Jeep Gladiator Pickups for Sale near Chicago, Illinois
Sort
Filters
970 results
Location
Body Type
Popular Body Types
Price
Mileage
Make, Model, and Trim
Year
Chassis Options
Add-Ons
State
Used 2023 Jeep Gladiator Sport Crew Cab
$37,689 List Price
$34,999
speed 18,831 mi
sell
Key features
- Gasoline
- 4WD
- Sport
location_on
Mitchell Selig Ford
Windsor, CT (767.9 mi)
(860) 406-7275
Used 2022 Jeep Gladiator Rubicon Crew Cab
$38,899 List Price
$34,999
speed 59,761 mi
sell
Key features
- Gasoline
- 4WD
- Rubicon
location_on
Mitchell Selig Ford
Windsor, CT (767.9 mi)
(860) 406-7275
Used 2026 Jeep Gladiator Rubicon Crew Cab
$45,678 List Price
$41,999
speed 17,350 mi
sell
Key features
- Gasoline
- 4WD
- Rubicon
location_on
Mitchell Selig Ford
Windsor, CT (767.9 mi)
(860) 406-7275
Used 2020 Jeep Gladiator Rubicon Crew Cab
$29,587
speed 69,563 mi
sell
Key features
- Gasoline
- 4WD
- Rubicon
location_on
Hutson Motor Company
Moultrie, GA (775.7 mi)
(229) 785-4474
Used 2025 Jeep Gladiator Rubicon Crew Cab
$41,020
speed 18,382 mi
sell
Key features
- Gasoline
- 4WD
- Rubicon
location_on
Brandon Tomes CDJR
McKinney, TX (779.8 mi)
(940) 290-7471
Used 2023 Jeep Gladiator Mojave Crew Cab
$37,224
speed 20,325 mi
sell
Key features
- Gasoline
- 4WD
- Mojave
location_on
Brandon Tomes CDJR
McKinney, TX (779.8 mi)
(940) 290-7471
Used 2025 Jeep Gladiator Sport Crew Cab
$36,820
speed 7,475 mi
sell
Key features
- Gasoline
- 4WD
- Texas Trail
location_on
Brandon Tomes CDJR
McKinney, TX (779.8 mi)
(940) 290-7471
Used 2021 Jeep Gladiator Overland Crew Cab
$32,220
speed 37,787 mi
sell
Key features
- Gasoline
- 4WD
- Overland
location_on
Brandon Tomes CDJR
McKinney, TX (779.8 mi)
(940) 290-7471
Used 2020 Jeep Gladiator Mojave Crew Cab
$31,410
speed 50,645 mi
sell
Key features
- Gasoline
- 4WD
- Mojave 4x4
location_on
Hall Buick GMC
Tyler, TX (783.9 mi)
(903) 414-6762
Used 2022 Jeep Gladiator Sport Crew Cab
$26,437
speed 71,906 mi
sell
Key features
- Gasoline
- 3.6L V-6 DOHC, variable valve control, regular gasoline, engine with 285HP
- 4x4
location_on
Group 1 Chrysler Dodge Jeep Ram Rockwall
Rockwall, TX (784.2 mi)
(903) 751-3519
Used 2023 Jeep Gladiator Sport Crew Cab
$27,667
speed 49,584 mi
sell
Key features
- Gasoline
- Pentastar 3.6L V-6 DOHC, variable valve control, regular gasoline, engine with 285HP
- 4x4
location_on
Group 1 Chrysler Dodge Jeep Ram Rockwall
Rockwall, TX (784.2 mi)
(903) 751-3519
Used 2020 Jeep Gladiator Overland Crew Cab
$25,713
speed 81,349 mi
sell
Key features
- Gasoline
- 4WD
- Overland
location_on
Platinum Ford
Terrell, TX (789.6 mi)
(903) 226-8457
Used 2021 Jeep Gladiator Mojave Crew Cab
$33,114
speed 37,942 mi
sell
Key features
- Gasoline
- 4WD
- Mojave
location_on
Platinum Chrysler Dodge Ram Jeep
Terrell, TX (789.6 mi)
(214) 432-7133
Used 2026 Jeep Gladiator Sport Crew Cab
$38,149
speed 214 mi
sell
Key features
- Gasoline
- 4WD
- Sport
location_on
Hill-Kelly Dodge Chrysler Jeep RAM
Pensacola, FL (789.8 mi)
(850) 344-1701
Used 2021 Jeep Gladiator Rubicon Crew Cab
$36,279
speed 37,318 mi
sell
Key features
- Gasoline
- 4WD
- Rubicon
location_on
Hill-Kelly Dodge Chrysler Jeep RAM
Pensacola, FL (789.8 mi)
(850) 344-1701
Used 2020 Jeep Gladiator Mojave Crew Cab
$29,859
speed 101,657 mi
sell
Key features
- Gasoline
- 4WD
- Mojave
location_on
Hill-Kelly Dodge Chrysler Jeep RAM
Pensacola, FL (789.8 mi)
(850) 344-1701
Used 2023 Jeep Gladiator Sport Crew Cab
$34,264
speed 33,591 mi
sell
Key features
- Gasoline
- 4WD
- Sport S
location_on
Hill-Kelly Dodge Chrysler Jeep RAM
Pensacola, FL (789.8 mi)
(850) 344-1701
Used 2022 Jeep Gladiator Sport Crew Cab
$33,400 List Price
$29,500
speed 27,695 mi
sell
Key features
- Gasoline
- V6 Cylinder Engine
- 4x4
location_on
J. Allen Ford
Gulfport, MS (793.4 mi)
(228) 400-8076
Used 2020 Jeep Gladiator Overland Crew Cab
$33,175 List Price
$27,699
speed 64,412 mi
sell
Key features
- Gasoline
- V6 Cylinder Engine
- 4x4
location_on
J. Allen Ford
Gulfport, MS (793.4 mi)
(228) 400-8076
Used 2024 Jeep Gladiator Sport Crew Cab
$35,777
speed 18,318 mi
sell
Key features
- Gasoline
- Pentastar 3.6L V-6 DOHC, variable valve control, regular unleaded, engine with 285HP
- 4x4
location_on
Pete Moore Chevrolet
Pensacola, FL (794.2 mi)
(850) 805-8546
Used 2020 Jeep Gladiator Mojave Crew Cab
$30,076
speed 82,186 mi
sell
Key features
- Gasoline
- 4WD
- Mojave
location_on
Bill Utter Ford
Denton, TX (795.1 mi)
(940) 236-3247
New 2026 Jeep Gladiator Sport Crew Cab
$52,225 MSRP
$44,399
sell
Key features
- Gasoline
- 3.6 L
- 4WD
location_on
Huffines Chrysler Jeep Dodge Ram Lewisville
Lewisville, TX (799.1 mi)
(972) 947-2285
New 2026 Jeep Gladiator Sport Crew Cab
$53,145 MSRP
$43,900
sell
Key features
- Gasoline
- 3.6 L
- 4WD
location_on
Huffines Chrysler Jeep Dodge Ram Lewisville
Lewisville, TX (799.1 mi)
(972) 947-2285
New 2026 Jeep Gladiator Sport Crew Cab
$53,145 MSRP
$46,253
sell
Key features
- Gasoline
- 3.6 L
- 4WD
location_on
Huffines Chrysler Jeep Dodge Ram Lewisville
Lewisville, TX (799.1 mi)
(972) 947-2285
New 2026 Jeep Gladiator Rubicon Crew Cab
$66,265 MSRP
$53,900
sell
Key features
- Gasoline
- 3.6 L
- 4WD
location_on
Huffines Chrysler Jeep Dodge Ram Lewisville
Lewisville, TX (799.1 mi)
(972) 947-2285
New 2026 Jeep Gladiator Mojave Crew Cab
$65,895 MSRP
$52,900
sell
Key features
- Gasoline
- 3.6 L
- 4WD
location_on
Huffines Chrysler Jeep Dodge Ram Lewisville
Lewisville, TX (799.1 mi)
(972) 947-2285
New 2026 Jeep Gladiator Sport Crew Cab
$53,145 MSRP
$46,253
sell
Key features
- Gasoline
- 3.6 L
- 4WD
location_on
Huffines Chrysler Jeep Dodge Ram Lewisville
Lewisville, TX (799.1 mi)
(972) 947-2285
New 2026 Jeep Gladiator Sport Crew Cab
$53,145 MSRP
$44,900
sell
Key features
- Gasoline
- 3.6 L
- 4WD
location_on
Huffines Chrysler Jeep Dodge Ram Lewisville
Lewisville, TX (799.1 mi)
(972) 947-2285
New 2026 Jeep Gladiator Sport Crew Cab
$52,225 MSRP
$44,399
sell
Key features
- Gasoline
- 3.6 L
- 4WD
location_on
Huffines Chrysler Jeep Dodge Ram Lewisville
Lewisville, TX (799.1 mi)
(972) 947-2285
New 2026 Jeep Gladiator Sport Crew Cab
$52,550 MSRP
$45,729
sell
Key features
- Gasoline
- 3.6 L
- 4WD
location_on
Huffines Chrysler Jeep Dodge Ram Lewisville
Lewisville, TX (799.1 mi)
(972) 947-2285
