Used 2021 Jeep Gladiator for Sale near Chicago, IL
408 results
CarGurus Analysis:
2021 Jeep Gladiator
With 410 currently listed for sale near Chicago, IL and an average price of $31,450.00, 30.2% of 2021 Jeep Gladiators for sale on CarGurus are rated as good or great deals.
Favorably reviewed: Owners rated the 2021 Jeep Gladiator 5 / 5 stars.
96.6% of 2021 Gladiator models on CarGurus are accident free.
The 2021 Jeep Gladiator returns with a new turbo-diesel engine option, enhancing its off-road capabilities and overall performance while retaining its rugged design.
CarGurus Analysis: 2021 Jeep Gladiator
overall
Summary
With 410 currently listed for sale near Chicago, IL and an average price of $31,450.00, 30.2% of 2021 Jeep Gladiators for sale on CarGurus are rated as good or great deals.
Favorably reviewed: Owners rated the 2021 Jeep Gladiator 5 / 5 stars.
96.6% of 2021 Gladiator models on CarGurus are accident free.
The 2021 Jeep Gladiator returns with a new turbo-diesel engine option, enhancing its off-road capabilities and overall performance while retaining its rugged design.
Why it stands out
The 2021 Jeep Gladiator distinguishes itself in the crowded midsize pickup market with its unique combination of rugged styling, impressive off-road capabilities, and a driving experience akin to the iconic Jeep Wrangler. This model introduces a new turbo-diesel engine option, which provides substantial torque and improved fuel efficiency—averaging 22.6 mpg during testing, significantly better than its gasoline counterpart. Owners appreciate its ability to tackle challenging terrains and the ease of customization with a plethora of aftermarket accessories available.
Moreover, the Gladiator's removable top and doors allow for an authentic open-air experience, making it a favorite for adventure enthusiasts. The cabin, while made for durability, offers comfort with features such as an upgraded Uconnect infotainment system, which enhances usability with Apple CarPlay and Android Auto compatibility. Despite some trade-offs in fuel economy and ride quality, the Gladiator remains compelling for buyers seeking both utility and an adventurous spirit, making it a versatile choice that stands out in the pickup segment.
Other model years to consider
- Average price: $28,021.00
- Good/great deal percentage: 29.5%
- User rating: 4.82 / 5
- Total listings: 281
- Average price: $35,366.00
- Good/great deal percentage: 30.0%
- User rating: 4.82 / 5
- Total listings: 270
- Average price: $35,410.00
- Good/great deal percentage: 32.3%
- User rating: 4.2 / 5
- Total listings: 381
This analysis is based on CarGurus' proprietary market data from May 5, 2026, CarGurus experts' opinions, and generative AI.
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5.0 Overall rating
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Anonymous
Reviewed a 2021 Jeep Gladiator on Jul 7, 2025
Just what I wanted, rugged but tech savvy. Been out of the Jeep world for a bit glad to get behind the wheel of one again!
John G
Reviewed a 2021 Jeep Mojave Crew Cab 4WD on Dec 2, 2024
The vehicle and outfitting is excellent. I am extremely satisfied with the features. I think compared to other models, it has the best package for the price. I don’t believe it is missing anything I desired!
Dave M
Reviewed a 2021 Jeep Gladiator on Jun 17, 2021
I absolutely love my Jeep Gladiator. I call it a truck with a sense of adventure, and it’s American Made.
Eric H
Reviewed a 2021 Jeep Gladiator on Jul 6, 2021
I really like my 2021 Gladiator Mojave, because it is everything a Jeep should be, plus more! I find the ride to be smooth, the interior to be well laid out, comfortable, and roomy. I like the 5 bed on the Jeep/truck, and have used it several times already. Only issue I have with my Gladiator is its gas mileage. I have the 3.6 motor, and am only averaging 17.2 mpg city and highway driving combined.
2021 Jeep Gladiator Trims
| Trim type | MSRP |
|---|---|
| Freedom Crew Cab 4WD | $40,705 |
| Sport S Crew Cab 4WD | $38,045 |
| High Altitude Crew Cab 4WD | $52,210 |
| Willys Crew Cab 4WD | $40,305 |
| Overland Crew Cab 4WD | $41,105 |
| Sport Crew Cab 4WD | $34,645 |
| Mojave Crew Cab 4WD | $44,925 |
| Rubicon Crew Cab 4WD | $44,925 |
2021 Jeep Gladiator Price Trends
CarGurus tracks the prices of millions of used car listings every year. See how the average price of 2021 Jeep Gladiator prices has changed over time.
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