Used Jeep cars for sale near Winfield, IN under $899,990

Great working with this dealership, they are very helpful and easy to work with. They make the process very smooth, even for the buyer who dislikes car shopping.

We purchased a 2024 Jeep Compass Limited Elite. This vehicle has far surpassed our expectations for comfort, handling, road noise and quality. There is very little road noise we hear inside the vehicle, and this allows us to keep the radio turned down to a comfortable level. Handling is exceptional and very responsive. The driver safety features of lane guidance, adaptive cruise control (my favorite) and 360-degree backup camera are now features we will not go without after experiencing first hand performance. Thank you Jeep and Jeff Belzer CDJR of New Prague, MN

The customer service was great and very helpful, professional. Please give her a raise or take her out to lunch at the very least.

i recently had a 2023 for explorer it was a good truck never a problem but not a comfortable as the jeep grand Cherokee l front seating is amazing no issues at all i did my research and made sure i bought one with the German transmission its a good idea to check that only thing i can say on the down side seam to be a little under powered but i can live with it decent milage 20 around town.

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.

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 would highly recommend John Lipe and Robert Booth. Fair pricing, friendly people and great service.

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

They were nice and knowledgeable. Will return most likely. To but another vehicle from them.

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.

Thank you Bill, Chad, Jimmy, Brandon for taking care of Karen and me you guys are great and fun to be around thank you pearl

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.

Shopped for an SUV and found an excellent used car. No complaints and have had nothing but regular repairs. Buying process was fast and easy.

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.

Peter the salesman was courteous and professional. Very nice dealership! My wife did not like the interior color so we did not buy the car.

It is a great car, my uncle drove it in the west hamptons in New York to the beach. Very fun when the roof is not there.

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 🥰

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.

I had the best experience working with Neil, he answered all questions I had and was very low pressure , which was a nice change from a lot of dealers salespeople . On the day I came to pick up truck , Neil wasn’t working that day so he turned me over to Owen who was also awesome to deal with. I would recommend Fieldhouse Chrysler to anyone. Thanks for your help Mike Daly

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.

Great Customer Service and communication during your whole experience when you bring your vehicle in for maintenance. I really like it when they send you a video of all of the things they have checked in your vehicle. It gives you great info. Thanks to all. I love Castle Subaru.

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.

A nice place to buy a vehicle. Saleman Dominic was very professional. The establishment was very welcoming. Had a great experience there. Would definitely buy from again and recommend to friends and family.

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!

great customer service and get straight to the point of what you want or need

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.

A fair price was advertised for the used car we were looking for. It made it worth the trip for us to buy from Pearl. Nick and Chris were great to deal with. Very friendly and honest. The whole experience was low pressure and hassle free. The process was quick and easy.

I purchased a special ordered Jeep Wrangler RubiconX with the 3.6 engine from our local Dealership! When I first drove this this vehicle I knew it may be rough riding, but after having this for for over 6 months it now is our main vehicle for getting around town. I get 17.1-18.3mpg. It's a 4dr and we enjoy it every day for shopping and other chores. We had it on the main highway and do between 65 and 70mph. It handles great and the ride is actually pretty good. Has great passing power as it has 4:56 gearing! We just recently took our vehicle to Keene Dodge/Jeep to have the tires rotated and were very impressed with the service and the entire staff as they treated us very special.

When people complaining about the car buying process this wasn?t one of them they were great!!!

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.

As Steven Lyche was the best assistance I’ve received since doing business here, it makes me look forward to further business.

We bought it in 2023 just off lease as a CPO. It’s been a great vehicle. We love it would buy another one in a minute.

Brandon and the Manager were very helpful in helping me finding the right car for me.

I have had my 22 High Altitude for about 4 months now and the only issue(s) I find are the following: MPG is not as advertised, it's not that great. It's around 24 average, I am about 50/50 city/highway driving - It's fine. It DOES ride like a Jeep - so it's not as "luxurious" as your higher end cars, but YOU BOUGHT A JEEP - The last snow storm we had in Cleveland was about 10" in 2 hours - No problem, even with 235/45/19 tires - Would be way better with not so wide tires. It's slow. Who cares? Are you driving in the F1? Nah - It's plenty. Interior is baller. Infotainment is great, comfortable. Heated steering wheel is a plus. IDK - I read these reviews and everyone is so picky - It's a nice ride. If you find you like it, give it a shot.

They were excellent!! Quick and easy and very knowledgeable. Traveled two hours and it was worth the drive

I love my vehicle. It's a 2023 model year Jeep Grand Cherokee L in the Summit Reserve trim with the 5.7 liter HEMI V8 engine. Overall sleek exterior design of the vehicle is nice. As for the interior, it's great! Nice and comfortable interior. Palermo leather seats, massaging front seats and power folding rear seats. Heated/ventilated seats for both the first and second rows. Front passenger infotainment screen, interior camera, night vision camera, ambient lighting and a 19-speaker premium audio system. More importantly is the excellent performance. This V8 engine comes with 357 horsepower and 390 pound feet of torque. It'll go from 0-60 in 6.1 seconds. Very good acceleration for sure. A recommended vehicle for performance, enjoying features, hauling passengers and carrying big loads when seats are folded. 👍👍

Go see Joe, he is the best salesman!! cares about his customers he is kind and knows his stuff. If I ever bought a car again I would go back to see Joe. They gave me an IOU for things that needed to be fixed two little things and when I went in Joe was right there ready to help

An Outstanding Car Buying Experience at South Oak Dodge Chrysler Jeep Ram of Matteson, IL Our recent car buying experience at South Oak of Matteson, IL was nothing short of incredible, thanks to the exceptional help and expertise of Ryan Ganser, the Finance Manager, and Aaron Mathews, our Sales Professional. From the moment we walked in, Ryan and Aaron created a warm and welcoming environment. Their knowledge and informative approach made us feel confident and well-guided throughout the entire process. Ryan's financial expertise ensured everything was seamless, while Aaron's professionalism and personable manner made us feel valued as customers. We left with not just a vehicle we love, but also the joy of knowing we made the right choice with South Oak. We would highly recommend Aaron Mathews and Ryan Ganser to anyone in the market for purchasing a vehicle—they truly set the standard for customer service and excellence.

My only complaint are the front seats do not have enough cushion and the seatbelt latch pushes into your hip on the drivers side. and standard lumbar support on all models added