharply pointed nose, sleek rounded side panel, and well-integrated rear spoiler are an awesome package, especially when finished in a vibrant red. The black convertible top looks nice against the black accents around the body. The Z28 emblems are original against the Emerald Green allowing the secrets of sole and contents. The whole car has the look of a well-respected machine, right down to the factory 16-inch alloys. In fact, the only addition we can recognize are the bright exhaust tips out back, and they just remind everyone why we love a good Z/28.

We had an outstanding experience with Alex Lopez while choosing our new Lincoln Nautilus. From the very beginning, he was professional, friendly, and incredibly patient. He took the time to explain every detail, answer all our questions, and guide us step-by-step until we found the perfect vehicle. Alex made the entire process easy, transparent, and pressure-free, which we truly appreciated. His knowledge of the vehicles and his genuine interest in his customers really stand out. We are extremely happy with our new purchase and highly recommend Alex to anyone looking for top-quality service. Thank you for everything, Alex! 🙌🚗✨

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!

My experience w/Highland Park Lincoln has been quite satisfactory....expecially the Service Department. But, it is a thirty seven mile drive to get there.

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).

I has a Great buying experience at Porcaro Ford! I was looking for a newer mid-sized SUV and the salesman at Porcaro listened to my needs, showed me what they had and offered to search for a vehicle if needed. Luckily the 2019 Ford Edge ST on the lot was a perfect match. Very pleased with the whole experience.

A beautiful automobile gift from my beautiful wife on 6/2/23. I’ve been searching for a tbird and a friend told me to call and see if this guy was willing to sell one of 3 Tbirds he had. Little did I know in a few hours I’d be the new owner of Dale Jarrett’s personal Tbird with only 6,842 miles on it. His signature is on the dash and also his personal leather racing jacket signed. Needless to say it handles like new and has new car smell. We drove it from Charlotte NC to Charleston SC and couldn’t believe how it performed handled and rode. It’s definitely an eye catcher. The hardtop was easy to remove with 2 people. It would have been nice if it would have been designed to retract into the trunk. But mine came with hoist to attach to garage ceiling which made it very easy. I’m 100% satisfied and happy with my new Tbird.

Their level of customer service, communication and follow up was very good. They strive for customer satisfaction and work to place you in the right car.

Great GT. Very comfortable. Excellent performance. Super good looking. Would buy again. Is the 3rd SL we've owned and, is likely, THE best one of all. Doesn't have that V8 sound but at $20K less in price, we'll accept that . . . in a heartbeat! I.e. 0-60 in 4.5 seconds and 107 MPH in the standing 1/4 mile is plenty quick enough!