Used Jeep Gladiator trucks for sale near Crestwood, IL under $100,000

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!

My Gladiator is 3 years old. Driving in Alaska and what a great vehicle. Starts every morning with no issues. Drives great in deep snow thanks to the ground clearance. The ride is stiff-it’s a Jeep.

I was a little skeptical about purchasing a vehicle I had not seen in person, the owner Michael was extremely helpful and reassured his words were honest, happy to say we are pleased with the purchase. Had this beauty shipped to Texas and it arrived in a timely manner. Definitely recommend!

We special ordered a Jeep Galdiato Rubicon in 2021 and loved it. Our only problem was it didn't leave much space in the garage. We decided to trade it for a special ordered Jeep Wrangle 4dr. RubiconX. This new vehicle left us with 34 more inches of space in our garage. We still have our 2021 Jeep GrandCherokee Trailhawk as our long trip vehicle. 2 never gave any problems accept with the Aux, battery after 3 years of own

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!

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!!

Best experience ever in buying a new car best salesmen Ernie and best finance manager Tom They made is so easy and fast and no run around

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.

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.

Excellent sales people! A truly great experience with extremely knowledgeable people. The auto was in magnificent condition, and the sales procedures were very well executed. It is a dealership that I will continue to purchase from and recommend!

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.

I had a great experience with them! They made the process very easy and even gave me a better rate than my own credit union, which I've been with for over five years. I highly recommend them to anyone looking for excellent service and competitive rates. Thank you!

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!

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.

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!

Alex was very professional ans I got to leave with my car very helpful go to him he will help you

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 !

Love this truck/Jeep! I moved from a SUV to this Gladiator and have never looked back! I have not found anything that I cannot do! If you have any sort of lift, have the fasteners checked every 30,000 miles. Just a FYI, I speak from experience.

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!!

Very good vehicles. It was great to work with the people at Chicago Auto Warehouse.

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.

I have been searching for a Saturn sky for about a year. I was fortunate that I found this dealership on the internet and was able to find exactly what I had been looking for. I was really apprehensive about buying a car sight unseen and from a stranger with the fraud schemes that happen all the time but I talked myself into it. The customer service was fantastic, the car is immaculate and everything they said it would be!! Thanks guys for restoring my faith in humanity. You are truly one of the good ones and I will recommend you to everyone.

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.

Excellent experience dealing with Eric. I purchased remote and from initial contact to after delivery questions he was responsive and helpful. I would purchase again from this dealer!

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.

We were so happy to have been helped by Elijah he was truly so patient with us as we were getting a bit nervous on not getting the vehicle of our choice. He was truly helpful all the way to the end. He was very informative about everything highly recommended him for any purchases at Dodge Ram. He's the man. Thank you Elijah you are truly the MVP hands down.

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.

Sam provided me with the best service experience , good prices, explained how things go in my car , I have zero experience with cars, he went out of his way to explain everything for me and made things clear

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!!

Always Our experience with Juam Carlos And Marino Dealer is excellent!!! We are happy with 5 new car!!! |||●●||| Thank you again!!!

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.

Made me feel like family as soon as I walked in very helpful and accommodating to my needs didn?t feel rushed at all great staff and location overall.

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".

JSON helped me out today t south oak and personally edge my vehicle thank you

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 cannot brag enough about the awesome service received on a recent car repair I have had… Starting with Jackie and all the way through. I was nothing but totally satisfied at how understanding,accommodating ,caring and patient all these employees were. If i could, I would rate these employees and their service 10 stars rather than five… Exceptional service is what I always receive. Thanks Bettenhausen for never disappointing. Always a smooth ride when dealing with Bettenhausen…

I am a old school jeep owner, what they have come up with in the Gladiator is a hit. The ride along with rugged styling and performance and a usable pickup bed is fantastic.