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Used
convertibles
for sale
near
Winthrop Harbor, IL
under $40,000
- Down Payment
- $0
- Net trade-in value
- $0
- Months
- 72
- APR
- 7.0%
- Sales tax
- 0.0%
*Estimated payments are calculated by Cars.com and are for informational purposes only. We’ve estimated your taxes based on your provided ZIP code. These estimates do not include title, registration fees, lien fees, or any other fees that may be imposed by a governmental agency in connection with the sale and financing of the vehicle. Other taxes may apply. They do not represent a financing offer or a guarantee of credit from the seller. Actual terms vary by lender.
**Your Saved Vehicles list will be shared along with your contact information when you submit a vehicle request to a dealership. To opt out of this sharing, please view your options on Cars.com Privacy Notice.
Used
2019 Mercedes-Benz C-Class C 300 4MATIC
Used
2017 Mercedes-Benz C-Class C 300 4MATIC
Used
2007 Ford Mustang GT Premium
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Reviews
Highly recommended and really nice to work with 10/10
Highly recommended and really nice to work with 10/10 great cars Joe and Dani are the best
Mustang convertible GT California special edition
Mustang convertible GT California special edition mechanical work a little bit needed but that’s OK at 130,000 miles. A dream come true my second convertible.
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I had another great experience over at Wickstrom!
I had another great experience over at Wickstrom! This is the second F-150 I've gotten from Michael Kajdanowski and both times have been quick and easy! If you're looking for a new vehicle, I highly recommend you reach out to him!
Great car. Long-term keeper.
I always love BMWs. This is my favorite and most reliable. It's a 2012 with 90k miles and is experiencing only "older car" issues. Love the ease of the top and the size is perfect for me. Warning: be careful of servicing at dealerships. My top was stuck up. Dealership told me $3500 to fix. My regular mechanic told me it was only a little plastic piece and replaced for $0. Dealership: Fermin BMW in Palm Harbor, FL. Avoid them.
Used
2024 Mazda MX-5 Miata RF Grand Touring
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Really Great people to work with.
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.
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.
Used
2003 Honda S2000 Base
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Steve was an excellent sales rep.
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.
Fast and Furious worthy
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.
Used
2016 BMW 650 xDrive
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Rosen Hyundai of Kenosha.
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.
Great Car For Those Who Appreciate It!
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.
Used
2003 Ford Thunderbird Base
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Visited Raymond Chevrolet on 10/10/25 after texting with
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!
2005 Ford Thunderbird 50th Anniversary
I absolutely love this car. My only wish is that I can find a Hard Top to put on it at a reasonable price. But I still love this car. I am sorry but I do. It puts a smile on my face. And I didn't have to pay a fortune for it either. It still looks like new, and it drives great, and it handles excellent. It is the Torch Red w/Black Ink Interior. And this is to the guy that says the 3.9 engine is underpowered, you are nuts, this thing screams down the highway, not that I am a speed demon, but it does. I don't know what else to say about this Thunderbird, but I wish I had bought one many years ago. Nuff said.
Used
2003 Porsche 911 Carrera 4
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I had a Wonderful experience purchasing my vehicle here!
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!
Amazing performance car
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!!
Used
2007 Lexus SC 430 Base
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Neverending Style Dependable best friend of mine ♥
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
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The only car I've owned for 12 years!
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.
Used
2011 Audi A5 Premium Plus
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AUDI A5 Quattro Cabriolet Convertible - Excellent
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.
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Family has owned 3 TT's so far!
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.
Used
2005 Lexus SC 430 Base
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Andy was very attentive, patient, and not pushy at all.
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 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..
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Every step was very organized, and the sales
Every step was very organized, and the sales representative was extremely helpful. Overall, it was a great experience.
I have one, and like it very much; up to a point.
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.
Used
2024 Ford Mustang EcoBoost
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Great service
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.
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.
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I bought a used 2005 chrysler pt cruiser a few years ago.
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!
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I purchased a car from Citi Auto and I couldn't be
I purchased a car from Citi Auto and I couldn't be happier with my experience. Mr. Erdem and Mr. Yusuf were incredibly helpful, professional, and honest throughout the entire process. They made everything smooth and stress-free, answering all my questions and ensuring I got the best deal possible. The car is in excellent condition, and I truly appreciate their outstanding customer service. I highly recommend Auto Citi to anyone looking for a reliable vehicle and a trustworthy dealership. Thank you, Mr. Erdem and Mr. Yusuf!, Thank you Citi Auto!
2001 BMW solid used car if you can make your own
2001 BMW solid used car if you can make your own repairs. 2nd owner bought used form dealer Bellflower Ca. Good looking car. Solid. Thanks
Used
2001 Chevrolet Camaro
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Best car buying experience
Bought a used Certified Mazda best sales experience Robert and Maciek were true professionals knowledgeable and quick recommend to anybody looking for a used Mazda
Just bought the car.
Just bought the car. 2001 Camaro SS in dark metallic navy blue. Honestly the nicest color combo I have ever seen on this car. Stunning to say the least. Tan leather interior. Just turned 50k miles and mint isn't even good enough. Literally showroom quality in and out. Hands down the nicest one I've had and this will be about my tenth F body from 89 to 01 all nice cars. My last one was a 98 Z28 mostly original except the exhaust and a few bells and whistles but nothing over the top. Just had the rear carrier and axle bearings and seals done. 182k and ran like the day it had 60k on it. If you don't beat it and keep up with the oil and other very important and often overlooked maintainance they will go until you crash and total it. That LS1 will just not die unless you kill it will neglegence or stupidity. Best platform GM ever built in my opinion. Could not be happier. Umi 1.5 drop springs with koni shocks and a tik performance m/c for the clutch. C5 ZO6 rims and tires just turned 500 miles. Perfect stance just perfect. 18's in the rear and 17's up front with toyo 888"s. That's about it for mods. Got a few more things I'd like to do come the spring time. There you have it. The nicest Camaro SS out there. I'm sure there are some beauty's out there but better I can't imagine its possible
Used
2017 Buick Cascada Premium
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Best dealership
Great place to buy a vehicle from, made me and my family feel very welcome and made the whole car buying process experience so much more easier than any other car dealership I have been to. I would definitely recommend purchasing a car here, great and honest people here doing what they can for the people
My baby name is Sunshine.
My baby name is Sunshine. The color I was showed was not the color I got. I love blue when I saw the blue it was different, It didn't pop, I was still like ok whatever, as long as it's blue, she'll grow on me. Before I get her I had only seen one a few yrs back and was puzzled like a buick with a rag top?? Is that a convertible?? Anyway, fast forward... usually when u buy a car u start seeing a lot of them. Well, I didn't so I'm looking at cars (waiting on the delivery of mines) I finally seen the blue I was getting and I was like, ok that's cute. The day of my new arrival. Omg she was more beautiful in person and the Blue was NOT the blue I thought. She popped!!! This baby is beautiful and rides so smooth I wanted something different and she has not disappointed me at all she had 15,910mi I've had her for a lil over 6mos. She sitting at 25k now. Absolutely no regrets i am her third and prayfully her last owner.
Used
2015 Mercedes-Benz SL-Class SL400
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Mr Nicholas Woods was very informative and polite.
Mr Nicholas Woods was very informative and polite. Robert Woods explained everything I needed to know about finance.
Last Of The Real Mercedes
By far the best Mercedes I have ever owned. I might say the last of the real Mercedes. 2015 SL400 may be the last real Mercedes.
Used
2025 MINI Convertible Cooper S
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Good staff and easy to enquire and buy car from this
Good staff and easy to enquire and buy car from this dealer Good staff and easy to enquire and buy car from this dealer Good staff and easy to enquire and buy car from this dealer
*Estimated payments are calculated by Cars.com and are for informational purposes only. We’ve estimated your taxes based on your provided ZIP code. These estimates do not include title, registration fees, lien fees, or any other fees that may be imposed by a governmental agency in connection with the sale and financing of the vehicle. Other taxes may apply. They do not represent a financing offer or a guarantee of credit from the seller. Actual terms vary by lender.
**Your Saved Vehicles list will be shared along with your contact information when you submit a vehicle request to a dealership. To opt out of this sharing, please view your options on Cars.com Privacy Notice.
Find great prices by city
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Convertibles under $40,000 in Winthrop Harbor, IL
56 Great Deals out of 193 listings starting at $2,499
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48 Great Deals out of 164 listings starting at $2,499
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62 Great Deals out of 230 listings starting at $2,499
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30 Great Deals out of 103 listings starting at $2,499
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76 Great Deals out of 283 listings starting at $2,499
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81 Great Deals out of 301 listings starting at $2,499
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78 Great Deals out of 284 listings starting at $2,499
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78 Great Deals out of 273 listings starting at $2,499
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41 Great Deals out of 145 listings starting at $2,499
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72 Great Deals out of 251 listings starting at $2,499
Find great prices on used Convertibles in Winthrop Harbor, IL
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