Best Pickup Trucks For Sale in Chicago, IL

1,750 results

2022 RAM 1500

Laramie Crew Cab 4WD

57,115 miles

$37,000

Year:: 2022
Make:: RAM
Model:: 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 395 hp 5.7L V8
Exterior color:: Delmonico Red Pearlcoat
Combined gas mileage:: 18 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 57,115
Stock #:: PRS1341
VIN:: 1C6SRFJT9NN435790

2023 Chevrolet Silverado 1500

RST Crew Cab 4WD

41,623 miles

$41,995

Year:: 2023
Make:: Chevrolet
Model:: Silverado 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 355 hp 5.3L V8
Exterior color:: Summit White
Combined gas mileage:: 18 MPG
Fuel type:: Gasoline
Interior color:: Jet Black
Transmission:: Automatic
Mileage:: 41,623
Stock #:: F4928
VIN:: 1GCUDEED8PZ258934

2022 Ford F-150

XLT SuperCrew 4WD

25,639 miles

$36,212

Year:: 2022
Make:: Ford
Model:: F-150
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 400 hp 3.5L V6
Exterior color:: Red
Combined gas mileage:: 20 MPG
Fuel type:: Gasoline
Interior color:: Black (Ebony)
Transmission:: Automatic
Mileage:: 25,639
Stock #:: P7092
VIN:: 1FTFW1E81NKE05714

2023 GMC Canyon

Denali Crew Cab 4WD

26,444 miles

$40,895

Good Deal

$779/mo est.

Third-party certified

Frankfort, IL

28 mi away

Year:: 2023
Make:: GMC
Model:: Canyon
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 310 hp 2.7L I4
Exterior color:: Summit White
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Jet Black/Teak
Transmission:: 8-Speed Automatic
Mileage:: 26,444
Stock #:: 48768
VIN:: 1GTP6FEK9P1170680

2022 RAM 1500

Laramie Crew Cab 4WD

21,223 miles

$41,000

Year:: 2022
Make:: RAM
Model:: 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 395 hp 5.7L V8
Exterior color:: Diamond Black
Combined gas mileage:: 18 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 21,223
Stock #:: N14853
VIN:: 1C6SRFJT3NN237979

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

56,815 miles

$36,123

Fair Deal

$700/mo est.

Third-party certified

Valparaiso, IN

40 mi away

Year:: 2022
Make:: Chevrolet
Model:: Silverado 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 355 hp 5.3L V8
Exterior color:: Black
Combined gas mileage:: 17 MPG
Fuel type:: Gasoline
Interior color:: Jet Black
Transmission:: Automatic
Mileage:: 56,815
Stock #:: U10320
VIN:: 3GCPYCEL4NG212592

2022 RAM 1500

Laramie Crew Cab 4WD

35,439 miles

$39,588

Year:: 2022
Make:: RAM
Model:: 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 395 hp 5.7L V8
Exterior color:: Gray (Granite Crystal Metallic Clearcoat)
Combined gas mileage:: 18 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 35,439
Stock #:: P04604
VIN:: 1C6SRFJT4NN449435

2023 Chevrolet Silverado 1500

RST Crew Cab 4WD

18,309 miles

$43,992

Year:: 2023
Make:: Chevrolet
Model:: Silverado 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 355 hp 5.3L V8
Exterior color:: Sterling Gray Metallic
Combined gas mileage:: 18 MPG
Fuel type:: Gasoline
Interior color:: Jet Black
Transmission:: Automatic
Mileage:: 18,309
Stock #:: PG7224
VIN:: 1GCUDEED5PZ329619

2022 RAM 1500

Laramie Crew Cab 4WD

36,620 miles

$40,495

Year:: 2022
Make:: RAM
Model:: 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 395 hp 5.7L V8
Exterior color:: Gray (Granite Crystal Metallic Clearcoat)
Combined gas mileage:: 18 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 36,620
Stock #:: F4901A
VIN:: 1C6SRFJT4NN466445

2021 Chevrolet Silverado 1500

RST Crew Cab 4WD

90,706 miles

$28,900

Year:: 2021
Make:: Chevrolet
Model:: Silverado 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 355 hp 5.3L V8
Exterior color:: Black
Combined gas mileage:: 17 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 90,706
Stock #:: CP7260
VIN:: 1GCUYEED2MZ281870

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2021 GMC Sierra 1500

SLT Crew Cab 4WD

89,760 miles

$33,395

Year:: 2021
Make:: GMC
Model:: Sierra 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 355 hp 5.3L V8
Exterior color:: Onyx Black
Fuel type:: Gasoline
Interior color:: Black
Transmission:: Automatic
Mileage:: 89,760
Stock #:: F4906
VIN:: 3GTU9DED9MG143394

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2022 RAM 1500

Big Horn Quad Cab 4WD

32,614 miles

$33,544

Year:: 2022
Make:: RAM
Model:: 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 305 hp 3.6L V6
Exterior color:: Bright White Clearcoat
Combined gas mileage:: 21 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 32,614
Stock #:: D14088
VIN:: 1C6RRFBG3NN418659

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2022 RAM 1500

Laramie Crew Cab 4WD

75,712 miles

$35,429

Year:: 2022
Make:: RAM
Model:: 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 395 hp 5.7L V8
Exterior color:: Diamond Black Crystal Pearlcoat
Combined gas mileage:: 18 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 75,712
Stock #:: D14029
VIN:: 1C6SRFJT2NN407488

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2023 Ford F-150

XL Regular Cab 4WD

12,360 miles

$29,995

Year:: 2023
Make:: Ford
Model:: F-150
Body type:: Pickup Truck
Doors:: 2 doors
Drivetrain:: Four-Wheel Drive
Engine:: 3.3L V6 Flex Fuel Vehicle
Exterior color:: Oxford White
Combined gas mileage:: 20 MPG
Fuel type:: Flex Fuel Vehicle
Interior color:: Black W/Medium Dark Slate
Transmission:: Automatic
Mileage:: 12,360
Stock #:: P23904
VIN:: 1FTMF1EBXPKG04685

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2022 Chevrolet Silverado 1500

Custom Crew Cab 4WD

34,045 miles

$29,900

Year:: 2022
Make:: Chevrolet
Model:: Silverado 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 310 hp 2.7L I4
Exterior color:: Black
Combined gas mileage:: 18 MPG
Fuel type:: Gasoline
Interior color:: Jet Black
Transmission:: 8-Speed Automatic
Mileage:: 34,045
Stock #:: CP7261
VIN:: 1GCPDBEK9NZ546419

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2023 RAM 1500

Big Horn Crew Cab 4WD

67,889 miles

$30,294

Year:: 2023
Make:: RAM
Model:: 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 260 hp 3L V6 Biodiesel
Exterior color:: Bright White Clearcoat
Combined gas mileage:: 25 MPG
Fuel type:: Biodiesel
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 67,889
Stock #:: P2966
VIN:: 1C6SRFFM1PN539601

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2022 RAM 1500

Big Horn Crew Cab 4WD

59,918 miles

$31,490

Year:: 2022
Make:: RAM
Model:: 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 305 hp 3.6L V6
Exterior color:: Diamond Black Crystal Pearlcoat
Combined gas mileage:: 21 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: Automatic
Mileage:: 59,918
Stock #:: 250626A
VIN:: 1C6RRFFG5NN232776

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2021 Jeep Gladiator

Overland Crew Cab 4WD

68,889 miles

$27,695

Good Deal

$537/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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2022 Chevrolet Silverado 1500

RST Crew Cab 4WD

66,934 miles

$35,661

Good Deal

$691/mo est.

Manufacturer certified

Niles, IL

16 mi away

Year:: 2022
Make:: Chevrolet
Model:: Silverado 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 355 hp 5.3L V8
Exterior color:: Black
Combined gas mileage:: 17 MPG
Fuel type:: Gasoline
Transmission:: Automatic
Mileage:: 66,934
Stock #:: GM6573A
VIN:: 3GCUYEED0NG105319

2022 RAM 1500

Laramie Crew Cab 4WD

26,344 miles

$39,995

Year:: 2022
Make:: RAM
Model:: 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 395 hp 5.7L V8
Exterior color:: Diamond Black Cry
Combined gas mileage:: 18 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: Automatic
Mileage:: 26,344
Stock #:: TB12X71A
VIN:: 1C6SRFJT5NN429887

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2022 Jeep Gladiator

High Altitude Crew Cab 4WD

10,911 miles

$34,491

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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2022 RAM 1500

Classic Warlock Crew Cab 4WD

116,467 miles

$23,400

Year:: 2022
Make:: RAM
Model:: 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 305 hp 3.6L V6
Exterior color:: Diamond Black Crystal Pearlcoat
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 116,467
Stock #:: WU212895
VIN:: 1C6RR7LG9NS176224

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2021 Jeep Gladiator

Rubicon Crew Cab 4WD

18,330 miles

$41,995

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:: Black Clearcoat
Combined gas mileage:: 24 MPG
Fuel type:: Diesel
Interior color:: Black
Transmission:: Automatic
Mileage:: 18,330
Stock #:: AS19366
VIN:: 1C6JJTBM1ML522702

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2022 GMC Sierra 1500

AT4 Crew Cab 4WD

13,566 miles

$48,000

Year:: 2022
Make:: GMC
Model:: Sierra 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 277 hp 3L I6 Diesel
Exterior color:: Titanium Rush Metallic
Combined gas mileage:: 24 MPG
Fuel type:: Diesel
Interior color:: Jet Black w/Kalahari Accents
Transmission:: Automatic
Mileage:: 13,566
Stock #:: E8111
VIN:: 1GTUUEET1NZ634264

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Best Pickup Trucks For Sale in Chicago, IL

2022 RAM 1500

$37,000

2023 Chevrolet Silverado 1500

$41,995

2022 Ford F-150

$36,212

2023 GMC Canyon

$40,895

2022 RAM 1500

$41,000

2022 Chevrolet Silverado 1500

$36,123

2022 RAM 1500

$39,588

2023 Chevrolet Silverado 1500

$43,992

2022 RAM 1500

$40,495

2021 Chevrolet Silverado 1500

$28,900

2021 GMC Sierra 1500

$33,395

2022 RAM 1500

$33,544

2022 RAM 1500

$35,429

2023 Ford F-150

$29,995

2022 Chevrolet Silverado 1500

$29,900

2023 RAM 1500

$30,294

2022 RAM 1500

$31,490

2021 Jeep Gladiator

$27,695

2022 Chevrolet Silverado 1500

$35,661

2022 RAM 1500

$39,995

2022 Jeep Gladiator

$34,491

2022 RAM 1500

$23,400

2021 Jeep Gladiator

$41,995

2022 GMC Sierra 1500

$48,000

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