Used Jeep Gladiator for Sale nearChicago, IL
638 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- Year:
- 2021
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 285 hp 3.6L V6
- Exterior color:
- Sting-Gray Clearcoat
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 41,453
- Stock #:
- M26231A
- VIN:
- 1C6HJTAG2ML537137
Sponsored by Palmen Kia of Kenosha
2021 Jeep Gladiator
Willys Crew Cab 4WD
41,453 mi
$29,746
- Year:
- 2023
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 285 hp 3.6L V6
- Exterior color:
- Gray
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 81,884
- Stock #:
- B5N514444
- VIN:
- 1C6HJTFGXPL514444
Sponsored Listing
2023 Jeep Gladiator
Overland Crew Cab 4WD
81,884 mi
$24,902
- Year:
- 2022
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 285 hp 3.6L V6
- Exterior color:
- Bright White Clearcoat
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 59,473
- Stock #:
- A135191
- VIN:
- 1C6JJTEG7NL135191
Sponsored Listing
2022 Jeep Gladiator
Mojave Crew Cab 4WD
59,473 mi
$32,876
- Year:
- 2020
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 285 hp 3.6L V6
- Exterior color:
- White
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 53,426
- Stock #:
- 29121367T
- VIN:
- 1C6HJTFG0LL121367
2020 Jeep Gladiator
Overland Crew Cab 4WD
53,426 mi
$29,233
- Year:
- 2022
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 285 hp 3.6L V6
- Exterior color:
- Bright White Clearcoat
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 34,601
- Stock #:
- A5000
- VIN:
- 1C6HJTFG3NL114965
2022 Jeep Gladiator
Overland Crew Cab 4WD
34,601 mi
$33,071
- Year:
- 2025
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 285 hp 3.6L V6
- Exterior color:
- Bright White Clearcoat
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 9,578
- Stock #:
- C9711
- VIN:
- 1C6PJTAG9SL508114
2025 Jeep Gladiator
Sport S Crew Cab 4WD
9,578 mi
$34,408
- Year:
- 2023
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 285 hp 3.6L V6
- Exterior color:
- Sarge Green Clearcoat
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 87,088
- Stock #:
- P7120
- VIN:
- 1C6JJTEG7PL509026
-$1,946
2023 Jeep Gladiator
Mojave Crew Cab 4WD
87,088 mi
$32,045
$30,099
- Year:
- 2022
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 260 hp 3L V6 Diesel
- Exterior color:
- Gray (Granite Crystal Metallic Clearcoat)
- Combined gas mileage:
- 25 MPG
- Fuel type:
- Diesel
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 52,013
- Stock #:
- C9771A
- VIN:
- 1C6JJTBM1NL123967
2022 Jeep Gladiator
Rubicon Crew Cab 4WD
52,013 mi
$39,105
- Year:
- 2021
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 285 hp 3.6L V6
- Exterior color:
- Gray
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 45,173
- Stock #:
- 29003662
- VIN:
- 1C6JJTEG0ML543305
2021 Jeep Gladiator
Mojave Crew Cab 4WD
45,173 mi
$32,998
- Year:
- 2023
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 285 hp 3.6L V6
- Exterior color:
- Bright White Clearcoat
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 22,821
- Stock #:
- H26181A
- VIN:
- 1C6HJTAG9PL541075
2023 Jeep Gladiator
Sport S Crew Cab 4WD
22,821 mi
$30,603
- Year:
- 2023
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 285 hp 3.6L V6
- Exterior color:
- Bright White Clearcoat
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 90,808
- Stock #:
- 22606A
- VIN:
- 1C6HJTFG5PL506199
2023 Jeep Gladiator
Overland Crew Cab 4WD
90,808 mi
$28,028
- Year:
- 2020
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 285 hp 3.6L V6
- Exterior color:
- Hydro Blue Pearlcoat
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 42,759
- Stock #:
- GAM6542
- VIN:
- 1C6HJTFG2LL157304
2020 Jeep Gladiator
Overland Crew Cab 4WD
42,759 mi
$30,576
- Year:
- 2022
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 285 hp 3.6L V6
- Exterior color:
- Gray (Granite Crystal Metallic Clearcoat)
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Global Black/Steel Gray
- Transmission:
- 8-Speed Automatic
- Mileage:
- 33,496
- Stock #:
- PM21443A
- VIN:
- 1C6HJTAG9NL153034
2022 Jeep Gladiator
Sport Crew Cab 4WD
33,496 mi
$30,353
Recommended model year:
2021 Jeep Gladiator
Shop 2021 Jeep Gladiator »With 421 currently listed for sale near Chicago, IL and an average price of $31,444.00, 23.8% 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.
88.4% of 2021 Gladiator models on CarGurus are accident free.
The 2021 Jeep Gladiator features a new turbo-diesel engine option, providing 260 horsepower and 442 lb-ft of torque, enhancing its off-road capabilities and fuel efficiency.
- Year:
- 2020
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 285 hp 3.6L V6
- Exterior color:
- White
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 76,996
- Stock #:
- L157533
- VIN:
- 1C6HJTAG7LL157533
2020 Jeep Gladiator
Sport S Crew Cab 4WD
76,996 mi
$27,784
- Year:
- 2024
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 285 hp 3.6L V6
- Exterior color:
- Anvil Clear Coat
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 25,691
- Stock #:
- C26507A
- VIN:
- 1C6HJTAG9RL134179
2024 Jeep Gladiator
Willys Crew Cab 4WD
25,691 mi
$37,036
- Year:
- 2023
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 285 hp 3.6L V6
- Exterior color:
- Black Clearcoat
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 67,733
- Stock #:
- J6Y514691
- VIN:
- 1C6HJTFG5PL514691
2023 Jeep Gladiator
High Altitude Crew Cab 4WD
67,733 mi
$29,388
- Year:
- 2020
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 285 hp 3.6L V6
- Exterior color:
- Gator Clearcoat
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 77,931
- Stock #:
- LL165277A
- VIN:
- 1C6HJTAG0LL165277
-$500
2020 Jeep Gladiator
Sport Crew Cab 4WD
77,931 mi
$25,059
$24,559
- Year:
- 2020
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 285 hp 3.6L V6
- Exterior color:
- Black Clearcoat
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 88,706
- Stock #:
- P3930
- VIN:
- 1C6JJTBG7LL199054
2020 Jeep Gladiator
Rubicon Crew Cab 4WD
88,706 mi
$30,430
- Year:
- 2021
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 285 hp 3.6L V6
- Exterior color:
- Gray
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 66,836
- Stock #:
- L610086
- VIN:
- 1C6JJTBG4ML610086
2021 Jeep Gladiator
Rubicon Crew Cab 4WD
66,836 mi
$32,095
- Year:
- 2023
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 285 hp 3.6L V6
- Exterior color:
- Gray
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 81,884
- Stock #:
- B5N514444
- VIN:
- 1C6HJTFGXPL514444
2023 Jeep Gladiator
Overland Crew Cab 4WD
81,884 mi
$24,902
- Year:
- 2020
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 285 hp 3.6L V6
- Exterior color:
- Billet Silver Metallic Clearcoat
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 91,976
- Stock #:
- X0653C
- VIN:
- 1C6JJTBG0LL118430
2020 Jeep Gladiator
Rubicon Crew Cab 4WD
91,976 mi
$29,327
- Year:
- 2021
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 260 hp 3L V6 Diesel
- Exterior color:
- Bright White Clearcoat
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Diesel
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 70,811
- Stock #:
- BP3808
- VIN:
- 1C6JJTBM0ML600760
2021 Jeep Gladiator
Rubicon Crew Cab 4WD
70,811 mi
$36,853
- Year:
- 2021
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 285 hp 3.6L V6
- Exterior color:
- Gray (Granite Crystal Metallic Clearcoat)
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 86,675
- Stock #:
- 33-1401CG
- VIN:
- 1C6HJTAG8ML583233
Sponsored Listing
2021 Jeep Gladiator
Sport Crew Cab 4WD
86,675 mi
$25,272
FAQs
How much does the Jeep Gladiator cost in Chicago, IL?
Is the Jeep Gladiator a good car?
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Is the Jeep Gladiator safe?
What fuel types are available?
4.8 Overall rating
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.
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What people say
Jeff M
Reviewed a 2021 Jeep Gladiator on May 18, 2026
Everything I wanted and more than I expected, even my wife likes it and she didn’t like them until I took her for a ride in it
Mindy P
Reviewed a 2025 Jeep Mojave Crew Cab 4WD on Jul 19, 2025
Big fan of the Mojave X features. Love the ride and the capabilities.
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!
Dominic K
Reviewed a 2023 Jeep Gladiator on Apr 10, 2026
Doors off, roof off. Wana hit any trail? Go for it. Take it to the beach? Go for it. Snowing hard? Not a worry. Expensive? Yes. Good on gas? No. Look back at the jeep when you leave it? Yes every time. Loved this gladiator. Name speaks for itself.
Jeep Gladiator Trims
| Trim type | MSRP |
|---|---|
| Mojave X Crew Cab 4WD | $60,690 |
| Rubicon X Crew Cab 4WD | $59,995 |
| Sport Crew Cab 4WD | $39,300 |
| Sahara Crew Cab 4WD | $47,595 |
| Willys '41 4dr Crew Cab 4WD | $47,840 |
| Mojave Crew Cab 4WD | $52,695 |
| Rubicon Crew Cab 4WD | $52,000 |
| Sport S Crew Cab 4WD | $42,495 |
Jeep Gladiator Price Trends
CarGurus tracks the prices of millions of used car listings every year. See how the average price of Jeep Gladiator prices has changed over time.
See more price trendsCarGurus recommends the 2021 Jeep Gladiator
Summary
With 421 currently listed for sale near Chicago, IL and an average price of $31,444.00, 23.8% 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.
88.4% of 2021 Gladiator models on CarGurus are accident free.
The 2021 Jeep Gladiator features a new turbo-diesel engine option, providing 260 horsepower and 442 lb-ft of torque, enhancing its off-road capabilities and fuel efficiency.
Why it stands out
The 2021 Jeep Gladiator stands out in the midsize pickup truck segment due to its unique blend of ruggedness and versatility. Built on the Wrangler platform, it offers a distinctive design that appeals to adventure seekers. The Gladiator is equipped with a new turbo-diesel engine option, which not only boosts performance but also improves fuel economy compared to its gasoline counterpart. Its removable top and doors, along with a host of aftermarket accessories, allow for a personalized driving experience. The Gladiator excels in off-road conditions, making it a favorite among those who prioritize adventure and outdoor activities.
Other model years to consider
- Average price: $29,452.00
- Good/great deal percentage: 22.3%
- User rating: 4.83 / 5
- Total listings: 300
- Average price: $32,047.00
- Good/great deal percentage: 25.1%
- User rating: 4.2 / 5
- Total listings: 395
- Average price: $34,362.00
- Good/great deal percentage: 25.5%
- User rating: 4.82 / 5
- Total listings: 271
These recommendations are based on CarGurus' proprietary market data from July 14, 2026, CarGurus experts' opinions, and generative AI.
Recent expert test drives
2025 Jeep Gladiator
- Expert review5/10
- MSRP$38,100-$61,100
- Avg. price$44,720
- User rating5
2024 Jeep Gladiator
- Expert review7/10
- MSRP$37,895-$62,995
- Avg. price$39,225
- User rating4.5
2020 Jeep Gladiator
- Expert review8/10
- MSRP$33,545-$54,845
- Avg. price$28,438
- User rating4.8286
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