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

From the moment I met Sales Executive Kelvin , I felt I was in good hands. He was warm and welcoming, making the entire process smooth and enjoyable. Overall, it was a professional and genuinely positive experience.

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.

The process was easy, the staff were pleasant and nice, and the service was efficient. Thank you Kelvin

The 2019 Grand Cherokee Limited was the Jeep I had my eye on for a while. I've owned a 2012 Laredo X, and a 2018 Limited Anniversary/Heritage Edition. I was specifically looking for Limited trim without the 20" rims, although, I love the look of the Altitude versions, I just didn't really care/want to deal with less side-wall, nicer-looking rims. I avoided the Overland and Trailhawk because of the air-suspension. Overall the interior is fine, it's comfortable and familiar for me, since I've owned them before, but that's also the only issue/complaint I would have. The interior is updated from the 2012, however, basically it's a very light update, U-Connect, Gauges, Shifter, and possibly a few other items here and there. But essentially, the dashboard is the same dashboard I've seen since 2012. While owning the previous (2) I never experienced any mechanical issues that left me stranded. One had a weird issue with blowing lights in the tailgate, but it would just randomly decide to burn out, replace one it would blow another. No other major issues. The 2019 leather on the steering wheel feels smooth and buttery like they always have. The suspension feels great, still solid and tight. Brakes are strong and grippy, pedal feel is nice and firm. So far I'm super satisfied with this Jeep, I got the perfect combination of all the features I wanted, Memory Seats, Sunroof, power trunk, heated-seats and wheel. Not sure if I'd be willing to sell this one and get a newer model, but, I'd possibly get another WK2.

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

2022 Grand Cherokee Overland. Beautiful inside and out. Love the extras that the Overland package provide. Beats EPA milage estimates easily. ride comfort is very good, even in the rear seats.

Awesome, Alex W. was great and had us laughing. They had the car ready and waiting for us outside when we got there ...overall a great experience with them.

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.

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.

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

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.

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.

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 !

PURCHASED A S63. IN AND OUT IN NO TIME. THEY HAVE A LUXURY SHOWROOM. THANKS RAY

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

Real curtious and knowledgeable staff I would tell my friends and family about this car lot

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).

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.

Thankyou Carlo Casini for working with me on my used car purchase. Thankyou To the rest of the crew for working with. To get my paper work completed.🙂

This is the 3rd Jeep product we have owned over the years, first was a Grand Cherokee Laredo, then most recently a 2012 Jeep Liberty Sport. We just purchased the 2019 Jeep Grand Cherokee Ltd in Febrary 2023. This Jeep is the most luxuary we've ever had in a vehicle, it has everything but the cooling seats which would be nice as we live in FL. This will be a dinghy towed vehicle behind our Class A motorhome. We also towed the Liberty Sport.

Very nice selection of cars.Their website was very helpful in searching for a car. Overall it was a hassle free experience buying our new Durango .

Bought my first Jeep Grand Cherokee in January of 2022. I was in a wreck where another vehicle hit me and threw me off the road into a ditch. I went airborne and came down hard. It was a miracle I did not flip. All of my driver-side airbags deployed (front and back) and I walked away with minor injuries. This vehicle kept me safe and I will have another one to replace the totaled Jeep from my wreck.

I purchased a great vehicle yesterday. The staff were all polite & friendly. Jorge was great.👏🏾He made sure I got what I was looking. I would definitely recommend him & Webb Chevy to anyone looking to purchase a vehicle.

Love my jeep. They have come a long way baby!! I am now a Jeep girl for life and recommend them highly. No matter the weather my Grand Cherokee gets me there in comfort and safety.

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.

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.

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

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.

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!

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.

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.

One of the best vehicles I have ever owned! Dependable, lots of features, stylish, fun to drive on and off road. A vehicle you can enjoy and be proud of!

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

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.

Good service good attention nice place to visit. I will add just one thing at the service shop, a bilingual employee thanks.

Have owned Jeeps for 35 years. This is the most comfortable ever. Altitude 4x2 L, V6, avg. 19-24 MPG. Tow up to 8,000. 6 passenger with 2 fold downs in back. Paid 34k with 18k miles