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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 Willys 4x4
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Reviews
Didn't buy anything but they were on their game.
Didn't buy anything but they were on their game. Willing to do anything. Will keep them in mind in the future.
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
2020 Jeep Gladiator Overland
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Reviews
Oil change, tire rotation
Good service, my car was not stolen from the dealer service center so that to me is a win :) Edgar was very professional and the waiting area was clean.
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
2022 Jeep Gladiator Rubicon
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Reviews
Great car buying experience with Jacob Gonzalez and his
Great car buying experience with Jacob Gonzalez and his sales manager George Stratikis. I would recommend any in the market for an Acura to visit McGrath
My Gladiator is 3 years old.
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.






Used
2022 Jeep Gladiator Rubicon
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Reviews
Everyone i dealt with at the dealership was very
Everyone i dealt with at the dealership was very welcoming. They were also quick and efficient getting me into my new vehicle.
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 Overland
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Reviews
Alexander Lopez was great to work with, hopefully he sent
Alexander Lopez was great to work with, hopefully he sent that cup and shirt. Wonderful experience.
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
2023 Jeep Gladiator High Altitude 4x4
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Features
Reviews
Abigail was great to work with!
Abigail was great to work with! She was friendly and very thorough when showing us all the options. Sari in finance was very patient and made sure we fully understood every step before proceeding. It gave us peace of mind knowing we were working with people who genuinely care. Thank you to the Joe, Abigail, Mostafa, Sari and Daniel. We will definitely be recommending Continental Toyota to anyone in the market for a car.
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 Sport S
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Reviews
Had a problem with the service department on Saturday
Had a problem with the service department on Saturday when price at payment time was more then discussed. Left dealer pissed off and called when I got home with a cooler head. Nothing was accomplished so I wrote a review that was seen by upper management. Saturday afternoon a gentleman named Mark called to discuss the issue with me. After talking in order to keep me happy and being a returning customer he first had offered his apology for the misunderstanding then refunded the entire service charge price to me. This showed me they're a stand-up dealership. The icing on the cake was the owner Dave called me on Sunday to apologize and assure me he was behind the total refund. Sherman in Skokie a place ypu can feel your needs will be addressed no matter what they are. I will be back in the future. Thanks again Mark and David!
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!!






Used
2023 Jeep Gladiator Overland
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Features
Reviews
Made me feel like family as soon as I walked in very
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.
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
2022 Jeep Gladiator Willys
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Reviews
Excellent service and execution from Jeff Williams and
Excellent service and execution from Jeff Williams and the whole autobarn Mazda team in Evanston
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
2020 Jeep Gladiator Overland
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Reviews
Perfect Vehicle, great salesperson!
My sales person Alex Valdez was great! I thought he would give up on me because I was very picky and expected alot. I had resigned myself to keeping my current car, but then he found me the perfect vehicle and I love it! All in all it was a pleasant experience and I highly recommend McGrath Honda/Elgin. Just ask for Alex Valdez and he will work hard to find you what you want!
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
2023 Jeep Gladiator High Altitude 4x4
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Reviews
These guys are awesome.
These guys are awesome. From Bloomington, we drove and made a deal. A big shout out to Steve, a really knowledgeable sales consultant especially about Nissan cars.
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".






Used
2021 Jeep Gladiator Mojave 4X4
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Reviews
It was a pleasure working with Sam at Woody Buick GMC in
It was a pleasure working with Sam at Woody Buick GMC in Gurnee. The whole staff is friendly and professional.
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
2022 Jeep Gladiator Willys 4x4
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Reviews
I purchase a 2019 Qx60 my experience was very very good
I purchase a 2019 Qx60 my experience was very very good sale person Thomas pates did a wonderful job to get me in this car everyone was helpful I will purchase another vehicle from there I am from Milwaukee thanks carwise
Explore New Areas
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.






Used
2023 Jeep Gladiator High Altitude 4x4
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Reviews
We've worked with Tony before & he is very
We've worked with Tony before & he is very knowledgeable & knows just what we like.
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 Rubicon
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Reviews
I recently purchased my Audi with Dexter Gordon.
I recently purchased my Audi with Dexter Gordon. From start to finish, Dexter was wonderful to interact with. He was helpful, professional and knowledgeable. If you want to interact with a non-pushy sales person who actually cares about choosing the right car for your lifestyle and budget, Dexter is your guy. He was also incredibly patient with me as I was quite undecided. But he gave me my space and time to decide as I am the type of person that needs to internalize options before pulling the trigger. To my surprise, he did not push me to purchase same day which I appreciated as I don't like to be pressured; purchasing a car is a huge decision. He was also transparent in his interactions with me. Thank you, Dexter for your patience and guidance throughout the entire process. I will definitely recommend you to friends and family since my experience was so pleasant.
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 Overland
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Reviews
Thank you Mike and Jonny for helping my husband get his
Thank you Mike and Jonny for helping my husband get his new truck!! Mike thank you for your great service and Jonny for wrapping it up to get on the rode!! Everybody else was all smiles and very welcoming...
I have 84,000 miles.
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 !






Used
2020 Jeep Gladiator Rubicon
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Reviews
Rich was great - very easy process to purchase my new
Rich was great - very easy process to purchase my new Ford Expedition. Thanks for everything!
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 Sport S
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Reviews
I had been hunting for a clean Tesla Model Y for weeks
I had been hunting for a clean Tesla Model Y for weeks and finally connected with Eddie Baker. He made everything easy from the start, explained the rebate program clearly, and even helped me line up financing. I drove away in my 2021 Model Y and couldn’t be happier. Eddie really knows his stuff and made me feel comfortable the whole way through.
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
2020 Jeep Gladiator Sport S
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Reviews
Just picked up a new 2025 Explorer at Packey Webb.
Just picked up a new 2025 Explorer at Packey Webb. It was a smooth and professional purchase process. Ernie and Kevin took great care of me. You bet I?ll be back! I am really impressed with the recent changes Ford made to the Explorer.






Used
2021 Jeep Gladiator Sport S
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Reviews
Bought my wife a trailblazer from Rheya and she was
Bought my wife a trailblazer from Rheya and she was amazing. Very easy experience and she was incredibly helpful. Would 100% recommend her to anyone in the market!!
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.
Jeep Gladiator prices by year
Model year | Prices from | Deals |
---|---|---|
2025 Jeep Gladiator | $36,357 | |
2021 Jeep Gladiator | $27,500 | 5 Great deals |
About the Jeep Gladiator
How much does the Jeep Gladiator cost?
The Jeep Gladiator price depends on several factors, including the trim level, optional features, mileage, vehicle history and location. The nationwide average price for the Gladiator is $35,356, with pricing starting at $13,980.
What is the MPG of the Jeep Gladiator?
The Jeep Gladiator with traditional internal combustion engine offers up to 17 MPG city and 22 MPG highway for a combined rating of 19 MPG.
These figures are based on EPA mileage ratings and are for comparison purposes only. The actual mileage will vary depending on the selected vehicle model year, trim, driving conditions, driving habits, vehicle maintenance, and other factors.
What are some similar vehicles and competitors of the Jeep Gladiator?
The Jeep Gladiator compares to and/or competes against the following vehicles:
What trim levels are available for the Jeep Gladiator?
The Jeep Gladiator is available in the following trim levels:
What model years are available for the Jeep Gladiator?
Available model years for Jeep Gladiator inventory range from 2020 to 2025.
*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
-
Jeep Gladiator under $40,000 in Kenilworth, IL
17 Great Deals out of 45 listings starting at $24,980
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Jeep Gladiator under $40,000 in Northfield, IL
17 Great Deals out of 49 listings starting at $24,980
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Jeep Gladiator under $40,000 in Wilmette, IL
17 Great Deals out of 45 listings starting at $24,980
-
Jeep Gladiator under $40,000 in Glencoe, IL
16 Great Deals out of 46 listings starting at $24,980
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Jeep Gladiator under $40,000 in Glenview, IL
19 Great Deals out of 54 listings starting at $24,980
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Jeep Gladiator under $40,000 in Evanston, IL
17 Great Deals out of 46 listings starting at $24,980
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Jeep Gladiator under $40,000 in Skokie, IL
19 Great Deals out of 51 listings starting at $24,980
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Jeep Gladiator under $40,000 in Northbrook, IL
17 Great Deals out of 49 listings starting at $24,980
-
Jeep Gladiator under $40,000 in Morton Grove, IL
19 Great Deals out of 55 listings starting at $24,980
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Jeep Gladiator under $40,000 in Highland Park, IL
13 Great Deals out of 45 listings starting at $24,980
-
Jeep Gladiator under $40,000 in Niles, IL
20 Great Deals out of 59 listings starting at $24,980
-
Jeep Gladiator under $40,000 in Deerfield, IL
16 Great Deals out of 51 listings starting at $24,980
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