Used Jeep Gladiator trucks for sale near Merrillville, IN under $100,000

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.

It’s a Jeep, so people who buy this understand what it’s all about, great off road performance, reliable and fun to drive. The Gladiator is unique because it’s a pickup and gives you more flexibility on abilities to carry more, but doesn’t hamper performance in any way, also, priced well compared to similar vehicles.

They went 400 miles to get my van couldn?t ask for a better experience. The best Ford dealer in the area and one of the best dealerships of any kind. Ask for Tin Heineken.

Reliable and great looking truck! Love the way it rides and how many options they have to customize this great mid size vehicle. Love the color options

I want to thank Kristen for being so AWESOME! He professionalism was so much appreciated throughout my buying experience. She continued to reach out and help/support me in anything I needed after my purchase was made. Thank you so much Kristen. Keep up the good work!

my grandmother sadly traded in this gladiator i wish she would have kept it . It is very comfortable,reliable,it look great on the outside,it has enough power,and its value is very good.

The work was done well and quicker than I thought. I've come rely on their service department and have been their customer for many years

Have driven Jeeps in the military and loved the performance and easy maintenance. Have 2 Jeeps now and looking to replace one of my Jeep with another one. Love Jeeps!!

I can always count on my service needs being met. Quick Lane is convenient. My last service Was completed on time and corrected.

MOST importantly it is a JEEP. If you want a luxury vehicle, buy one, if you want a full-size truck, buy one, if you want a sports car, buy one, the Jeep Gladiator is none of these. It is designed to be a mid-sized pick-up yet still be a Jeep, it does this PERFECTLY. I have owned 9 Jeeps over the years, as early as 1978 up through 2006; the Jeeps today are full of more amenities and comfort than they ever have been in history. I have 2 Gladiators; a '23 Mojave, and a '23 Diesel Overland, both of them are INCREDIBLE vehicles on and off road, and MORE than fit the bill for a light duty pick-up, superseding most others on the market, and I am even comparing to any of the 5 Tacoma's I have owned. If you are in the market for a light duty pick-up, you can't beat it; whether it is a loaded up graded model, or even the base model, it is still a truck with 4WD, straight axles, and still available with a manual transmission. VERY happy with both of mine!

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 have a jeep gladiator mojave, 2021, great vehicle , the best i have ever owned, great for offroading and the suspension is great, designed for higher speed offroading and it does a great jjob at this and just regular off roading. also fun just to drive around town. Highly recommend this vehicle, i also love the xtras, led lights, safety features, (blind spot and ADC, etc), aux swithes . This just a great vehicle.

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.

I bought my 2021 Overland new. I love it!!! It is fun to drive. Handles well in the snow. This is a well made vehicle. I love the leather seating. The best heated seats and steering wheel I have owned. I’m definitely a fan!!

Always go to Pilson auto, we always use the same salesman. Always have a good experience! The salesman always answers calls and texts even if he is not at work! Everyone there has always been extremely friendly and helpful!

This dealership is amazing! No high pressure sales tactics, no last minute add-ons to the price. Great follow up after purchase to ensure we were completely satisfied with our purchase. Service went above and beyond expectations.

Mojave trim gives a smooth ride. A big improvement over the 2012 Rubicon Unlimited that I had. 17-18 mpg around suburbs and 20-21 on trips. At 13,000 miles no reliability issues. 8-Speed transmission coupled with the 3.6 v6 works well. Great in SNOW. Recommend the AWD optional transfer case.

The team was great to with with and helped make the process of cutting a car from across the country as smooth as possible. Thanks Jonathan!

my grandmother sadly traded in this gladiator i wish she would have kept it . It is very comfortable,reliable,it look great on the outside,it has enough power,and its value is very good.

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!

This is a.rock solid vehicle that defines “utility” better than all the rest. You have tons of ways to configure the vehicle every day. Open air roof, doors off, entire top off, pick-up truck uses, off roading, climbing, travel, snowshoeing, skiing, snow driving, trails and dirt roads, hiking, carry bed loads, trailering, ATVs, etc, etc, etc. No way to ever find it boring. Plus, the extra bonus of the culture, friendliness, the wave, jeep groups, and the way it promotes and nurtures getting outdoors and getting active. No issues. Alpine stereo is great. Nav is great. Heat is great. comfort great, carrying fun loads great, towing to 4K lbs great. No complaints.

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

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.

This is my 3rd Gladiator, I really enjoy the Jeep lifestyle, the Gladiator has been a great addition to my family and we have a ton of fun with it. It’s very versatile we use it for pulling our boat and Travel trailer and for everything else!!

Gone are the days of driving to the dealership to have your oil changed. I love that Webb Ford came to get my vehicle, showed me where they were en route, sent me texts where they were in the process, and returned my vehicle quickly. Absolutely worth it to me in my busy schedule. Awesome place.

Ethical, principled, honest, trustworthy, fair, and responsible — not words you usually associate with a used car dealership, but they perfectly describe owner Mark and manager Brion. When I purchased my 2020 Mercedes GLA 250 (now affectionately known as “Duchess” — because who doesn’t name their car?), they made the entire experience hassle-free and enjoyable. They went above and beyond to ensure my car was in excellent condition and worked with me promptly on any concerns. I highly recommend this dealership to anyone looking for a reliable car and a team that truly stands behind their product.

Ecodiesel gladiator is fun to drive and getting good MPG. My second gladiator and no issues. Jeeps aren't for everyone as they are boxy, heavy, noisy in cab at high speeds and not as luxurious as a Lexus. But these things are tanks with body on frame build, Dana 44 axles, real transfer case and mega offroad capability. Plus its easy to modify suspension and its a "jeep thing".

I think my 2022 Gladiator is one of the top vehicles I have owned The only drawback is the lack of warranty service from my local Jeep dealer.

With the prices of the Gladiator coming way down (because of incentives), it made it an affordable choice. Black on Black, with a tone of options. I love it, and most importantly so does my wife! 🤪

I have 84,000 miles. I don’t hit rod it. I keep it below 2500 rpm unless a must pass happens (rarely). Zero issues with transmission brakes electronics heat or AC. Overland model. It has been a wonderful rig with 19 to 25 mpg. I’m 64 and hoping this and my XJ are my last rides. Both rigs are exceptional. I had a scrambler and loved it, had to have the Gladiator and my 2020 has been far better than expected !

Brian Muller helped put me in the perfect vehicle with the right budget! needed something reliable for me and my kids and he went above and beyond. i feel very safe and happy with my vehicle, my kids couldn’t be any more happier riding around in a newer and safe vehicle. I would definitely recommend Brian to all my friends and colleagues. Thanks again!!

Great vehicle for enjoying the outdoors in being able to explore new places other vehicles could not go. Looks like a vehicle that can take you into areas safely.

Good service , service man was kool … easy process . Good vending machines too . Glad I chose this dealership