Used Jeep Grand Cherokee for sale near Oswego, IL under $650,000

Edit to prior review: We had an issue with a used CRV we bought there after a few days and had to bring it back but they did end up fixing it for us.

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.

Very informative and attentive, excellent customer service. Mike told me what time my truck would be ready and kept his word. Trustworthy!

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!

Friendly people in the building and outside the building too. It was nice to get coffee. Test drive was completed abd successful.

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.

Wonderful experience! Brian worked with us to find a car for me within my limited budget. We went through several test drives before we found the perfect fit. Brian was great-straightforward, patient, and pleasant throughout. The financing process was quick and enjoyable. The entire staff was accommodating, friendly, and fun even though the process kept everyone past closing. It's rare to be able to say you had a good time buying a car, but I can honestly say I did. I look forward to working with them again in the future and I highly recommend checking them out for your next car purchase.

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 was impressed by their honesty and straight forward pricing. Sales people don’t work on commission, so not pushy. I was in and out in 2.5 hours with my new car! And the price was exactly what was advertised on cars.com - no added costs once I arrived.

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

Second lease on a Grand Cherokee. Different than my 2021 in many ways. The all wheel drive makes the steering more sensitive. Tricky parking brake and much smaller layout of gauges in dash. No Sirius satilitte radio. Seats are harder. Overall better than the 2021.

Great experience salesman was awesome. Took only two hours from the time we got there till the time we were driving off the lot bought a really nice car for a low amount of money.

Great place. Up front honesty and not pushy at all. I would definitely return to purchase a vehicle here again.

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.

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.

Another excellent service experience with the dealership’s service staff; in this case, Service Advisor Roland and two porters, Manny and Jose! Roland addressed me immediately at my scheduled service appointment time, the inspectional and other need commenced, and Porters Manny and Jose provided transportation to and from my home during the efficient service of my vehicle (second one purchased through the dealership). Roland and the porters were attentive, professional, and friendly. Roland kept me apprised of the service process. DuPage Chrysler Dodge and Jeep is a winner!

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.

Overall a good experience with Ed Napleton Honda! Eric McGee was a great salesman and helped me and my sister in law purchase a vehicle. He met our every demand. I really just went to help my sister in law purchase a brand new vehicle, but I saw this Honda Crv and instantly knew I had to get it. So in other words Eric had a two car deal. I told him what I wanted in pricing for both vehicles and he said let me see what I can do and spoke with the sales manager and it was met to the T! If you're in the market, go with my guy Mr. Eric! He'll get you right!

This is third Jeep I have leased and best yet. Summit Reserve Trim is amazing. Great performance and many comfort features. Performance from the v8 Hemi is amazing.

I had a great experience buying my tesla from highline auto sales, specifically Scott. We were able to talk and text to negotiate a price both for the car I was buying, and the car I was selling. When I came in to test drive the vehicle, the car operated as expected. Once we got to the buying process, I was in and out of there in 45 minutes, with all the documents signed, and highline stuck to their word on the price we agreed upon on the phone. It was a flawless experience. Highly recommend them for a used tesla.

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.

Hi My my name is Rey Anguiano I want to thank Frank Bahena for the great experience i had , I will definitely stop in and purchase a vehicle pronmtly I will reconsider any one to visit by the dealership ask for this gentleman.

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.

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).

A remarkable buying experience! Jackson was responsive, informative, personal and NOT pushy. I am enjoying my new ride and have already recommended Chicago Motor Cars to my friends. Thank you for the quick turn around for a memorable Christmas surprise for my wife and family!

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.

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.

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 cannot recommend this dealership enough we had the best experience with Jason! His customer service was 10/10 I will definitely recommend Zeigler and Jason to anyone in the market to buy a car 10/10 recommend we will be back in the future!

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.

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

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.

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