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Used
Jeep Gladiator trucks
for sale
near
Winnetka, IL
under $40,000
- 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.
**Your Saved Vehicles list will be shared along with your contact information when you submit a vehicle request to a dealership. To opt out of this sharing, please view your options on Cars.com Privacy Notice.






Used
2021 Jeep Gladiator Overland
Vehicle information
Features
Reviews
I was contacted immediately by Tom N, who very helpful
I was contacted immediately by Tom N, who very helpful and eager to assist us with our search
We special ordered a Jeep Galdiato Rubicon in 2021 and
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






Used
2022 Jeep Gladiator Rubicon






Used
2023 Jeep Gladiator Willys 4x4
Vehicle information
Features
Reviews
Great dealership!
Great vehicles! Great service! Highly recommend this dealership who’s looking for a hassle free buy and very transparent paper work! Thank you baha auto group!
MOST importantly it is a JEEP.
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!






Used
2020 Jeep Gladiator Rubicon
Vehicle information
Features
Reviews
Great Experience
I purchased a car in early April and I had a pleasant experience. Mike the owner/manager of the facility ensured that any concerns that I may have had were addressed promptly. I’ll for sure look to purchase here in the future.
my grandmother sadly traded in this gladiator i wish she
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.






Used
2021 Jeep Gladiator Rubicon
Vehicle information
Features
Reviews
We actually traveled four hours to this Chicago used car
We actually traveled four hours to this Chicago used car dealership that listed a lot of used model X's, drove a couple, then found out that they will personally inspect a car and give us a high-quality video walk around and deliver to us for $350 [chicago to 49417]. Nader was very helpful and patient. So we went home and kept checking online until that dealership listed the car with all the options we wanted, then got videos via txt, called back and asked some basic questions, then bought and had it delivered. They also helped us navigate the intricacies of an interstate purchase. We also learned that model X's move quickly, Driven Auto dozens of cars per week if not more, so when you see it you better pull the trigger quickly
Have driven Jeeps in the military and loved the
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!!






Vehicle information
Features
Reviews
I purchased a 2008 CL 550 that I absolutely love.
I purchased a 2008 CL 550 that I absolutely love. It drives almost like it’s brand new despite being 18 years old. My salesman Chris went above and beyond with getting me in this car and even fixed the air conditioner on another vehicle I drove there to buy this car! I’ve never had that happen before. My future car purchases will be with him and this dealership!
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
2021 Jeep Gladiator High Altitude 4X4
Vehicle information
Features
Reviews
Larry is extremely helpful and patient
Highly recommend Larry Williams at Toyota of Lincolnwood. He's patient, caring, and knows his stuff. He was very helpful in assisting us in getting a specific car we wanted. Great at explaining all the car's perks too.
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
2022 Jeep Gladiator Overland
Vehicle information
Features
Reviews
Great service.
Great service. The service department was courteous and friendly. My car was serviced and ready to go in a reasonable amount of time. I was very satisfied.
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 Willys 4x4
Vehicle information
Features
Reviews
I am going to this dealership for last 10 years.
I am going to this dealership for last 10 years. Amazing staff and services. Always available to drop you off home if needed.
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
2020 Jeep Gladiator Rubicon
Vehicle information
Features
Reviews
Best experience purchasing a vehicle.
My husband went into the dealership this afternoon and worked with a member of the sales team named Victor. He was able to work with our credit and our trade in to get us into a reliable vehicle that we could afford. He was thorough and efficient and we were well taken care of. We appreciate his help and couldn't be happier with the experience.
my grandmother sadly traded in this gladiator i wish she
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.






Used
2021 Jeep Gladiator Overland
Vehicle information
Features
Reviews
Great service!
Went for a scheduled oil change. Waited about 1 hour, which is pretty normal. Was treated with respectful & courteous service from the service adviser. Have been going to this dealership for a long time. I would recommend them for your service needs.
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 High Altitude 4X4
Vehicle information
Features
Reviews
I was in the market for a used rubicon wrangler, Sherman
I was in the market for a used rubicon wrangler, Sherman dodge had the vehicle I wanted. Upon my arrival I was greeted by Jesse W and from the time I arrived to the time I left in my new vehicle he was very attentive to my every need! I felt like I left with an amazing deal!






Jeep Certified
2021 Jeep Gladiator Rubicon
Vehicle information
Features
Reviews
Svet was amazing omg he helped me soooo much he was nice
Svet was amazing omg he helped me soooo much he was nice patient and he got me what was affordable for my daughter and I this man is definitely an angel and he’s very professional he’s the best there is






Used
2023 Jeep Gladiator Sport S
Vehicle information
Features
Reviews
Quick communication and smooth process.
Quick communication and smooth process. Ov Perez was very professional, helpful salesman who made the sale a great experience.
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
2021 Jeep Gladiator Willy's
Vehicle information
Features
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






Used
2022 Jeep Gladiator Sport S
Vehicle information
Features
Reviews
Yesterday I purchased a car by phone for the first time.
Yesterday I purchased a car by phone for the first time. As a senior citizen I sold my car on the 9th of March thinking I would get totally travel by taxi or Uber or Lyft but I under estimated the value of getting up and going when you like. The team at CarMax from beginning to directions to the highway were the very best. Each and every member made me feel valued as a customer. And feel like they were treating me like they would their family members. You could not ask for more than that. Bj
Great vehicle poor local warranty service
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.






Used
2021 Jeep Gladiator Sport S
Vehicle information
Features
Reviews
The sales Mando is nice and patient.
The sales Mando is nice and patient. The whole experience is speedy and pleasant. I was able to shop for the car I want with minimum effort.






Used
2021 Jeep Gladiator Sport S
Vehicle information
Features
Reviews
just purchased a 2021 Mercedes Great experience ask for
just purchased a 2021 Mercedes Great experience ask for Ryan he will take care of you!






Used
2021 Jeep Gladiator Willys 4x4
Vehicle information
Features
Reviews
96 caprice
I purchased a 96 Caprice from this dealer.....buying experience was top notch. They answered all of my many questions about the car, negotiated price with me and had the car delivered in record time. The vehicle arrived in an enclosed trailer, was clean and ran perfectly. There were no issues with the car that I found. Normal wear and tear for a 21 year old car but very clean and taken care of. All systems worked as advertised. Top notch vehicle and dealership






Used
2021 Jeep Gladiator Overland
Vehicle information
Features
Reviews
EXOTIC MOTORS HAS HANDS DOWN THE MOST EXOTIC AUTO
EXOTIC MOTORS HAS HANDS DOWN THE MOST EXOTIC AUTO COLLECTION I HAVE EVER SEEN IN ONE LOCATION. I FOUND MY DREAM CAR A 2017 MERCEDES-BENZ AMG GLE 63. THE SALES AND PROCESS WAS THE SMOOTHEST I HAVE EVER EXPERIENCED. DONT GO ANYWHERE ELSE EXOTIC MOTORS IS YOUR ONE STOP SHOP WITH TOP QUALITY VEHICLES AND SERVICES. THE BEST IN MY BOOK!. IM DISABLED AND THE RIDE IS A BIT HARD ON MY SPINE BUT I HAVE NO DOUBT THEY WILL RESOLVE THE MINOR ISSUE TO A AMAZING TRUCK, ILL KEEP UZ POSTED WITH AN UPDATE. DENNIS IS A GREAT SALES MANAGER AND SALEEM IS JUST A SOLID BUSINESS OWNER WITH THE BEST INTEGRITY!. THANKS GUYS! ANDRE RODRIGUEZ.






Used
2023 Jeep Gladiator Sport S
Vehicle information
Features
Reviews
Great experience, quick to set up, check in and out and
Great experience, quick to set up, check in and out and everything was quoted with pricing. Time was appropriate for the amount of work done
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 Gladiator prices by year
Model year | Prices from | Deals |
---|---|---|
2025 Jeep Gladiator | $36,357 | |
2021 Jeep Gladiator | $27,500 | 14 Good deals |
*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.
**Your Saved Vehicles list will be shared along with your contact information when you submit a vehicle request to a dealership. To opt out of this sharing, please view your options on Cars.com Privacy Notice.
Used Jeep Gladiator by price
Compare the Jeep Gladiator
Jeep Gladiator under $40,000 by city
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Jeep Gladiator under $40,000 in Winnetka, IL
13 Great Deals out of 44 listings starting at $24,980
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Jeep Gladiator under $40,000 in Kenilworth, IL
15 Great Deals out of 46 listings starting at $24,980
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Jeep Gladiator under $40,000 in Northfield, IL
15 Great Deals out of 50 listings starting at $24,980
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Jeep Gladiator under $40,000 in Wilmette, IL
15 Great Deals out of 46 listings starting at $24,980
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Jeep Gladiator under $40,000 in Glencoe, IL
14 Great Deals out of 47 listings starting at $24,980
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Jeep Gladiator under $40,000 in Glenview, IL
17 Great Deals out of 55 listings starting at $24,980
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Jeep Gladiator under $40,000 in Evanston, IL
15 Great Deals out of 47 listings starting at $24,980
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Jeep Gladiator under $40,000 in Skokie, IL
17 Great Deals out of 52 listings starting at $24,980
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Jeep Gladiator under $40,000 in Northbrook, IL
15 Great Deals out of 50 listings starting at $24,980
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Jeep Gladiator under $40,000 in Morton Grove, IL
17 Great Deals out of 56 listings starting at $24,980
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Jeep Gladiator under $40,000 in Highland Park, IL
11 Great Deals out of 45 listings starting at $24,980
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Jeep Gladiator under $40,000 in Niles, IL
18 Great Deals out of 60 listings starting at $24,980
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This vehicle is currently in high demand given its competitive price, desirable features, and overall condition, and may have a higher chance of selling quickly.
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