Used Jeep Grand Cherokee for sale near Winnetka, IL under $899,990

I initially bought my car in July 2022. Our old family car broke down and needed a car. I had been window shopping for cars and looked but I didn?t see a car that stuck out to me until I saw the Buick Envision and fell in love with it and the color. The staff was super helpful throughout the buying process and I?m super happy with my purchase, I haven?t had my first oil change yet but I will def get that done soon at my dealer.

This is my first Jeep I have ever owned. I always liked the looks of the Grand Cherokee. I’m happy with the vehicle. No complaints except it does like to drink gasoline. My previous 4 vehicles were all 8 cylinder full size pickup trucks. The Jeep being a 6 cylinder eats more gas. The Other than that, I’m very happy with my purchase of my 2022 Jeep Grand Cherokee. Good looks, drives well, comfortable and safe.

I had the pleasure of being assisted by Sam, and he was amazing. He wasn’t pushy at all and answered every question I had with confidence and clarity. He was friendly, approachable, and made the whole experience comfortable and easy. Great service all around.

I purchased it used in 2022, it had 76k and now has 96 in 2025. It's 4wd with the 5.7 Hemi in the Overland trim. It hasn't given me any trouble.

My first car-buying experience was great! I worked with Dominic and Vince. They both were incredibly helpful, supportive, and patient throughout the process. Dominic was very knowledgeable about the vehicles I was considering and took his time answering my questions. Got a really good deal and they helped me get the car I was looking for and the payment I could afford. Dominic really considered all of the information I gave him and was completely professional the whole time. I’m very satisfied with my purchase. Truly the best experience for being a first time car buyer.

We purchased our 2014 Grand Cherokee Overland new and after 11 years and almost 150,000 miles it easily the BEST vehicle we have ever owned. It is comfortable, delivers reasonable mileage, is quiet, well built, incredibly durable and looks as good today as the day we took delivery.

Awesome Is the experience that I have had throughout all of my carbon experiences at car max We've bought 2 cars from them and sold them one car miss Sherman is an awesome sales rep very thorough very honest very respectful

Runs smooth. Very comfortable. Always loved the Jeep brand so this was a natural upgrade. Love the options too. The adaptive cruise control is amazing.

Joe was our sales associate. He was very knowledgeable and helpful. He was very patient and guided me into the process of purchasing my first car. This definitely helped me solidly my decision of buying the car with this dealership as he was very attentive and willing to help us. Overall, the process was fairly quick and smooth. Great experience and will definitely recommend to others.

bought a new 2022 GC Summit. I wanted the hemi, only found it in Summit pkg at the time. Overall love the vehicle interior is as nice as anything out there. Real wood, lots of leather and nice materials overall on interior. Kicking stereo. Had a 2016 Overland with hemi. Wanted one more new hemi before quit making them. Easy 20-22 mpg at 70 mph. Plenty of power, very quiet and smooth. Biggest complaint all the plastic trim on the outside. First time i shut the door sounded like a rattle or something, not as solid as the 2016, when i shut the door it sounded solid. Nothing i could find wrong just pieces seeming to make a noise. Overall love it. Looks great, rides great, descent mileage, and very nice interior. Did i mention messaging seats are real sweet. Also plenty of towing power which i needed. Excellent in the snow as well.

my wife and i came in to look at the mini cooper we saw online and we were very happy with the service we were given. From the time of first contact with danny we were very happy so happy with windy city motors that my wife made the purchase of a 2007 mini cooper convertible. Everybody was very friendly and courteous and we will be more than happy to deal with windy city motors in the future if need be thank you windy city motors

Bought one for my son for college. Had 108K, now as 190K. Can't complaint. Safe, reliable and very comfortable. Did have to replace the oil cooler assembly, but that's a given on a 3.6. Other than that, tires, brake pads, the usual. It's been a winner.

Took my mom to buy a pre-driven Camry. Car was there, clean, and ready to go. Test Drove, no issues. In and out fast, no games. No pressure. Good Sales Price. Worked with Mike Rubino, good experience! Would Highly Recommend Him!

New Jeep GC owner…about a month in. Bought a ‘23 Grand Cherokee Summit after admiring the looks of it. Was nervous to purchase because I usually drive foreign. I also own a ‘22 Audi and have to say that the quality of my Jeep is comparable. I am pleasantly surprised by the drive as well as the quality of the finishes. The ride is quiet and smooth. The 6 cylinder has plenty of pep and has no trouble getting down the highway. It even has a bit of a growl when you step down on it. I legit smile every time I drive my Jeep.

2017 GC Limited 4WD. Bought it 3 years ago with 53k miles and now approaching 108k miles. When we bought it, we went to fill the tank for the first time and the gas pump kept shutting off. Turns out there was a known issue with the fuel filler neck assembly. The selling dealer replaced it under warranty and we literally didn't have another issue until 100k miles. At 100k miles took it in for new spark plugs, which is normal maintenance, and found the radiator leaking. The new radiator was not cheap. Have not had any other issues, just replaced the factory original brakes, they made it almost to 108k! We live in Minnesota and this vehicle is an absolute beast in the snow. Put it in snow mode and it is very stable and feels unstoppable. It is a comfortable long distance cruiser and gets decent mileage on the highway, between 24-27mpg. The UConnect system is very easy to use, and the nav is pretty good, but the whole system operates quite slowly. That's a minor complaint I think. Overall we are pretty happy with our WK2.

Purchase my brand new 2025 jeep compass with nestor he was the best help got me in and out Quick other dealerships couldnt get me approved anywhere else and they made it happen big thanks to the manager Chuck as well if you are looking for a car come and así for nestor

What a great look. I have bought several cars and trucks over the past few years, from 2 trucks for me and helped the family with other cars. I wanted to get something for looks and the 2025 Grand Cherokee fit the bill. Style and looks, 10 out of 10 in my opinion. Good on the mileage and performance. Great dealership and people at Ray's CDJR in Fox Lake. They treat you like you should be, with respect through the entire process.

Ramy gave me the best service today and I came away with a car at a great price. He wasn't pushy and let me make my own decisions. A lovely down to earth guy :)

Bought my 2017 Overland 2WD preowned with 74k miles. It’s now Feb of 2024 my Jeep’s got 135k on the odometer and I’ve never once had an issue. I occasionally get car fever, start looking at cars online, but the second I jump behind the wheel of my Grand Cherokee I smile and decide to keep it for a little longer. I still love the look, it’s super comfortable, has plenty of power, all the bells and whistles I want (and beyond), and I love the fact not every single thing is touch screen as most modern vehicles. I love I can turn up the volume, operate the AC and many features with good ‘ole KNOBS without taking my eyes off the road.

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

I've owned 3 Jeep products (2 Cherokees, and 1 Wrangler) and bought Cherokees 3 for my kids. Now they bought their own. Reliable, durable, and affordable. I love my 2017 Altitude. Looks great. The only thing I had to replace was a water pump at 80,000 miles.

I went in to buy my first car, and even though it took longer than I thought lol. I must say it was an great experience Mason was very,very helpful and with everything! I got my keys the same day.

I just love everything about my 2021 80th anniversary edition G/C! I purchased new but now has 81000km. So much enjoy all the style comfort with no issues. So much more reliable and better looking than the new body style that was released later in 2021.

Jose, Josh and Alex were very professional and very attentive to my needs. I appreciated all the help they gave me. Excellent customer service. Thank you guys!

Because it a great car because the car has 118k miles on it and its only 15,371 dollars and its used and works very well

Customer service one of the best AJ was very helpful I been a customer for years I will definitely recommend this place to anyone.

I've been driving for 43 years now and have owned an array of different vehicles, however I've never been financially fortunate to purchase a luxury model - until now! I was looking for a mid size vehicle that would check many boxes for my snowy Michigan commutes, along with distant travel comfort to and from my cabin and some towing capacity. I have only had this for roughly 1500 miles and wow.. My first impression was luxury. So many base options included in a mid sized and mid priced SUV that pleasantly surprised me. Secondly was the ride quality. Both smooth and quiet and handling. I've read other reviews discussing power inadequacy, but not at all. Plenty of passing and get tup to speed power. Next was the snow. I have Michelin defender tires and wow - what have I been missing? The snow 4x4 duaratac features combined with these tires make this a beast in the snow, slush and rain. It definitely gives me a much more safety reassurance while driving in these conditions. I have not tried the towing yet and have not had any "reliable" issues to report, but we are very fortunate with our pick and one very capable snow commuter.

Excellent experience with Doug and the whole team here! I knew what I wanted when I came in and they helped me find the right car at the right price! I would recommend them to anyone!

I HATE is the warning 'Place Two Hands On Wheel' as it goes off even when I have both hands on the wheel - No matter where I place my hands on the wheel it goes off. Since it is connected to the Lane Departure feature in order to not have to hear a constant warning alarm for Two Hands on Wheel I have to turn off the Lane Departure feature (which I love).

Kenad and Drudar were wonderful to work with. They went out of their way to meet our needs. Keep up the good work.

My Grand Cherokee Laredo E just turned 50,000 miles a few days ago. Other than routine maintenance, the only money that I have invested in it was for 4 tires last month. Extremely comfortable, capable and reliable. While not delivering Prius-like gas mileage, given the performance it provides in all types of weather.............NO COMPLAINTS !

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.

We just bought a 2023 JGC Limited for my wife. I had to decide whether to trade in my 2015 Caravan with 50K miles, or her 2011 JGC Limited with 93K miles. Which would you decide to do? I chose to keep the Jeep and I think I made the right choice. The Jeep has the Hemi and fully loaded. We bought it new in 2011 and she treated it with much love. She had a few minor problems and it looks like new. My plan is to keep her to 200K+ miles. I love the 2011 style even better than her new '23. And there is the HEMI. I would not hesitate to buy a used JGC with the Hemi engine, BUT it would have to be a one owner with service records.

Called and spoke to Frank and he was so pleasant that I had to go. Yourself got me into the Jeep I wanted and worked so hard to get the best rate possible! Don’t sleep on this dealership! You won’t be disappointed!

We are very happy with our '21 GC Limited. It is well appointed, with many options, drives nice, comfortable and still sits higher, unlike a lot of other "car" SUV's. We use this as our only vehicle, and flat tow behind our motorhome. Jeeps are the best vehicles made to flat tow!! We have climbed dirt trails in the West and cruised coastal waterways. Love it.

Ernie was a great salesman he walks you through eve step of the process

Besides the hefty amount of recalls in the first year, overall has been the best Jeep I’ve owned. Super comfortable, very reliable in weather conditions. Can sit in it for 6+ hours a day without my back hurting (I have a rod in my back). Traded a hellcat for more comfort. It was worth it. Probably best adult decision I’ve made. Does pretty well on gas. (3.6L) I get about 584 range, sometimes 598 depending on how traffic is. However the interior could have been constructed of better materials. (Steering wheel stitching came lose but covered under warranty). Had it since end of March 23 with 25k miles already. No huge issues, never had to worry about screen issues (like what I’ve heard about 21-22 models). I would recommend this vehicle to anyone who is looking for an upgrade from previous body style GC, bigger suv with legroom, and enjoyable drive. I test drove a RAV4, CR-V. Ended up buying a 23 Jeep. Most vehicles in the market don’t have the technology the Jeep has. Toyota is a few years behind (& the road noise is unbearable), CR-V doesn’t have enough pep in its step ( Also the interior gives off impoverished/ barely any enjoyable features and buttons. Jeep is perfect. I love how a lot of options are in the screen but also below the screen. Not too cluttered.

Alex was very professional ans I got to leave with my car very helpful go to him he will help you

I have that car and I’m happy with it. Yes it have some problems, need some care, you can just go to speedway and fuel up it would be your last fuel up with diesel on speedway. To previous review: I bought the car with 185000 miles. After I fuel up at speedway 😁, I sen car to dealership. They replace entire emission system with brand new. No problems after that. Just fuel up at good stations, I prefer Sheetz or BP or shell. About $300 oil changes: I do my oil changes by my self: 2, 5 quart oil canisters and $25 filter and it’s don for $75. I change oil every 5k miles. About fuel filters: I do it by myself too. So 2 filters on Amazon for $17-25 and you have done it for $35-50. I change them every 20k miles.