Used Jeep Pickup Trucks for Sale in Chicago, IL

358 results

2021 Jeep Gladiator

Mojave Crew Cab 4WD

64,318 miles

$33,772

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:: Sarge Green Clearcoat
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: Automatic
Mileage:: 64,318
Stock #:: PH1874
VIN:: 1C6JJTEGXML621590

2020 Jeep Gladiator

Rubicon Crew Cab 4WD

91,023 miles

$28,457

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:: Bright White Clearcoat
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: Automatic
Mileage:: 91,023
Stock #:: 15498
VIN:: 1C6JJTBG8LL110480

2020 Jeep Gladiator

Rubicon Crew Cab 4WD

83,218 miles

$30,337

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:: Bright White Clearcoat
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 83,218
Stock #:: T7729A
VIN:: 1C6JJTBG6LL118187

2023 Jeep Gladiator

Overland Crew Cab 4WD

61,075 miles

$25,891

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 Clear Coat
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 61,075
Stock #:: MCE2066
VIN:: 1C6HJTFG4PL552820

2025 Jeep Gladiator

Sport S Crew Cab 4WD

9,578 miles

$34,408

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

2020 Jeep Gladiator

Sport Altitude Crew Cab 4WD

74,495 miles

$25,194

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:: Bright White Clearcoat
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 74,495
Stock #:: B11240
VIN:: 1C6HJTAG1LL213501

2021 Jeep Gladiator

Sport Crew Cab 4WD

57,387 miles

$26,408

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:: 6-Speed Manual
Mileage:: 57,387
Stock #:: VP4122B
VIN:: 1C6HJTAG7ML558596

2021 Jeep Gladiator

Willys Crew Cab 4WD

69,545 miles

$26,861

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:: Billet Silver Metallic Clearcoat
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 69,545
Stock #:: R27340A
VIN:: 1C6HJTAG7ML543399

2023 Jeep Gladiator

Mojave Crew Cab 4WD

67,259 miles

$33,268

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:: Sting-Gray Clearcoat
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 67,259
Stock #:: LD60127A
VIN:: 1C6JJTEG2PL524758

2021 Jeep Gladiator

Mojave Crew Cab 4WD

64,318 miles

$33,772

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:: Sarge Green Clearcoat
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: Automatic
Mileage:: 64,318
Stock #:: PH1874
VIN:: 1C6JJTEGXML621590

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2023 Jeep Gladiator

Rubicon Crew Cab 4WD

36,830 miles

$36,001

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:: Silver Zynith Clearcoat
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 36,830
Stock #:: 23753
VIN:: 1C6JJTBGXPL570813

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2022 Jeep Gladiator

High Altitude Crew Cab 4WD

10,911 miles

$34,405

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:: 10,911
Stock #:: P1294
VIN:: 1C6HJTFG6NL128679

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2021 Jeep Gladiator

Willys Crew Cab 4WD

40,499 miles

$28,995

Good Deal

$563/mo est.

Third-party certified

Frankfort, IL

28 mi away

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:: Snazzberry Pearlcoat
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 40,499
Stock #:: 48788
VIN:: 1C6HJTAG7ML616920

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2023 Jeep Gladiator

Rubicon Crew Cab 4WD

20,598 miles

$38,377

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:: 20,598
Stock #:: 25243A
VIN:: 1C6JJTBG6PL530258

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2021 Jeep Gladiator

Overland Crew Cab 4WD

68,889 miles

$27,998

Good Deal

$543/mo est.

Third-party certified

Aurora, IL

36 mi away

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:: Black Clearcoat
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: Automatic
Mileage:: 68,889
Stock #:: NT26432A
VIN:: 1C6HJTFG3ML504110

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2023 Jeep Gladiator

Willys Crew Cab 4WD

45,934 miles

$29,990

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:: Automatic
Mileage:: 45,934
Stock #:: 260105A
VIN:: 1C6HJTAG7PL545187

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2023 Jeep Gladiator

Rubicon Crew Cab 4WD

8,114 miles

$39,215

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:: 8,114
Stock #:: C9704
VIN:: 1C6JJTBG1PL577083

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2020 Jeep Gladiator

Sport S Crew Cab 4WD

111,204 miles

$21,849

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:: Green
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 111,204
Stock #:: 160747
VIN:: 1C6HJTAG8LL160747

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2022 Jeep Gladiator

Rubicon Crew Cab 4WD

25,134 miles

$36,402

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:: Black Clearcoat
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 25,134
Stock #:: Q5508B
VIN:: 1C6JJTBG1NL104104

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2020 Jeep Gladiator

Sport Crew Cab 4WD

58,261 miles

$24,899

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:: 8-Speed Automatic
Mileage:: 58,261
Stock #:: K1241
VIN:: 1C6JJTAG0LL123709

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2020 Jeep Gladiator

Sport Crew Cab 4WD

77,931 miles

$25,247

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

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2021 Jeep Gladiator

Rubicon Crew Cab 4WD

120,838 miles

$25,873

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:: 8-Speed Automatic
Mileage:: 120,838
Stock #:: 12074
VIN:: 1C6JJTBG1ML567231

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2020 Jeep Gladiator

Rubicon Crew Cab 4WD

83,218 miles

$30,337

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:: Bright White Clearcoat
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 83,218
Stock #:: T7729A
VIN:: 1C6JJTBG6LL118187

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2023 Jeep Gladiator

Sport Crew Cab 4WD

29,865 miles

$29,390

Great Deal

$559/mo est.

Elk Grove Village, IL

21 mi away

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:: 29,865
Stock #:: NC3697
VIN:: 1C6HJTAG9PL552450

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Used Jeep Pickup Trucks for Sale in Chicago, IL

2021 Jeep Gladiator

$33,772

2020 Jeep Gladiator

$28,457

2020 Jeep Gladiator

$30,337

2023 Jeep Gladiator

$25,891

2025 Jeep Gladiator

$34,408

2020 Jeep Gladiator

$25,194

2021 Jeep Gladiator

$26,408

2021 Jeep Gladiator

$26,861

2023 Jeep Gladiator

$33,268

2021 Jeep Gladiator

$33,772

2023 Jeep Gladiator

$36,001

2022 Jeep Gladiator

$34,405

2021 Jeep Gladiator

$28,995

2023 Jeep Gladiator

$38,377

2021 Jeep Gladiator

$27,998

2023 Jeep Gladiator

$29,990

2023 Jeep Gladiator

$39,215

2020 Jeep Gladiator

$21,849

2022 Jeep Gladiator

$36,402

2020 Jeep Gladiator

$24,899

2020 Jeep Gladiator

$25,247

2021 Jeep Gladiator

$25,873

2020 Jeep Gladiator

$30,337

2023 Jeep Gladiator

$29,390

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