Used Jeep Grand Cherokee for sale near New Chicago, IN under $19,989

This is car number 8 with Midway Dodge. This is the only place we shop. We always receive great service from everyone here. Thank you for the great service especially Money Carlos

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.

My wife and I really appreciated the attention and concern from Joe the salesman who took an interest in finding the right vehicle to meet my needs and concerns about driving over 120 miles 5 days a week to get to and from work in South Bend. I wouldn?t buy a Ford from any other dealer!!! I?ve never been disappointed with the repair and maintenance we?ve receive at Currie Ford.

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.

Vera was very quick and polite. Great experience Very good pricing and deal was done fast and easy. Was in and out the door in about a hour.

Bought one for my son for college. Had 108K, now as 190K. Can't complaint. Safe, reliable and very comfortable. Did have to replace the oil cooler assembly, but that's a given on a 3.6. Other than that, tires, brake pads, the usual. It's been a winner.

Couldn’t have had a better buying experience than with John Kazminski. We love our new 2023 Atlas Cross Sport and would highly recommend John! Thanks 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.

I just purchased a car from Castle Hyundai of Oak Lawn, and I couldn’t be more grateful for the experience. From start to finish, the team showed true professionalism, care, and integrity—qualities that can be hard to come by in the car-buying world. Now I truly understand what they mean when they say “Drive Happy!” Jim (Sales Manager), Nick (Sales Consultant), Brennan (Internet Representative), and John (Finance Manager) were an absolute pleasure to work with. They went above and beyond to make sure I felt informed, respected, and supported throughout the process. They were transparent, never pushy, and always willing to answer my (many!) questions with patience and honesty. It was clear that they genuinely cared—about the car, the deal, and most importantly, about me as a customer. They didn’t just meet expectations - they exceeded them. The entire process was smooth, respectful, and even enjoyable. These are good people who take pride in doing right by others. Thank you to everyone at Castle Hyundai of Oak Lawn—you didn’t just help me get a great car, you made the whole experience one to remember. You went the extra mile (pun absolutely intended) and because of you, I now Drive Happy!

The 2012 Gran Cherokee Overland has been my car for over 12 years. I’ve enjoyed every minute of driving it. Have made several road trips with it and never a complaint. It’s plush with features and luxury items. Love the looks, love the ride, love the comfort and love the low cost of ownership. Jeep lives up to its name and fame.

Cheyenne Fontanez is the best! This process started back in March of 2025 when I was gone for the winter and she stayed in contact with me until we got a deal done on 10/8! It was a seamless process and I couldn’t be happier!

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.

Great customer service by Charles Brakebill and the entire Zeigler team. It sounds like they all work together very well and I was happy to see that. I bought a used Chevy but I'm happy to be part of the Subaru family.

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.

It was a very smooth experience, Nick Marzullo was extremely helpful - even off of the clock!

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 !

Their excellent service and support truly made me feel confident and well taken care of throughout the entire process. From the moment i arrived, everything was handled with professionalism and genuine care. It’s rare to find a place where you feel both valued and understood as a customer, but that’s exactly the experience i had here. Once again, thank you, Zee—your outstanding service truly stood out.

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!

I took my Audi in for an oil change, and the service I received was phenomenal! Blake McCarty went above to assure I had a great experience. Once my vehicle was done he walked me out and opened the door for me. Now that's top notch service. Thank you Blake for the best customer service ever! Keep up the good work.

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.

I recently bought a Subaru from Patrick at Subaru dealership in Orland Park. He was very informative very friendly and I would definitely refer him to anyone to buy a car.

Love my jeep. They have come a long way baby!! I am now a Jeep girl for life and recommend them highly. No matter the weather my Grand Cherokee gets me there in comfort and safety.

Jim and James father and son very professional duo I want to thank you both so much for working with me and being so present in your jobs. Thank you both so much.

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.

Real curtious and knowledgeable staff I would tell my friends and family about this car lot

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).

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.

Awesome service from Jose!!! Very patient and kind. Explained every detail. All dealerships need a Jose!

The turning radius is the best for the size of this suv. The brakes are quick to respond. The 4x4 is a must. The only downside is that they aren't all standard with a trailer hitch. Love the sunroof, the all leather interior.

This dealership is so friendly and they don’t hound you to buy a car like a lot of places. They take their time with you and explain things. They take care of their vehicles too. I purchased a 2017 Ford from them.

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

Triple M motors was incredibly helpful. I was able to get rid of my broken down piece of junk and trade it in for a newer model. Danny provided me with very useful information that made my decision easy.

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.

we bought 4 different vehicles in total from them, Frank and Jennifer are the best.

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.

Hands down the best Jeep ever.. would take it over the Santa Fe any day of the week.. there’s no comparison.. performance is excellent.. have 70,000 miles on a 2018 and a 2019.. ac went out on one but warranty covered it🙂🙂