Used Jeep Gladiator for Sale near Chicago, IL
CarGurus recommends the 2021 Jeep Gladiator
Summary
- With 6,050 currently listed for sale on CarGurus and an average price of $32,429.50, 34.5% of 2021 Jeep Gladiators for sale on CarGurus are rated as good or great deals.
- Favorably reviewed: Owners rated the 2021 Jeep Gladiator 4.8 / 5 stars and CarGurus experts gave it an 7.2 / 10.
- 85% of 2021 Gladiator models on CarGurus are accident free.
- The 2021 Jeep Gladiator introduced a diesel engine option, enhancing towing performance with 442 lb-ft of torque for improved capability.
Why it stands out
The Jeep Gladiator excels in providing a unique blend of off-road capability and open-air driving experiences, setting it apart from other midsize pickups. Its removable top and doors, along with a robust aftermarket support, allow for extensive personalization and adventure-ready versatility. Additionally, the Gladiator's impressive towing capacity and Trail Rated badge underscore its ability to handle both work and play with confidence.
Other model years to consider
The 2020 Jeep Gladiator emerges as a highly suitable alternative due to its strong user rating of 4.7/5 and an average price that is more affordable compared to newer models, making it an attractive option for budget-conscious buyers. Additionally, with 34% of listings classified as good or great deals, there is ample inventory available, enhancing the likelihood of finding a well-priced vehicle. The 2022 model also presents a moderately suitable choice; while slightly pricier at $33,826.65 and with a user rating of 4.4/5, it still offers a solid selection with 35% good/great deals available on the market.
Model years to approach with caution
Based on the latest market metrics, the 2024 Jeep Gladiator stands out as the most suitable option, featuring a competitive average price and a relatively favorable expert rating despite a significant percentage of buyers not perceiving it as a great deal. The 2025 model, while slightly more expensive and with a lower expert rating, reflects moderate customer satisfaction but faces similar deal perceptions in the marketplace. Conversely, the 2026 model appears to be less optimal for buyers due to its high percentage of unfavorable deals, suggesting that potential purchasers should carefully consider their options when looking at this year's offerings.
These recommendations are based on CarGurus' proprietary market data from November 18, 2025, CarGurus experts' opinions, and generative AI.
4.8 Overall rating
(168 reviews)Customers say
The Jeep Gladiator impresses owners with its off-road capabilities, rugged design, and versatile performance. Many drivers enjoy its powerful feel and smooth ride, appreciating the blend of technology with a tough exterior. However, there are common criticisms regarding the interior space being smaller than expected, the price point relative to features, and concerns about fuel efficiency and comfort. Overall, it's celebrated as a unique vehicle that stands out, especially for those who value ruggedness and off-road performance.
AI generated from the text of customer reviews.
What people say
This truck is absolutely beautiful inside and out. It’s a surprisingly quiet ride. I love all the bells and whistles the rubicon has to offer. I wouldn’t change a thing.
Great truck, very roomy inside and it’s fun to drive it, I just love it!
Wonderful vehicle. This is my second one. Discounts off of MSRP were too good to pass up. Very capable off-road with the ability to be upfitted with over-landing gear.
This is the third day of ownership. So far so good. This is my second Jeep. The first one was a Jeep Wrangler Rubicon which I had for nine years. I was looking for a truck but test drove a Mojave. I was pleasantly surprised at how much they have improved and how much I fun it was to drive. The suspension is so smooth and it’s much quieter than my old Jeep. I like the mix of truck and Jeep.
Really love the smooth ride and the way it drives much better than my previous Jeep
Jeep Gladiator FAQs
How much does the Jeep Gladiator cost in Chicago, IL?
The average Jeep Gladiator costs about $33,922.66. The average price has decreased by -1.7% since last year. The 9187 for sale near Chicago, IL on CarGurus, range from $14,480 to $199,995 in price.
Is the Jeep Gladiator a good car?
CarGurus experts gave the 2025 Jeep Gladiator an overall rating of 5.3/10 and Jeep Gladiator owners have rated the vehicle a 4.7/5 stars on average. If a vehicle has both strong expert and owner reviews, you can feel confident in its quality. If either expert reviews, owner reviews, or both are spotty, you might want to do some research to figure out where the car falls short.
How many Jeep Gladiator vehicles in Chicago, IL have no reported accidents or damage?
8067 out of 9187 for sale near Chicago, IL have no reported accidents or damage.
Is the Jeep Gladiator safe?
CarGurus experts gave the 2025 Jeep Gladiator a safety rating of 3/10.
What fuel types are available?
Diesel, Gasoline engines are available.
-
Small Trucks for Sale in Chicago IL
-
Shop cars from Fast & Furious 9 for sale in Chicago IL
-
Jeep SUVs & Crossovers for Sale near Chicago IL
-
American Made Trucks For Sale in Chicago IL
-
Best Pickup Trucks For Sale in Chicago IL
-
Used Jeep Gladiator for Sale with Low Mileage
-
Used Pickup Trucks for Sale with Low Mileage
-
All Used Cars
-
Manual Transmission Cars
-
Luxury Cars
-
Cars with Red Interior
-
Cheap Manual Cars
-
Hybrid Cars
-
Sports Cars
-
Electric SUVs
-
Cheap Trucks
-
Small Cars
-
Third Row SUVs
-
Three Quarter Ton Trucks
-
Lifted Trucks
-
Manual Transmission Trucks
-
Diesel Trucks
-
Hybrid SUVs
-
Dually Trucks
-
One Ton Trucks
-
Cheap SUVs
-
Lifted Ford Trucks
-
4x4 Trucks
-
Work Trucks
-
AWD SUVs
-
Ford Trucks
-
Chevrolet Trucks
-
Toyota Trucks
-
Trucks Under $10,000
-
Cars Under $15,000
-
Sports Cars Under $20,000
-
Trucks Under $20,000
-
Used Sedans for Sale with Low Mileage
-
Used SUVs / Crossovers for Sale with Low Mileage
-
Used Hatchbacks for Sale with Low Mileage
-
Used Convertibles for Sale with Low Mileage
-
Used Vans for Sale with Low Mileage
-
Used Minivans for Sale with Low Mileage
-
Used Pickup Trucks for Sale with Low Mileage
-
Used Coupes for Sale with Low Mileage
-
Used Wagons for Sale with Low Mileage