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*Estimated payments are calculated by Cars.com and are for informational purposes only. We’ve estimated your taxes based on your provided ZIP code. These estimates do not include title, registration fees, lien fees, or any other fees that may be imposed by a governmental agency in connection with the sale and financing of the vehicle. Other taxes may apply. They do not represent a financing offer or a guarantee of credit from the seller. Actual terms vary by lender.
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Used
Jeep trucks
for sale
near
Chicago, IL
- Down Payment
- $0
- Net trade-in value
- $0
- Months
- 72
- APR
- 7.0%
- Sales tax
- 0.0%
*Estimated payments are calculated by Cars.com and are for informational purposes only. We’ve estimated your taxes based on your provided ZIP code. These estimates do not include title, registration fees, lien fees, or any other fees that may be imposed by a governmental agency in connection with the sale and financing of the vehicle. Other taxes may apply. They do not represent a financing offer or a guarantee of credit from the seller. Actual terms vary by lender.
Used
2021 Jeep Wrangler Unlimited Sahara
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Used
2021 Jeep Gladiator Sport S
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Reviews
Great Truck/Jeep
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.
Used
2020 Jeep Gladiator Overland
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Reviews
Great customer service and a great car
I have to say I had excellent customer service, they help me with my finance, and my car, I love my car thank you so much happy customer 👍
Best vehicle I’ve ever owned. And I’ve owned many
Went to the dealership in August of 2020 to get a 2 door Willy. They did not have any and due to COVID did not know when they were getting any in. I had just purchased a grand Cherokee from same dealership about a year prior but needed a jeep wrangler as I previously owned one. They had a 2020 Jeep Gladiator sport on the showroom floor with a ton of extras (2 inch lift kit, all Fox shocks, coated bed liner, custom bed cover (hard shell), 34” all terrain tires, Matt black 18” wheels, led light bar mounted right in front of the front windshield, 2 led lights at front on either side, custom soundproofing on the inside hard shell top and I think the beefed up tow package but not sure. Within the first 2000 miles loaded a 35’ tv weighing 5800 pounds and headed out to Utah from Chicago driving through Colorado. The thing was phenomenal towing this heavy rv up and down the mountain pass on I 70. At a gas station some guy with a fifth wheel and a Ford F350 asked me what I was doing towing such a big rv with such a small truck. Kinda laughed. Saw him on the road later going up a mountain pass and blew right past him in my small truck. This truck has been nothing short of amazing. The dealership I purchased from is the best I’ve ever dealt with (Fields Chrysler/Jeep in Glenview, Il). They always have a loaner if needed. They are awesome. I bought in August of 2020 and today I have just shy of 70k miles on it and still running strong. I do not know why everyone says these things top off at 97 mph. I have gotten mine up to 110mph with a bit of room to spare. Gets to over a 100mph rather quickly. Maybe I just lucked out on a good one. I’ve read a lot of people complaining about a little water run off from the front door design. They are not wrong but you bought a freakin jeep, you’re not going to melt. Grow a set. Best vehicle I have ever owned. Best part with all the extras that came with it I got it for 49k with 15 miles on it. That same gladiator was there when I bought my grand Cherokee. I guess they were sick of it sitting on their showroom floor because back then it was listed for a tad over 60k.
Used
2023 Jeep Gladiator Overland
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Reviews
Good selecrion
Wide selection and no haggle are a plus over other dealerships. I like being able to see how many different makes and models. CarMax is the only place I will shop
Always go to Pilson auto, we always use the same
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!
Used
2021 Jeep Gladiator Willy's
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Reviews
Buy was a good experience
Mike Smith at CarMax was awesome very easy to deal with, very friendly, not pushy. He went out of his way to help us. I would recommend him to everyone needing to purchase a good used car.
mojave
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.
Used
2023 Jeep Gladiator Sport
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Reviews
Excellent and very friendly dealership
This is one of the largest CarMax that I've been to and they have quite a selection of cars. The salesperson was not pushy and were very friendly. The salesperson I worked with was Felicia and she was exceptionally great. I would highly recommend this dealership because of her superb customer service, knowledge of cars, and hospitality.
Jeep lifestyle
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!!
Used
2020 Jeep Gladiator Sport S
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Reviews
Good experience fast service
I had a good experience with Chris Price awesome sales man.. no pushy sales tactics.. he was honest and straight to the point.. I have bad credit.. and was turned down from alot of different dealers Marino, Hawk,Naperville and Shermans.. all said No.. but Carmax have me thre car I wanted wth super low miles.. Thanx Chris you a good guy 🤗
great jeep
own 2022 gladiator mojave for a year.its been perfect everyone loves it.its sarge green added added a rollbar ana a row of lights it really set it off.drove about 13000 miles in a year
Used
2021 Jeep Gladiator 80th Anniversary
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Reviews
A dealership you can trust
I was looking for a specific car that was at this CarMax. Problem was that I live in Minnesota, not Chicago and would have to traveling a great distance for a car I had not seen other than in pics, potentially risking wasting a great deal of time and money. I had to trust Jonathan, my salesman, to tell me the condition of the car where the pics could not. He was completely honest and the car was exactly what he said it was. Between Jonathan and Adam, the sales manager i was able to close the deal and drive back to home within an hour. I am completely pleased with the car and 100% satisfied with the dealership. I guess you can trust a car dealership. I did and they did not let me down. Thanks guys.
Definitely a fan!
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!!
Used
2020 Jeep Gladiator Rubicon
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Great place for an affordable Used Car
I had a great experience car shopping at CDJR. Brian even threw in two free oil changes and details when we closed and made a deal. Looking forward to receiving the title to my new car.
2020 Jeep Gladiator Sport
My Gladiator is lifted and has a convertible top. I can use it for formal purposes and dirty job purposes. It’s a beach car too. I even tow it behind my RV. I Love this vehicle and never thought I would. I took my wife’s Wrangler in for service and got mine as a loaner. It was God’s plan.
Used
2021 Jeep Gladiator Overland
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Reviews
Service
As always Jennifer is so helpful and friendly. Keeps me posted on time frame. This was routine oil change.Service manager Mike J. is great to work with
MOHAVE ride makes for good daily driver
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.
Used
2021 Jeep Gladiator Sport
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Reviews
Efficient service
The conversations I had with the salesman where Outstanding. In fact, he worked with me on my day off. It was a smooth process throughout. From the negotiation of price, financing to the end result delivery from IL to MO. Kudos to Steve Foley!!
Buy! Best of the Best!
The best by far mid size truck you can buy! Built better than any truck you will find on the market, hands down an easy choice!!!
Used
2021 Jeep Gladiator Willy's
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Reviews
Amazing
Mike R was amazing. He even traveled to Chicago to bring our car to a different locations so we could see it. I would highly recommend this location.
Used
2021 Jeep Gladiator Willy's
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Reviews
Mr Marcel Potvin To me CarMax is number one in car
I could not get a decent car any were CarMax put me back into the drivers seat i will recommend CarMax to anyone Andrea and his team in Tinley Park are truly number one in car sales . Marcel Potvin.
Used
2020 Jeep Gladiator Mojave
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Reviews
I initially checked to see if the SUV I found on cars.
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!
best truck ever
Upgraded from a 2 door JK. What a difference. Way nicer and much more comfortable as a daily driver. This truck is a beast. Never worry about going off road. Did add a Winch just to be safe.
Used
2021 Jeep Gladiator Rubicon
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Reviews
Great dealership
The reviews don’t lie. Just bought my daughter her first car. No pressure, everyone was nice and probably the quickest ( and still not quick enough) time I’ve spent buying a car.
Used
2021 Jeep Gladiator Mojave
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Used
2022 Jeep Gladiator Overland
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Reviews
Purchase cars thier away happy with staff and serv
Bought 4 cars thier in 10 years they our best in sales and service staff the best service is out standing they care alot for customers
What’s Not to Like
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.
Used
2023 Jeep Gladiator Sport
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Reviews
Ryan Paul was outstanding!
Ryan Paul was outstanding! Smooth purchase buying a Q3! He was so personable and made my experience wonderful. He’s funny too. He knew all the answers to my questions as well. If you are in search of a car, ask for him! He made it a truly great experience for me. Thanks! Sid was great too. and shout out Robert:)
Must Love The Jeep Experience
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".
Jeep Certified
2021 Jeep Gladiator Overland
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Reviews
ABDUL was VERY helpful to us within moments of us walking
ABDUL was VERY helpful to us within moments of us walking through the doors at 9:00 a.m. Saturday morning. He facilitated our selection process from our initial inquiry to our final selection. He exhibited good salesmanship, active listening, leaning in, gaining rapport, relevant & meaningful story-telling, and carefully wove the common thread of love for family into the selling process...we even found common ground about cultural things that we found funny...The skills he exhibited and values we shared seem to be disappearing in this new economy. We LOVED Lewis. Lewis knows every aspect of financing inside and out. He's so smooth. He respects a "NO" then remains conversational and low-key until he gets to "YES". Smooth! Top Performer's Sales Training at its best! We connected immediately and beyond just an occasional LOL, we Laughed Out Loud - LOUD and OFTEN...By the time we left, we were tired, hungry, but IMMENSELY pleased with all of the contractual guarantees, servicing/warranty explanations, being financed by the company of our choice - and our friendship with Lewis. You'll LOVE his iconic signature!
Jeep Certified
2023 Jeep Gladiator Sport
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Reviews
Elvir and Matt did a great job and I was pleased with the
Elvir and Matt did a great job and I was pleased with the attention, negotiation and the car I got.
23 Jeep Gladiator Sport
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! 🤪
Used
2021 Jeep Gladiator Sport
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Reviews
Such a wonderful seamless experience.
Such a wonderful seamless experience. John Nanni was a gentleman to work with. No hard sell! Just a smooth engagement. First rate!!!
Jeep Certified
2021 Jeep Gladiator Overland
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Reviews
Excellent sales experience with Javier and the rest of
Excellent sales experience with Javier and the rest of the staff at Castle jeep. He made it easy and quick. He didn’t even try to sell me LoJack. I would recommend this dealership.
*Estimated payments are calculated by Cars.com and are for informational purposes only. We’ve estimated your taxes based on your provided ZIP code. These estimates do not include title, registration fees, lien fees, or any other fees that may be imposed by a governmental agency in connection with the sale and financing of the vehicle. Other taxes may apply. They do not represent a financing offer or a guarantee of credit from the seller. Actual terms vary by lender.