Used Mercedes-Benz SL-Class for sale near Chicago, IL under $750,000

Colin help me find the perfect back to school car it was in super nice shape and they gave me such a good deal. I would definitely come back once I need a new vehicle. Thanks Ace motor works team

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 had a really good experience with Guaranteed Motor Cars. The whole process was smooth, no pressure, and they were upfront about everything. The staff was helpful and made sure I left confident in my purchase. Definitely 100% recommend them if you’re looking for a solid car buying experience.

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!

Excellent Cust service!! Yassin was phenomenal and made sure that all of our concerns were addressed and taken care of.

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!

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

I haven't seen a car yet but the sales person I spoke with was cordial and accommodating

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!

What an incredible car dealer. Purchased a car and they have absolutely gone above and beyond all expectations. The sales process was wonderful and then when we needed a little warranty work, so fast and professional. Made the whole experience the best vehicle purchase in my lifetime. Well Done and Thank you so much!

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

Everything was great . Andrew was great. I had no problems . All the people I meet were amazing.

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.

Had an opportunity to buy a car for my son and we stopped in to Oswego Motors. They were very helpful in know our price range and what we were looking for. We were not able to find on site they went out and found a vehicle that was perfect for our son. Safe, affordable and good size. The staff communicated well and helped us along this journey.

Always wanted an sl55 amg and finally found one for a reasonable price. The ABC suspension is a huge expense but the car is solid aside from that. With a few modifications and consistent upkeep this car will be a classic sports car for years to come.

I had a wonderful car buying experience at Tab Auto Brokers. I am a first-time car buyer and Todd, the owner, went above and beyond with his transparency of the vehicle and helping me understand the process. He also gave me time to get things in order to purchase the vehicle; something I know would never happen at a typical dealership. 10/10 customer service, car and experience!

I've had my '03 SL55 since new. It was one of the 1st US delivery cars. 19 years later it still is a gem. Looks amazing, performance from the 500hp V8 is brilliant. I really haven't had very many problems during my ownership. The worst part is depreciation. Mine was $130K out the door. Since I am not planning to sell, I haven't lost a penny. The problem with depreciation is as they get cheaper to buy, the bottom feeders swoop in, but they can't afford to maintain the $130K car they just bought for $30K. This will leave fewer and fewer good cars. If the SL55 is on your radar, buy the best car you can afford, have it inspected by someone who knows these cars and be prepared to maintain it like the $130K car that it is and it will reward you like very few cars can.

I can't tell you what a privilege it was to find and buy a car at this small auto store. Leo was above and beyond what EVERY reputable dealer should strive to be; honest, straight to the point, and most importantly, fair! I was literally in and out within 20 minutes of taking the test drive which is the fastest I've ever purchased a car. He went above and beyond and I will forever be grateful. His store will be the first place I recommend people to check out before anyone else.

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!

I had a wonderful and enjoyable experience purchasing a car with Auto Park Imports. The team was proffesional and efficient, couldn’t be happier with the 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.

I purchased a car in early April and I had a pleasant experience. Mike the owner/manager of the facility ensured that any concerns that I may have had were addressed promptly. I’ll for sure look to purchase here in the future.

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...

My experience was extremely pleasant and Jake was very helpful and he worked efficiently and got me out in a timely manner!

This car is the perfect car. Its ready for anything and occasion. A drive to the beach is the greatest thing to do with this car

Great experience, quick to set up, check in and out and everything was quoted with pricing. Time was appropriate for the amount of work done

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

Great experience got a beautiful Corvette out of the deal would recommend them to anyone

This Mercedes was above other Sports Cars I've owned. All of the Power Functions were reliable, good acceleration when needed. Could sustain speed with little, if any effort. Comfortable, no matter how long the trip. Expensive to repair, should something go wrong, is the only drawback..

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.

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.

I purchased a 2008 CL 550 that I absolutely love. It drives almost like it’s brand new despite being 18 years old. My salesman Chris went above and beyond with getting me in this car and even fixed the air conditioner on another vehicle I drove there to buy this car! I’ve never had that happen before. My future car purchases will be with him and this dealership!

My 2005 sl has been nothing but great! The inerior is just about perfect, and the exterior shines better than new. ONE notoriours problem is with the leveling system. Mine as others started to sink to the left when garaged..yikes! I was quoted around $3500 to fix it, but I found a great mechanic to do this for $800 including other maintenence. Thus car handles like a dream. Top up or down, it has great appeal and I cant tell you with way Iike it best. You can steal one of these cheap too..but make sure the owner kept it nice! My interior is perfect, yet Ive seen others quite shabby.

My Sunday beach runner for two. Hard top/convertible, perfect for senior single to do day trips to the coast with a pal. While the maintenance will be a little higher, its perfect for a used grand touring roadster and so far its a blast and have had no issues. Certified Benz and Beemer, Scottsdale did a complete certification inspection and prep job. Out the door for under $20k.

A car that can provide exhilarating performance, and comfortable highway cruising. It simultaneously provides top up solidarity and safety with top down panache with beautiful elegance. The “experts” say it is heavy. It is, but some right foot snaps away that illusion. They squabble about “dead steering” and brakes that are a bit numb. But If you toss it into a turn or need to stop it , be assured it will perform with aplomb, without the fussy twitching of a boy-racer. All cars, even ones with $100,000+ price tags, are compromises between performance and comfort, nimbleness and stability. This car is not aimed at a testosterone-fueled owner clawing up the ladder, but rather a confident owner that needs to prove nothing other than to show up. And for me, that makes this car the perfect compromise. It never fails to bring a smile. Few machines provide this level of comfort, performance, and design quality. And if a machine can bring joy along with performance, hasn’t really done its job In a spectacular way?

Julian is a wonderful sales representative. He was thorough and an excellent communicator. Management also was through and brilliant with their communication. One of the easiest purchases I've ever made

This car is a dream. This is one of a kind and has been maintained at Mercedes and on time. That kept it running trouble free. It is a complex car with many systems that provide unmatched driving experience. Car is amazing. reading the manual and checking the fuses and relays are key. Many of the issues could be nothing than a bad fuse or relay. I won't drive anything else.