Used Jeep Grand Cherokee for sale near Whiting, IN under $899,990

I want to thank Joe Collins for the wonderful service I received today. From the time I arrived I was welcomed with a smile and knowledgeable service. Joe and the technicians that serviced my Caravan today I want to say Thank you. Someone asked me why I bring my vehicle here for service this is why! I would recommend Castle Chrysler Dodge Ram of Chesterton. I have been a customer now for over 5yrs. and they have always been top notch. You have earned a 5star from me. That's why I'll always return. Happy Holidays to the entire staff and especially to Joe Collins for all your kindness 🥰

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 initially checked to see if the SUV I found on cars.com was still available to look at. After sending the email, via cars.com, I got a text back within a few minutes saying the SUV was available and a salesperson would check with me to set up an appointment. I spoke with Jamie shortly thereafter and met with her at the dealership. The SUV was washed and ready for me to see and test drive. The rest of the purchase experience was fantastic!! For me, number one of the top three car buying experiences ever. I’m now retired and have bought a lot of cars. No high pressure, just great customer service. Keep up the great work Jamie and Bettenhausen!

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.

5 stars – Honest, efficient, and the reason I came back This was my second time working with Josh Hendrix, and I specifically came back because of how straightforward he is. We were buying a car for my daughter, and I appreciated that Josh didn’t push, didn’t upsell, and didn’t waste our time. He gave us a fair offer from the start and made the process easy. After dealing with salespeople at other dealerships who overtalk or dodge questions, Josh is someone I trust. If you’re buying a car, especially for family, he’s the one to work with.

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.

Working with Castle Jeep was simply awesome. I have never had a better experience at a dealership. Josh and Tony did such a great job working with me. I don’t have enough good things to say about them.

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).

We bought a nice RAV4 from Team with the help from Rick who did a great job with helping us with selecting a vehicle, very happy with our new vehicle.

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.

"Jakub Sales delivers exceptional service, exceeding expectations with top-notch quality and professionalism. Highly recommended!"

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.

⭐⭐⭐☆☆ (3/5 Stars) I had a great initial experience with Highline Autos. The transaction was fast, smooth, and professionally handled. The team—especially Zuhair, the owner, and the young Ghalib—was responsive and knowledgeable, making the buying process straightforward and low-stress. Their professionalism and business reliability stood out during the deal. However, about a week later, I was disappointed to discover that the tires on the car I purchased were leaking. Upon inspection, it turned out that plugs had been used as a temporary fix rather than properly addressing the issue. This was unexpected and concerning, as I had hoped for greater transparency regarding the vehicle's condition. While I appreciated the efficiency and service during the sale, I hope the team takes this feedback seriously and ensures that future vehicles are fully inspected and represented. I’d encourage potential buyers to have a thorough inspection before finalizing a purchase.

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.

I bought my second truck in 4 years from Bose. The first was a champ. It did all I asked of it and remained reliable the entire time I owned it. I needed more weight and tow capacity and ended up back at Bose. Same great experience as the first time. The sales staff was helpful, open and directly answered my questions. I never experienced any evasion from them or doubt that they are being truthful. Their assistance with financing was great. It's been three months and after a few maintenance stops and a new set of tires, I'm very happy with this truck. Understand you're buying used and plan accordingly. If you want perfect, buy new. Although that's no guarantee either. Good, solid vehicles at a decent price. I absolutely will return to Bose should I be in the market for another vehicle. Incidentally, the first truck is still in the family being a reliable hauler. Can't beat that!

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.

Sam and the Team at Hinsdale Land Rover were great. He was patient with me and answered all my questions clearly and did what he said he would do. 3 purchase from Hinsdale Land Rover and a great service team as well

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.

Thank you to Teresita and Money Carlos they were great and provided great customer service to our family. We love our new 2018 Journey! Keep doing a great job friends!

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

Went in on Saturday and sat across from Mike in sales. I knew what I wanted. They had it. And offered it at a fair price. After the test drive he ran some high level financing numbers and we agreed on an overall purchase price and my trade in price. But before we agreed I told him I want to be OUT THE DOOR ASAP. No extra conversations. No additional warranty sales pitches from finance. Let’s get this done. Scott the manager came over and told me he’d do everything he could to expedite the process from this point forward but they were pretty busy (being Saturday). All said and done they’d washed the car, put in some more gas, sync’d my phone to the car, and ordered a vial of touch up paint while I did the paperwork with the finance guy. Like promised -in and out in about 90 minutes total. Very happy and would recommend the whole team!

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 !

So this was my first new vehicle purchase as well as being my first truck. Jake was very informative and efficient with the buying process. Big shout out to Walter too for crunching numbers and getting me the best rate like a beast! Would definitely buy from Phillips again!

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.

Stitch was very patient with me and made sure all of my questions were answered. If she did not have the answer she asked right away. She is great.

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!

I want to note this dealership as one of the best, with flexible prices and professional staff. I especially want to note sales guides: Agnes Landowski and Dennis Azarov. They have proven themselves not only as good advisors in financial matters but also as experts in the technical features of cars.

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.

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

Nice hellcat red eye jeep Chrysler ram good drive suspension engine and supercharger. Great exhaust 6 seconds on track and review 5 star safety rating

Néstor hélped me purchased my new 2023 Nissan rogué súper exicited for my new vehícle if you are looking for a car ask for Nestor got me a approved and With Payments that I was súper happy with

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.

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

Our salesperson was Faye. She was laid back and not pushy. I really appreciate her patience with us. We gave her a price point and she helped us to reach it. I wish all sales people were as professional and personable as she is. We would definitely recommend her and your staff for our future needs.

Good customer service, very polite, nice vehicle. A very clean establishment. I would recommend this company. I hope nothing does not change my mind.

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.

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.