Used Jeep Pickups for Sale near Chicago, Illinois
Sort
Filters
941 results
Location
Body Type
Popular Body Types
Price
Mileage
Make, Model, and Trim
Make
Year
Chassis Options
Cab Type
Chassis Type
Drivetrain
Engine Manufacturer
Engine Cylinders
Color
State
Used 2024 Jeep Gladiator Sport Crew Cab
$30,706
speed 41,155 mi
sell
Key features
- Gasoline
- 3.6L Naturally Aspirated V6
- 4x4
location_on
Classic Chevrolet Fleet & Commercial Sales
Grapevine, TX (806.4 mi)
(817) 809-9758
Used 2026 Jeep Gladiator Mojave Crew Cab
$44,220
speed 15,339 mi
sell
Key features
- Gasoline
- 3.6 L
- 4x4
location_on
Klement Chrysler Jeep Dodge RAM
Decatur, TX (807.7 mi)
(940) 399-5408
Used 2025 Jeep Gladiator Mojave Crew Cab
$49,680
speed 14,648 mi
sell
Key features
- Gasoline
- Regular Unleaded V-6 3.6 L/220
- 4WD
location_on
James Wood Chevrolet of Decatur
Decatur, TX (807.7 mi)
(940) 398-0965
Used 2025 Jeep Gladiator Sport Crew Cab
$33,441
speed 51,404 mi
sell
Key features
- Gasoline
- Regular Unleaded V-6 3.6 L/220
- 4WD
location_on
Karl Klement Ford – Decatur
Decatur, TX (807.7 mi)
(940) 245-4642
Used 2020 Jeep Gladiator Rubicon Crew Cab
$32,500
speed 66,330 mi
sell
Key features
- Gasoline
- 4WD
- Rubicon
location_on
Grubbs Chrysler Dodge Jeep Ram of Wichita Falls
Wichita Falls, TX (809.7 mi)
(940) 532-9928
Used 2021 Jeep Gladiator Sport Crew Cab
$31,600
speed 29,763 mi
sell
Key features
- Gasoline
- 4WD
- Willys
location_on
Crosstown Chrysler Dodge Jeep Ram Fiat
Littleton, NH (810.6 mi)
(603) 614-5372
Used 2026 Jeep Gladiator Mojave Crew Cab
$45,600
speed 14,578 mi
sell
Key features
- Gasoline
- 4WD
- Mojave
location_on
Crosstown Chrysler Dodge Jeep Ram Fiat
Littleton, NH (810.6 mi)
(603) 614-5372
Used 2024 Jeep Gladiator Mojave Crew Cab
$43,480
speed 20,361 mi
sell
Key features
- Gasoline
- 4WD
- Mojave
location_on
Tallahassee Ford
Tallahassee, FL (813.3 mi)
(850) 279-9333
Used 2023 Jeep Gladiator Mojave Crew Cab
$40,000
speed 11,374 mi
sell
Key features
- Gasoline
- 4WD
- Mojave
location_on
Five Star Ford
North Richland Hills, TX (816.6 mi)
(817) 646-4552
Used 2025 Jeep Gladiator Mojave Crew Cab
$44,891
speed 5,730 mi
sell
Key features
- Gasoline
- 4WD
- Mojave
location_on
Grappone Ford
Bow, NH (822.1 mi)
(855) 906-0865
Used 2021 Jeep Gladiator Rubicon Crew Cab
$30,691
speed 78,625 mi
sell
Key features
- Gasoline
- 4WD
- Rubicon
location_on
Grappone Ford
Bow, NH (822.1 mi)
(855) 906-0865
Used 2024 Jeep Gladiator Sport Crew Cab
$39,995
speed 13,425 mi
sell
Key features
- Gasoline
- 4WD
- Sport S
location_on
Tasca Chrysler Dodge Jeep Ram FIAT - Johnston
Johnston, RI (827.4 mi)
(401) 336-6434
Used 2024 Jeep Gladiator Sport Crew Cab
$37,593
speed 39,893 mi
sell
Key features
- Gasoline
- 4WD
- Texas Trail
location_on
Waxahachie Dodge Chrysler Jeep Ram
Waxahachie, TX (829.3 mi)
(469) 449-9298
Used 2023 Jeep Gladiator Rubicon Crew Cab
$34,646
speed 77,370 mi
sell
Key features
- Gasoline
- 4WD
- Rubicon
location_on
Waxahachie Dodge Chrysler Jeep Ram
Waxahachie, TX (829.3 mi)
(469) 449-9298
Used 2024 Jeep Gladiator Sport Crew Cab
$30,490
speed 24,548 mi
sell
Key features
- Gasoline
- 4WD
- Sport S
location_on
Waxahachie Dodge Chrysler Jeep Ram
Waxahachie, TX (829.3 mi)
(469) 449-9298
Used 2026 Jeep Gladiator Mojave Crew Cab
$45,280
speed 11,926 mi
sell
Key features
- Gasoline
- 4WD
- Mojave
location_on
Waxahachie Dodge Chrysler Jeep Ram
Waxahachie, TX (829.3 mi)
(469) 449-9298
Used 2025 Jeep Gladiator Sport Crew Cab
$38,435
speed 22,311 mi
sell
Key features
- Gasoline
- 4WD
- Nighthawk
location_on
Waxahachie Dodge Chrysler Jeep Ram
Waxahachie, TX (829.3 mi)
(469) 449-9298
Used 2026 Jeep Gladiator Mojave Crew Cab
$45,055
speed 11,926 mi
sell
Key features
- Gasoline
- 4WD
- Mojave
location_on
Waxahachie Ford
Waxahachie, TX (831.7 mi)
(817) 842-2901
Used 2023 Jeep Gladiator Rubicon Crew Cab
$34,421
speed 77,370 mi
sell
Key features
- Gasoline
- 4WD
- Rubicon
location_on
Waxahachie Ford
Waxahachie, TX (831.7 mi)
(817) 842-2901
Used 2024 Jeep Gladiator Sport Crew Cab
$30,265
speed 24,548 mi
sell
Key features
- Gasoline
- 4WD
- Sport S
location_on
Waxahachie Ford
Waxahachie, TX (831.7 mi)
(817) 842-2901
Used 2025 Jeep Gladiator Sport Crew Cab
$38,210
speed 22,311 mi
sell
Key features
- Gasoline
- 4WD
- Nighthawk
location_on
Waxahachie Ford
Waxahachie, TX (831.7 mi)
(817) 842-2901
Used 2024 Jeep Gladiator Sport Crew Cab
$37,368
speed 39,893 mi
sell
Key features
- Gasoline
- 4WD
- Texas Trail
location_on
Waxahachie Ford
Waxahachie, TX (831.7 mi)
(817) 842-2901
Used 2022 Jeep Gladiator Sport Crew Cab
$31,588
speed 45,678 mi
sell
Key features
- Gasoline
- 4WD
- Sport
location_on
495 Chrysler Jeep Dodge Ram
Lowell, MA (835.1 mi)
(978) 213-1575
Used 2022 Jeep Gladiator Sport Crew Cab
$30,475 List Price
$28,132
speed 68,515 mi
sell
Key features
- Gasoline
- 3.6L V6 24V VVT
- 4WD
location_on
McGovern Chrysler Jeep Dodge Ram of Newton
Newton, MA (840.5 mi)
(617) 762-5732
Used 2022 Jeep Gladiator Mojave Crew Cab
$37,625 List Price
$35,201
speed 51,765 mi
sell
Key features
- Gasoline
- 3.6L V6 24V VVT
- 4WD
location_on
McGovern Chrysler Jeep Dodge Ram of Newton
Newton, MA (840.5 mi)
(617) 762-5732
Used 2021 Jeep Gladiator Mojave Crew Cab
$26,385
speed 102,848 mi
sell
Key features
- Gasoline
- 4WD
- Mojave
location_on
Empire Ford Inc.
Fall River, MA (847.3 mi)
(508) 374-9080
Used 2025 Jeep Gladiator Mojave Crew Cab
$46,885
speed 10,865 mi
sell
Key features
- Gasoline
- 4WD
- Mojave
location_on
Empire Ford Inc.
Fall River, MA (847.3 mi)
(508) 374-9080
Used 2022 Jeep Gladiator Mojave Crew Cab
$34,780
speed 64,444 mi
sell
Key features
- Gasoline
- 3.6L V6 Cylinder Engine
- 4WD
location_on
Central Chrysler Dodge Jeep Ram of Raynham
Raynham, MA (850.8 mi)
(508) 802-4929
Used 2022 Jeep Gladiator Overland Crew Cab
$32,985
speed 44,299 mi
sell
Key features
- Gasoline
- 3.6L V6 Cylinder Engine
- 4WD
location_on
Central Chrysler Dodge Jeep Ram of Raynham
Raynham, MA (850.8 mi)
(508) 802-4929
Used 2022 Jeep Gladiator Sport Crew Cab
$30,980
speed 37,063 mi
sell
Key features
- Gasoline
- 4x4
- Sport
location_on
McLaughlin Chevrolet, Inc.
Whitman, MA (855.5 mi)
(781) 713-1234
