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

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.

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 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.

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.

Just had my 2024 Jeep Grand Cherokee serviced at Castlevand Kim was my service consultant. She was vey helpful, service completed when promised and she covered the services and that my car was washed and ready!

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

Motor Cars of Chicago is a great dealership to work with! I purchased a used Dodge 3500 there and was provided a wonderful experience from the moment I walked in the door. Mark assisted me through the process and was helpful and very pleasant to work with! Highly recommend Mark AND this dealership!

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 would 100% recommend this dealership to anyone buying a car! It was my first time purchasing a vehicle and it went so smoothly thanks to the team at CDJR!

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.

The staff is all great! Wonderful experience! They always are great to us and give us outstanding deals. We would recommend this dealership to everyone.

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.

I got a great attention on all my needs they got service on all my cars 3 in total and treat my just like a family member

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).

Everyone at every level of the organization - be it sales, finance or service - were extremely professional with a top concern for customer service. We really appreciated this above all else.

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.

Good job Linus good job good job good job good job good job good job

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

Great people, selection and reasonable prices. I would recommend the dealership for new or used car purchases.

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 experience at McGrath Lexus of Westmont was spectacular. I purchased a 2016 Lexus Gs350. My sales representative Glen was great, honest and understanding. Was straight forward. From test drive to negotiating, to signing paperwork was quick and stress free.

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 a great experience with car shopping with Kendall Maxey, he had great knowledge with the whole process. I would highly recommend Castle Chevy to others!

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!

Mateen has been very helpful in our decision as to which vehicle to choose. He laid out options and scenarios that guided our decisions. Mateen was open to questions, he provided clear answers and has kept a pleasant and cheerful demeanor throughout our transaction that we left happy and content. Highly recommend him.

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.

A little hard to find but these guys are super easy going with no pressure. They had several trucks that were from the southern region of the country. The truck exceeded my husbands expectations. Great finance rates that were better than our own bank. We will without a doubt be back when we are ready for our next truck.

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.

Very easy to work with. They let me do any checks I wanted, and I did a lot. No surprises and the car was excellent. Very quick buying process and no hassles at all. Definitively recommend this place. Just with I had more time to look at all the truly amazing cars. It would have taken all day!

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.

Had my car serviced there (used car) & the staff was very nice, and communicated well. Had a small concern after i picked up my vehicle from service, but spoke with a team member who was very kind and explained what was to be expected after services. Would definitely recommend them to anyone.

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.

It was my first time buying a car and Cruz & David were very nice and got me a great price it was a great experience and in the future I would definitely go back and purchase another & I will recommend the place to all my friends and family

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 recently purchased a car here, and Dan made the car-buying process quick and easy. He was honest, attentive, and helpful every step of the way. I bought a highly special used car, and Dan's knowledge and guidance made me feel confident throughout the process. I'm very happy with my new car and the service I received. I would definitely recommend Dan and this dealership to anyone in the market for a vehicle.

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.

Alexander Lopez was great to work with, hopefully he sent that cup and shirt. Wonderful experience.

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!

Adam and Jorge and Jonathan helped with our 2 cars bought today thank you guys

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.