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 2025 Jeep Gladiator Sport Crew Cab
$39,534
speed 9,559 mi
sell
Key features
- Gasoline
- V-6 cyl
- 4x4
location_on
McGovern Ford of Beverly
Beverly, MA (857.8 mi)
(978) 948-4545
Used 2024 Jeep Gladiator Rubicon Crew Cab
$48,100 List Price
$44,100
speed 18,245 mi
sell
Key features
- Gasoline
- 3.6L V6 Cylinder Engine
- 4WD
location_on
Jacksonville Chrysler Jeep Dodge RAM Westside
Jacksonville, FL (859.6 mi)
(904) 236-5982
Used 2021 Jeep Gladiator Mojave Crew Cab
$38,100 List Price
$37,100
speed 61,027 mi
sell
Key features
- Gasoline
- 3.6L V6 Cylinder Engine
- 4WD
location_on
Jacksonville Chrysler Jeep Dodge RAM Westside
Jacksonville, FL (859.6 mi)
(904) 236-5982
Used 2021 Jeep Gladiator Mojave Crew Cab
$31,100 List Price
$30,100
speed 88,642 mi
sell
Key features
- Gasoline
- 3.6L V6 Cylinder Engine
- 4WD
location_on
Jacksonville Chrysler Jeep Dodge RAM Westside
Jacksonville, FL (859.6 mi)
(904) 236-5982
Used 2020 Jeep Gladiator Sport Crew Cab
$22,507
speed 111,209 mi
sell
Key features
- Gasoline
- 4WD
- Sport
location_on
Duval Ford
Jacksonville, FL (865.3 mi)
(904) 364-1670
Used 2023 Jeep Gladiator Sport Crew Cab
$27,000
speed 83,653 mi
sell
Key features
- Gasoline
- 4WD
- Sport S
location_on
Duval Ford
Jacksonville, FL (865.3 mi)
(904) 364-1670
Used 2023 Jeep Gladiator Sport Crew Cab
$30,619
speed 41,949 mi
sell
Key features
- Gasoline
- 4WD
- Willys
location_on
DARCARS Orangepark Chrysler Jeep Dodge RAM
Jacksonville, FL (869.6 mi)
(904) 299-1867
Used 2023 Jeep Gladiator Overland Crew Cab
$28,000
speed 57,920 mi
sell
Key features
- Gasoline
- 4WD
- Overland
location_on
DARCARS Orangepark Chrysler Jeep Dodge RAM
Jacksonville, FL (869.6 mi)
(904) 299-1867
Used 2021 Jeep Gladiator Sport Crew Cab
$30,356
speed 29,438 mi
sell
Key features
- Gasoline
- 4WD
- Willys
location_on
DARCARS Orangepark Chrysler Jeep Dodge RAM
Jacksonville, FL (869.6 mi)
(904) 299-1867
Used 2020 Jeep Gladiator Overland Crew Cab
$28,522
speed 57,508 mi
sell
Key features
- Gasoline
- 4WD
- Overland
location_on
DARCARS Orangepark Chrysler Jeep Dodge RAM
Jacksonville, FL (869.6 mi)
(904) 299-1867
Used 2021 Jeep Gladiator Rubicon Crew Cab
$31,500
speed 62,224 mi
sell
Key features
- Gasoline
- 4WD
- Rubicon
location_on
DARCARS Orangepark Chrysler Jeep Dodge RAM
Jacksonville, FL (869.6 mi)
(904) 299-1867
Used 2021 Jeep Gladiator Mojave Crew Cab
$29,541
speed 91,308 mi
sell
Key features
- Gasoline
- 4WD
- Mojave
location_on
DARCARS Orangepark Chrysler Jeep Dodge RAM
Jacksonville, FL (869.6 mi)
(904) 299-1867
Used 2020 Jeep Gladiator Rubicon Crew Cab
$31,355
speed 68,492 mi
sell
Key features
- Gasoline
- 4WD
- Rubicon
location_on
DARCARS Orangepark Chrysler Jeep Dodge RAM
Jacksonville, FL (869.6 mi)
(904) 299-1867
Used 2020 Jeep Gladiator Overland Crew Cab
$27,183
speed 85,187 mi
sell
Key features
- Gasoline
- 4x4
- Overland
location_on
McGovern Chevrolet of Plymouth Truck Center
Plymouth, MA (872.1 mi)
(774) 460-8126
Used 2021 Jeep Gladiator Mojave Crew Cab
$35,183
speed 42,516 mi
sell
Key features
- Gasoline
- 4x4
- Mojave
location_on
McGovern Chevrolet of Plymouth Truck Center
Plymouth, MA (872.1 mi)
(774) 460-8126
Used 2020 Jeep Gladiator Sport Crew Cab
$24,364
speed 65,729 mi
sell
Key features
- Gasoline
- 4WD
- Sport
location_on
Arundel Ford
Arundel, ME (876.7 mi)
(207) 569-3620
Used 2023 Jeep Gladiator Sport Crew Cab
$36,425 List Price
$31,320
speed 52,025 mi
sell
Key features
- Gasoline
- Regular Unleaded V-6 3.6 L/220
- 4WD
location_on
Garber Ford
Green Cove Springs, FL (883.6 mi)
(877) 563-8843
Used 2023 Jeep Gladiator Sport Crew Cab
$37,901 List Price
$30,647
speed 37,518 mi
sell
Key features
- Gasoline
- Regular Unleaded V-6 3.6 L/220
- 4WD
location_on
Garber Ford
Green Cove Springs, FL (883.6 mi)
(877) 563-8843
Used 2024 Jeep Gladiator Sport Crew Cab
$42,914 List Price
$38,391
speed 12,168 mi
sell
Key features
- Gasoline
- Regular Unleaded V-6 3.6 L/220
- 4WD
location_on
Garber Ford
Green Cove Springs, FL (883.6 mi)
(877) 563-8843
Used 2021 Jeep Gladiator Sport Crew Cab
$29,686
speed 65,832 mi
sell
Key features
- Gasoline
- Regular Unleaded V-6 3.6 L/220
- 4WD
location_on
Garber Ford
Green Cove Springs, FL (883.6 mi)
(877) 563-8843
Used 2023 Jeep Gladiator Overland Crew Cab
$35,961
speed 31,764 mi
sell
Key features
- Gasoline
- Regular Unleaded V-6 3.6 L/220
- 4WD
location_on
Garber Ford
Green Cove Springs, FL (883.6 mi)
(877) 563-8843
Used 2023 Jeep Gladiator Mojave Crew Cab
$41,478 List Price
$38,176
speed 21,229 mi
sell
Key features
- Gasoline
- 4WD
- Mojave
location_on
Parks Ford of Gainesville
Gainesville, FL (888.5 mi)
(352) 225-7856
Used 2020 Jeep Gladiator Rubicon Crew Cab
$34,996 List Price
$34,605
speed 54,168 mi
sell
Key features
- Gasoline
- 4WD
- Rubicon
location_on
Parks Ford of Gainesville
Gainesville, FL (888.5 mi)
(352) 225-7856
Used 2021 Jeep Gladiator Sport Crew Cab
$27,399
speed 50,539 mi
sell
Key features
- Gasoline
- 4WD
- Sport
location_on
Doggett Ford of Beaumont
Beaumont, TX (890.8 mi)
(409) 498-5317
Used 2020 Jeep Gladiator Rubicon Crew Cab
$28,722
speed 87,878 mi
sell
Key features
- Gasoline
- 3.6L V6
- 4WD
location_on
Martin Chevrolet
Cleveland, TX (896.1 mi)
(346) 414-0962
Used 2020 Jeep Gladiator Mojave Crew Cab
$35,516
speed 34,800 mi
sell
Key features
- Gasoline
- Regular Unleaded V-6 3.6 L/220
- 4WD
location_on
Ken Garff Ford Cheyenne
Cheyenne, WY (896.2 mi)
(307) 788-2144
Used 2023 Jeep Gladiator Sport Crew Cab
$37,256
speed 19,571 mi
sell
Key features
- Diesel
- Intercooled Turbo Diesel V-6 3.0 L/182
- 4WD
location_on
Ken Garff Ford Cheyenne
Cheyenne, WY (896.2 mi)
(307) 788-2144
Used 2023 Jeep Gladiator Rubicon Crew Cab
$37,995
speed 56,530 mi
sell
Key features
- Diesel
- 3.0 Liter Turbo
- 4x4
location_on
Texas Dodge Chrysler Jeep RAM
Amarillo, TX (897.1 mi)
(806) 607-8892
Used 2020 Jeep Gladiator Sport Crew Cab
$22,625 List Price
$16,500
speed 129,898 mi
sell
Key features
- Gasoline
- 4WD
- Sport
location_on
Bozard Ford-Lincoln
St Augustine, FL (897.2 mi)
(904) 543-3823
Used 2020 Jeep Gladiator Mojave Crew Cab
$34,075 List Price
$29,500
speed 80,832 mi
sell
Key features
- Gasoline
- 4WD
- Mojave
location_on
Bozard Ford-Lincoln
St Augustine, FL (897.2 mi)
(904) 543-3823
