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

Salesperson Mark Gurgone was knowledgeable, professional, and easy to work with. The experience of buying a car is stressful, but I left feeling like I hadn’t gotten taken to the cleaners. I would work with him again.

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.

Dani and Joe are very professional and do fantastic work. You can't find a better deal!

I initially leased my Grand Cherokee Limited but ended up buying it outright at lease end. It has been an awesome vehicle for the 6 years I've had it. I have only had two minor things that have needed work, one was AC needed more coolant and leaking rear strut which must be a fairly common issue as my mom's Durango has had the same problem. Super comfortable ride and plenty of room. My only beef is the halogen factory lights are horrendous but swapping the bulbs out for LED made a big difference for under $200. I normally don't keep a vehicle for longer than 2 years, but after 6 I love this vehicle just as much today as did the day I ordered it!

Great service. Mechanic found a bubble in my tire. Very thankful because I was going on a trip next day. Thanks.

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.

Exceptional experience. The entire staff is professional, courteous, knowledgeable, and efficient. Service is always completed in a timely manner. As an added bonus the technician sends a live video to the customer as he is performing the vehicle’s diagnostics.

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.

Dealing with my sakes person Katherine was the best experience I have ever had Purchasing a new vehicle. From start to finish she kept us updated constantly on the vehicle we specially ordered. I wish every experience was as easy and pleasurable as this one.

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.

David’s attention was as good as all the folks in the Service Dept at Fields in Glenview. What a team! Gent named Brian has been fantastic to me as well. Roland and Laura, too. The gals at the Pay station, everybody. Love Field’s in Glenview. And love my 2014 Jeep Patriot Latitude!

My dream car since a teenager was a grand Cherokee and when I finally got one in 2021, I’ve loved it the same ever since. They are bold in appearance and look like a strong vehicle. It has always run beautifully and I have had no issues thus far since 2021 and now it’s 2024. Very comfortable interior and attractive to the eye. Love love love my car.

I found a car on cars.com on Saturday night. Message them on Sunday and lined up a test drive for 11AM Monday. The vehicle was extremely clean inside and out. We negotiated a price very quickly and it was the fastest car buying experience I've been involved with. It was worth the 2.5 hour drive. John, Dwayne, Tom and the rest of the team was awesome.

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

I have spent my entire life in and around the auto industry and these guys are the only dealer I buy from outside of my own. Dempsey isn't your typical car dealer, and the experience is far more laid back. If you are looking for Unique cars at fair prices, make this place your destination.

This is my 2nd Jeep Grand Cherokee (previous one was a 2016), and I absolutely love it. Gives a very smooth ride. The vehicle feels very sturdy and solid, which to me is another plus. Disappointed that it didn't come with a cargo cover though!

I saw a van listed on Carfax for this dealer. I filled out the request info page ad almost immediatley was contacted by Jesse, that was on a Sunday . Monday we went in and test drove the vehicle. There was no pressure to buy, no showing us more expensive vehicles. We were allowed to test drive without the salesman. Our salesman was Jim. He worked with us to get a payment we could afford. Only one minor hiccup. We were told there were 2 keys available ,but then after all was agreed on ,there was only one . we were told they would et us the second key. They would come pick up the van get the key programed and brig the van back( we are an hour away from the dealer. As promised key was ordered Tues ,Wed the van was picked up an new key was made . They kept the promise that they made.

My husband and I love our Grand Jeep Cherokee we purchased from Chrysler, Dodge, Jeep of Winter Haven. We love everything about this vehicle. Matt is our Salesman, and he did everything he could to get us in a Jeep we would like. I highly recommend this company.

Nice large inside showroom to shop in warmth. Good selection of vehicles. Welcoming staff! Salesman Eli was exceptionally helpful, and Manager Josh worked with me to close the deal.

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.

All in all this was a very pleasant car buying experience. Tom Dempsey, the owner of the dealership, personally found me the car I was looking for at the price I could afford. Elijah then took over and did an amazing job showing us how to operate all of the electronic features this car has. He was extremely professional and patient and he walked us through everything. I will recommend this dealership to all my friends.

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’ve called different places for jeep information but this place actually truly helped me a lot, he explained everything to me and broke everything down for me considering I don’t know much about cars. Definitely looking forward to coming in with David and potentially buying my first car!!!

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.

Best Group of Guys Ovidio very professional Excellent environment good selection easy and very hospitable

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.

Quick communication and smooth process. Ov Perez was very professional, helpful salesman who made the sale a great experience.

Bought the vehicle with 30,000 miles. Turned over 100,000 this week after four years. ZERO unplanned visits to the dealership. Just normal oil, filters, wipers. Since we tow a 3500-pound boat, decided to replace the brakes at 80,000 miles, turns out there was still plenty of material left. Infotainment screen developed minor delamination this spring. Was still working fine but decided to replace it anyway. Easy replacement job for $350 with YouTube help. Lowest maintenance vehicle we have ever owned.

Ovdio gracias si muy bien 100 percent awesome job 3 car there 5 m0re ovi

Love my GC 80th Anniversary Edition. A little over 15K miles and she’s been in the shop 2 times now with a squeaking coming from the engine. Tensioner rod and idle sensor were replaced first, they had it for almost a month. alternator was just replaced, they had it for a week. Picked her up last night, drove her this morning and it’s still squeaking! Very frustrated but hoping to get her fixed!

It was great my brother and Samuel Jackson had a very good talk and understanding . Samuel Jackson has been the one I sent my cousin, nice and now my fiance. Keep up the good work Samuel

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.

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.

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.

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.

Just bought a new Challenger Scat Pak from Rex at Tyson Motors in Shorewood. Rex was great to work with throughout the purchase process. His product knowledge is excellent without being pushy. If you want a Dodge product, call Rex!

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!