Used Mercedes-Benz SL-Class for sale near Chicago, IL under $99,977

Just bought my dream car recently from Pete. He is such an excellent guy to deal with. Honest!!! Business minded !!!!! He doesn’t just promise. He deliverers ! Action speaks louder than words. Thank you very much for your help. Makes our buying experience a lot easier than I expected.

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.

Great experience. I've been looking for an X5 with a particular set of options and finally found one at iCars' showroom. From first contact to the car arriving was exactly one week and the process was so easy that I've joked that it felt like I was doordashing a car. The car itself is perfect; exactly as described. For having 55,000 miles it looks, feels, and even smells like a new car. I couldn't be happier. Thank you Jasin!

One of the better Mercedes models to have ! All together very nice car ,have everyting you need from confort to speed No need for faster one

Even though I didn't purchase the vehicle I initially was interested in, the entire encounter with this dealership was impeccable. The owner and his salesman were helpful, patient and respectful. As an individual with autobody and mechanical knowledge, I highly recommend this dealer.

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.

Recently purchased a barely used 2025 Honda from City Werks. Their price for the vehicle I wamted at the time was one of the lowest in the country. Steve A was my contact there and made the sale as painless and as easy as possible. They honored their price and didn't xxxxxx around. It was a relief to buy a car that was what I wanted but wasn't hassled and had to play the dealership game.

I had a 2013 was total loss after a pickup truck ran into me on my driver door! walked out with no problem! Very safe car. im living proof. Now i replaced it with a 2014 sl550 Im A happy man!!!!!

Finding a reliable, well cared for, low mileage and reasonably priced used car can be a daunting task. It does not have to be... I bumped into Oswego Motors quite by accident. Spoke to Chad on New Years Eve having seen a car on the website that seemed suitable. I drove out to the dealership that afternoon, and found the car inside and cleaned up ready for me to view. Chad walked me around the car and we discussed not only the condition of the car, but also what I was looking for generally in a used vehicle. I was handed the keys for a test drive, and was told to take my time and drive it as much as needed to check everything out...which I did. We briefly discussed the price. I told Him I'd think about it and call after New Years Day. No pressure, none...to close a deal then and there. I returned on 1/02/23 and not only bought that car, but ended up trading in my 2018 BMW for what I consider a very fair price. The trade-in, was a bit of a spur of the moment decision on my part, and these kinds of transactions can become a confusing "fun with numbers" exercise. Not so in this case. Chad was very straightforward and transparent throughout. I felt confident that I was working with a completely honest, and capable professional from start to finish. We agreed on a final price, and the deal was made. The paperwork part of these transactions often seem to take forever. I think I was in and out in under 2 hours from the moment I walked in, to the moment I drove off...With my new (used) car...! I highly recommend Oswego Motors. I believe they are a committed and discerning group of professionals who have a great collection of high quality cars selected to meet the demands of the marketplace. If you are looking for a great used vehicle, do yourself a favor...Give Oswego Motors a call. I'm glad I did.

The Mercedes-Benz SL55 is surely one of the most beautiful cars ever produced! From the jutting chin of its front bumper to its four-eyed headlamps; from its racy front fender air intakes to the sexy shoulders over its rear tires, the SL55 was not only the style leader for Mercedes-Benz but for the entire high-performance roadster segment.

Outstanding dealership!! They have a meticulously selected inventory of phenomenal luxury, classic and high-end vehicles at great prices. After searching for months, I was fortunate to find a muscle car gem at Platinum Motorsports – a very low-mile 2001 Camaro SS 6-speed in excellent condition for being 20+ years old! The guys there are all top-notch in the business; they genuinely care about their clients and are not just in it to make a quick sale. Manny, Zico and Rick have high integrity, are very communicative and helpful, and went above and beyond to get my new ride shipped to me promptly (even in the middle of a Chicago blizzard!) I can't say enough good things about the crew there, and I enthusiastically recommend them. If you’re thinking of buying one of the outstanding vehicles you see on their site, do it – you won’t regret it!!

To be honest this is a Renntech 550 but it is a beast. I tuned it among other things. I didn't badge it, makes it a bit more fun

I had really bad luck at every other dealer due to credit issues, I came here and they made me feel very comfortable and never seemed judgemental to my situation. They showed me every car i wanted to see, and told me all my options. best car lot experience overall . Recommend david, he was awesome

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...

The sales manager, Jeff, contacted us right away and was very responsive and helpful. Purchased vehicle and shipped it to us in a couple days. Happy with experience. Would recommend and would buy from this dealership again.

My 2014 SL550 has been absolutely trouble free. It's actually one of the most reliable cars I've ever owned. I live in Denver and frequently travel to Winter Park which involves a twisty mountain pass that crosses the Continental Divide. During summer months, I'll drive this car and the handling capabilities of the car allow it to shine. It's extremely agile and corners like a 911, with similar power (insane power to weight ratio from the twin-turbo V8, with all aluminum frame and body construction). Let's just say I like to drive in a spirited manner, and demand a lot from a car's power and handling. This car's capabilities are vastly unknown by the general public. To put it in perspective, no stock Mustang, Camaro, Charger, or Tesla has ever beaten me off the light in this car, and they sure try. I'm convinced every Tesla owner seems to just think their car is faster than ANY other car out there, and it's most definitely not. I frequently have Tesla drivers want to race me from a light in this car. The juvenile in me comes out and smokes them every time. The styling of this car might be controversial to some, but wherever you go or park, I've never had a car where so many people get giddy with excitement over how great they think it looks. Be ready for that...lol

OVER 600 CARS IN STOCK! Ask for GEORGE for best customer service... GREAT PRICES AROUND!

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!

Great people and a good environment. Everyone was very helpful and easy to work with. Very happy with how everything went and would not hesitate to purchase another vehicle with them

This car is a great cruiser with plenty of power and handling to keep it fun. If you are looking for a lively sports car, buy a Porsche, but if you are looking for a fantastic luxury sports convertible, there is no better car. This car is absolutely packed with every option you can image to make you drive pleasant. With the top down at 80mph and the windows up, there is virtually no wind in the cockpit. On cool nights, turn on the airscarf to blow warm air on your neck. The driving experience is impressive. The suspension system creates the illusion of a much lighter car when needed, but gives you that rock solid, heavy Mercedes ride always. This is no light weight machine. The V8 is smooth, but not chest-pressingly quick. Think locomotive, rather than racecar. That is not to say it is slow, but in this day and age of twin turbos, the normally aspirated SL is much more linear in the way it gets to 100mph. All that said, there are some things that Mercedes forgot in 2011. Generally speaking, the interface that houses the navigation system, radio, phone, etc is difficult and not intuitive. As well, the phone interface is maddening and the mic is noise sensitive (not a great feature in a convertible). Lastly, the gas mileage is measured in feet not miles (I average 14.7mpg to work). But, in a car that automatically turns on the air conditioned seats when you remotely put the top down and is powered by a creamy V8 mounted on a truly mind-blowing suspension, the minus fall away pretty fast. After all, this is a Mercedes SL.

Kris was outstanding to work with for the purchase of a used BMW X5. We felt no pressure as he made it clear he didn't work for commissions and steered us into the right car for us. It was a great experience all around. Thanks Kris!

Although this car is not my everyday car (for that I kept my Toyota Corolla), it is definitely perfect for pleasure! Drop the top and take off. It is definitely luxury. It was very low mileage for a 2007, but very clean -- almost new -- and beautiful! It rides beautifully. Hugs the road and you cannot feel bumps -- so smooth! It does have a lot of power, though, so not for the faint of heart or the youngsters! The sound system is fabulous, too. Have been enjoying driving this more than I could have ever imagined. Cannot imagine ever getting rid of this car -- just wish I would have found it sooner! Actually pretty comfortable, too. Love the dual climate controls and the messaging seats. We are going to be driving it from Virginia to Iowa to visit my family soon and looking forward to the fun and frolic with this little beauty!

Waiting to get back home to do the deal so sharpen your pencil I’m coming for the 2013 red Mercedes

This car was in excellent condition. 22,000 miles clean car fax. One owner. No dings great leather. Changed to 550 in 07 from SL 500 on 06. Quick enough!! All I’ve done is change out ALL FLUIDS. Cost a bit to do. Overall elated with purchase

Very responsive. Very knowledgeable about the Tesla Model S Plaid. Friendly and great communications from the first phone call to the last.

MBZ has been making the SL for 50+ years and the build quality, style and performance are excellent. If you are looking for a top of the line hard top that converts to a convertible, I highly recommend you test drive an SL.

Barry at Icars of Chicago has been phenomenal since day one, and he truly shines even a year after I bought my car. When I reached out with a follow-up issue, he didn’t hesitate—he jumped in, listened carefully, and helped me get things sorted quickly. It’s rare to find a dealer that stays engaged long after the sale, and Barry embodies that in every interaction. What stands out most is how they stand behind what they sell. I felt supported and respected from the moment I walked in, and that commitment hasn’t faded over time. The team’s customer service is second to none—honest, responsive, and genuinely invested in making sure you’re happy with your purchase. Their focus on building long-term relationships, not just closing a deal, is the best I’ve seen anywhere. If you’re shopping for a car and want a dealership that treats you like family while delivering real value and ongoing support, I’d absolutely recommend Icars of Chicago and Barry in particular. Their customer retention is unmatched, and that peace of mind is priceless.

We purchased this vehicle from the owner who had it for 11 years. It was meticulously maintained and only has 42,000 miles. I drove it home for over 150 miles. The car was incredibly comfortable and the gas mileage on the highway was about 25 miles per gallon. We are enjoying the car and I can’t wait for the cool months in south Florida to put that top down. I am glad we got this car and I think we will keep it for a long time.

Thanks it was a great night and thanks again to all of you at the Dealership for the help me in the BMW that you let me test drive and driving it now. Thanks again

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.

Great deals nice dealer . My wife did most of the negotiation over the phone but we did end up going in . They beat the an offer carmax gave us and took our trade . Good experience!

Extremely powerful, but comfortable even at a casual pace. Makes roads seem somehow smoother, even with firm, sporty ride and handling. Amazing car. This is my second one.

Was in and out very quick they answered all my questions. Even gave me a full detail and a full tank of gas

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.

Come see, he is very frienly and attentive, a good place to buy and shop.

I'm reviewing the SL600 with AMG package. First of all, it is an absolute blast to drive! Incredibly fast and responsive, and handles like a dream. Goes around corners like it's on rails. The handling is precise and it will out "sport" most sports cars, yet the ride is silky smooth. Don't be fooled by the naysayers who complain that it's "too heavy and luxurious". When you push it, it's an absolute rocket ship. Imho it also may be one of the best looking cars ever built, whether the top is up or down. Every line from every angle is sleek and curvy. As far as maintenance goes, just maintain it well and it'll treat you well. If you don't maintain it yourself, find a mechanic who knows the V-12. Stay away from the dealers and from your local mechanic who's not familiar with it. And don't forget to change the hydraulic fluid periodically, contrary to what the Mercedes dealers will tell you.

I found this place on google after searching for a new car for me to buy. Fortunately, the last car I bought for $17,300 was totaled (minor fender bender but airbags went off) and valued at $19,200 by insurance, meaning I had a good chunk towards a different car. I emailed Jasin about this 2016 X5 50i since it caught my eye with all of the packages and features it has and I got a reply within 25 minutes of doing so. The process was made very simple and to the point which I appreciate. When I get to Skokie he had everything already signed on his end so all I had to do was sign my parts, and after the test drive and some small talk about the car, I bought it and was in and out of the dealership within 45 minutes. The car is extremely clean and inside and out and there is zero issues with it. If anyone is looking to get a car without all of the hassle I highly recommend iCars Chicago. I’m very happy with my purchase

I've enjoyed all 3 of the SL's I've had over the last 22 years starting with the 97 SL 500 and now it's time to upgrade my 2011 to the new blunt front end that came out in 2012; I did not like the look, however it grows on you. I'm retired now so no more new SL's, but a low mileage 2014 or 2015 will do nicely as I don't like the 2016 front end, yet. The reason for the blunt front end is the European Union Pedestrian Impact Regulations that were announced back in 2005; it's to protect pedestrians from up to 25 MPH hits, so no more pointy front ends.

Bought a car for my Daughter, needed radio / GPS integrated system replaced. We took the car and they stood behind the repair of the car. The car is great and my Daughter is extremely happy with her car. I brought the car in for service and they said I didn’t need some of the services I requested which saved me money. They are honest and very nice to deal with.

easy to drive,fun car with top down plenty of performance.classic body style should hold its value and appreciate over time. great collector car . buy it.