Used Jeep Pickup Trucks for Sale inChicago, IL
368 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- Year:
- 2026
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 285 hp 3.6L V6
- Exterior color:
- 41
- Fuel type:
- Gasoline
- Interior color:
- Brown (Heritage Tan/Black)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 79
- Stock #:
- D260948A
- VIN:
- 1C6PJTAG3TL175460
Sponsored by Hawk Chrysler Jeep Dodge RAM
2026 Jeep Gladiator
Willys '41 4dr Crew Cab 4WD
79 mi
Forest Park, IL
10 mi away
Great Deal
$43,375
- 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:
- Fathom Blue Pearlcoat
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 18,649
- Stock #:
- Q42310A
- VIN:
- 1C6PJTAG1SL509175
Sponsored Listing
2025 Jeep Gladiator
NightHawk Crew Cab 4WD
18,649 mi
Algonquin, IL
41 mi away
Good Deal
$36,866
- 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:
- 47,835
- Stock #:
- JU18396A
- VIN:
- 1C6JJTBG4LL154363
Sponsored Listing
2020 Jeep Gladiator
Rubicon Crew Cab 4WD
47,835 mi
Des Plaines, IL
18 mi away
Fair Deal
$33,873
- 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:
- Red (Burgundy)
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Manual
- Mileage:
- 38,673
- Stock #:
- 28432430
- VIN:
- 1C6HJTAG6ML611076
New arrival
2021 Jeep Gladiator
Sport Crew Cab 4WD
38,673 mi
Store transfer to Oak Lawn, IL
Price includes $699 shipping
Fair Deal
$28,697
- 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:
- Sting-Gray Clearcoat
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 44,035
- Stock #:
- F5013
- VIN:
- 1C6HJTAG9NL159058
2022 Jeep Gladiator
Willys Crew Cab 4WD
44,035 mi
Saint Charles, IL
35 mi away
Fair Deal
$29,847
- 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:
- 38,891
- Stock #:
- 3501C
- VIN:
- 1C6HJTFG2NL107375
Price drop
-$2,125
2022 Jeep Gladiator
Overland Crew Cab 4WD
38,891 mi
Elmhurst, IL
17 mi away
Great Deal
$29,263
$27,138
- 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:
- 57,085
- Stock #:
- C9907A
- VIN:
- 1C6HJTAG8LL120104
Price drop
-$591
2020 Jeep Gladiator
Sport Crew Cab 4WD
57,085 mi
St Charles, IL
34 mi away
Good Deal
$25,999
$25,408
- 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:
- 39,388
- Stock #:
- P4556
- VIN:
- 1C6JJTBGXLL120315
2020 Jeep Gladiator
Rubicon Crew Cab 4WD
39,388 mi
Countryside, IL
14 mi away
Fair Deal
$33,310
- 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:
- Anvil Clearcoat
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 4,912
- Stock #:
- PD2056
- VIN:
- 1C6PJTAG0SL541504
2025 Jeep Gladiator
Sport Crew Cab 4WD
4,912 mi
Chicago, IL
9 mi away
Good Deal
$34,410
- 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:
- Black Clearcoat
- Combined gas mileage:
- 25 MPG
- Fuel type:
- Diesel
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 47,501
- Stock #:
- P1497
- VIN:
- 1C6JJTAM3NL118271
2022 Jeep Gladiator
Sport Crew Cab 4WD
47,501 mi
Crystal Lake, IL
43 mi away
Great Deal
$28,901
- 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:
- Bright White Clearcoat
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 79,957
- Stock #:
- SB2626
- VIN:
- 1C6JJTEG2ML524349
2021 Jeep Gladiator
Mojave Crew Cab 4WD
79,957 mi
Libertyville, IL
32 mi away
Fair Deal
$30,403
- 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:
- Crystal Metallic
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 87,108
- Stock #:
- T261997A
- VIN:
- 1C6HJTFG6LL198583
Price drop
-$1,796
2020 Jeep Gladiator
Overland Crew Cab 4WD
87,108 mi
Kenosha, WI
50 mi away
Great Deal
$25,386
$23,979
- 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:
- 35,016
- Stock #:
- C7539
- VIN:
- 1C6JJTEG8PL577285
2023 Jeep Gladiator
Mojave Crew Cab 4WD
35,016 mi
Crystal Lake, IL
42 mi away
Fair Deal
$36,924
- 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:
- White
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 65,500
- Stock #:
- 31-26315AA
- VIN:
- 1C6JJTBG1ML595630
Price drop
-$1,087
2021 Jeep Gladiator
Rubicon Crew Cab 4WD
65,500 mi
Chesterton, IN
33 mi away
Great Deal
$28,880
$27,792
- 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:
- 37,943
- Stock #:
- SL0349A
- VIN:
- 1C6JJTEG3ML524389
2021 Jeep Gladiator
Mojave Crew Cab 4WD
37,943 mi
Joliet, IL
37 mi away
Good Deal
$33,800
- 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 (Granite Crystal Metallic Clearcoat)
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 27,374
- Stock #:
- P7442
- VIN:
- 1C6HJTAG2PL562138
2023 Jeep Gladiator
Willys Crew Cab 4WD
27,374 mi
Crystal Lake, IL
42 mi away
Good Deal
$32,179
- 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:
- Red Clearcoat
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 66,648
- Stock #:
- J1249A
- VIN:
- 1C6HJTAG3LL131513
2020 Jeep Gladiator
Sport Crew Cab 4WD
66,648 mi
Crystal Lake, IL
43 mi away
Good Deal
$24,816
- 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:
- 6-Speed Manual
- Mileage:
- 71,325
- Stock #:
- J4963A
- VIN:
- 1C6HJTFG5LL106640
2020 Jeep Gladiator
Overland Crew Cab 4WD
71,325 mi
Fox Lake, IL
46 mi away
Fair Deal
$28,402
- 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 Clearcoat
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Manual
- Mileage:
- 42,466
- Stock #:
- 48108A
- VIN:
- 1C6JJTAG8ML526578
Price drop
-$687
2021 Jeep Gladiator
Sport Crew Cab 4WD
42,466 mi
Antioch, IL
47 mi away
Good Deal
$27,735
$27,048
- 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:
- 83,111
- Stock #:
- H4688A
- VIN:
- 1C6HJTFG4NL145500
2022 Jeep Gladiator
Overland Crew Cab 4WD
83,111 mi
Highland, IN
25 mi away
Good Deal
$26,886
- 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:
- 17,144
- Stock #:
- JC546
- VIN:
- 1C6HJTAG3PL556896
2023 Jeep Gladiator
Sport S Crew Cab 4WD
17,144 mi
Naperville, IL
30 mi away
Good Deal
$31,890
- 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:
- High Velocity Clearcoat
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Dark Saddle/Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 91,676
- Stock #:
- T2662
- VIN:
- 1C6JJTEG6PL510152
2023 Jeep Gladiator
Mojave Crew Cab 4WD
91,676 mi
Burbank, IL
13 mi away
Good Deal
$28,735
- 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:
- 70,817
- Stock #:
- BP3808
- VIN:
- 1C6JJTBM0ML600760
Price drop
-$900
2021 Jeep Gladiator
Rubicon Crew Cab 4WD
70,817 mi
Arlington Heights, IL
26 mi away
Good Deal
$34,288
$33,388
- 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:
- White
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 14,000
- Stock #:
- DMF1357AA
- VIN:
- 1C6PJTAG5SL526318
Sponsored Listing
2025 Jeep Gladiator
Sport S Crew Cab 4WD
14,000 mi
Michigan City, IN
40 mi away
Fair Deal
