Best Pickup Trucks For Sale inChicago, IL
1,795 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- Year:
- 2023
- Make:
- RAM
- Model:
- 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 305 hp 3.6L V6
- Exterior color:
- Flame Red Clearcoat
- Combined gas mileage:
- 21 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 27,284
- Stock #:
- M2207
- VIN:
- 1C6RRFFG6PN618433
Sponsored by Old Orchard Nissan
2023 RAM 1500
Big Horn Crew Cab 4WD
27,284 mi
Skokie, IL
14 mi away
Good Deal
$33,853
- Year:
- 2022
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 277 hp 3L I6 Diesel
- Exterior color:
- Dark Ash Metallic
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Diesel
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 69,806
- Stock #:
- P4386
- VIN:
- 3GCUDFETXNG689351
Sponsored Listing
2022 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
69,806 mi
Elgin, IL
39 mi away
Fair Deal
$39,407
- Year:
- 2023
- Make:
- Ford
- Model:
- F-150
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 400 hp 3.5L V6
- Exterior color:
- White
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 12,959
- Stock #:
- XXP1371
- VIN:
- 1FTFW1E87PKF51473
Sponsored Listing
2023 Ford F-150
XLT SuperCrew 4WD
12,959 mi
Michigan City, IN
40 mi away
Good Deal
$40,262
- 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
2021 Jeep Gladiator
Rubicon Crew Cab 4WD
65,500 mi
Chesterton, IN
33 mi away
Good Deal
$30,200
- 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
$30,347
- Year:
- 2023
- Make:
- RAM
- Model:
- 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 395 hp 5.7L V8
- Exterior color:
- Patriot Blue Pearlcoat
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 67,904
- Stock #:
- V260345A
- VIN:
- 1C6SRFFT2PN567849
2023 RAM 1500
Big Horn Crew Cab 4WD
67,904 mi
Orland Park, IL
22 mi away
Good Deal
$30,953
- 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:
- Pearl
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 64,410
- Stock #:
- M8201
- VIN:
- 1GCUYGED7NZ129211
2022 Chevrolet Silverado 1500
LTZ Crew Cab 4WD
64,410 mi
Crystal Lake, IL
42 mi away
Fair Deal
$37,908
- Year:
- 2022
- Make:
- Ford
- Model:
- Maverick
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 250 hp 2L I4
- Exterior color:
- White
- Fuel type:
- Gasoline
- Mileage:
- 112,275
- Stock #:
- 151-26
- VIN:
- 3FTTW8E91NRB02304
New arrival
2022 Ford Maverick
XL SuperCrew FWD
112,275 mi
Highland Park, IL
23 mi away
Great Deal
$14,749
- Year:
- 2021
- Make:
- GMC
- Model:
- Sierra 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 277 hp 3L I6 Diesel
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Diesel
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 88,719
- Stock #:
- 31-26448AA
- VIN:
- 1GTU9CET0MZ435405
2021 GMC Sierra 1500
Elevation Crew Cab 4WD
88,719 mi
Chesterton, IN
33 mi away
Great Deal
$28,192
- 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:
- Automatic
- Mileage:
- 62,222
- Stock #:
- P1443
- VIN:
- 3GCUYEED1MG235057
Price drop
-$1,320
2021 Chevrolet Silverado 1500
RST Crew Cab 4WD
62,222 mi
Michigan City, IN
40 mi away
Good Deal
$35,029
$33,709
- Year:
- 2023
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 310 hp 2.7L I4
- Exterior color:
- Northsky Blue Metallic
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 27,014
- Stock #:
- T24184
- VIN:
- 3GCPDKEK6PG134459
2023 Chevrolet Silverado 1500
LT Crew Cab 4WD
27,014 mi
Frankfort, IL
28 mi away
Fair Deal
$35,133
- 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:
- Bright White Clearcoat
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 63,667
- Stock #:
- 26285-1
- VIN:
- 1C6SRFJT2NN478884
2022 RAM 1500
Laramie Crew Cab 4WD
63,667 mi
North Aurora, IL
39 mi away
Good Deal
$33,728
- Year:
- 2023
- Make:
- Chevrolet
- Model:
- Colorado
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 310 hp 2.7L I4
- Exterior color:
- Glacier Blue
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 53,337
- Stock #:
- M8179
- VIN:
- 1GCPTEEKXP1163188
2023 Chevrolet Colorado
Trail Boss Crew Cab 4WD
53,337 mi
Crystal Lake, IL
42 mi away
Fair Deal
$34,155
- Year:
- 2023
- Make:
- Chevrolet
- Model:
- Silverado 1500
- 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
- Transmission:
- 8-Speed Automatic
- Mileage:
- 23,848
- Stock #:
- C31188
- VIN:
- 1GCRDAEK4PZ218928
New arrival
2023 Chevrolet Silverado 1500
Work Truck Double Cab 4WD
23,848 mi
Glen Ellyn, IL
23 mi away
Good Deal
$28,627
- Year:
- 2022
- Make:
- Nissan
- Model:
- Frontier
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 310 hp 3.8L V6
- Exterior color:
- Super Black
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray (Steel)
- Transmission:
- 9-Speed Automatic
- Mileage:
- 56,588
- Stock #:
- T4034A
- VIN:
- 1N6ED1EK2NN642785
2022 Nissan Frontier
PRO-4X Crew Cab 4WD
56,588 mi
Merrillville, IN
27 mi away
Fair Deal
$29,930
- 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
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 38,983
- Stock #:
- P1449
- VIN:
- 1GCUYGED9NZ198126
Price drop
-$1,000
2022 Chevrolet Silverado 1500
LTZ Crew Cab 4WD
38,983 mi
Crystal Lake, IL
43 mi away
Good Deal
$40,408
$39,408
- 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:
- Crystal Metallic
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 67,596
- Stock #:
- D1071A
- VIN:
- 1C6SRFFT3NN458023
2022 RAM 1500
Big Horn Crew Cab 4WD
67,596 mi
Crystal Lake, IL
43 mi away
Great Deal
$29,812
- 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:
- Red Hot
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 38,958
- Stock #:
- L62121A
- VIN:
- 3GCPDFEK5NG600368
New arrival
2022 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
38,958 mi
Lansing, IL
22 mi away
Fair Deal
$39,109
- Year:
- 2023
- 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:
- 13,595
- Stock #:
- E8489A
- VIN:
- 1C6JJTAMXPL593712
2023 Jeep Gladiator
Sport S Crew Cab 4WD
13,595 mi
Skokie, IL
11 mi away
Fair Deal
$37,000
- Year:
- 2021
- Make:
- Ford
- Model:
- F-150
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 400 hp 3.5L V6
- Exterior color:
- White
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- Medium Dark Slate
- Transmission:
- Automatic
- Mileage:
- 151,809
- Stock #:
- 4782
- VIN:
- 1FTFX1E80MKD26451
2021 Ford F-150
XL SuperCab LB 4WD
151,809 mi
Chicago, IL
7 mi away
Good Deal
$16,408
- 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:
- Sterling Metallic
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black/Timber
- Transmission:
- 8-Speed Automatic
- Mileage:
- 39,580
- Stock #:
- P4460
- VIN:
- 1GTP6DEK3P1151711
2023 GMC Canyon
AT4 Crew Cab 4WD
39,580 mi
Countryside, IL
14 mi away
Fair Deal
$37,192
- Year:
- 2021
- Make:
- RAM
- Model:
- 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 395 hp 5.7L V8
- Exterior color:
- Billet Silver Metallic Clearcoat
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 99,584
- Stock #:
- U10532
- VIN:
- 1C6SRFJT7MN815337
Price drop
-$1,277
2021 RAM 1500
Laramie Crew Cab 4WD
99,584 mi
Valparaiso, IN
40 mi away
Good Deal
$29,538
$28,261
- Year:
- 2021
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 4.3L V6 Flex Fuel Vehicle
- Exterior color:
- Shadow Gray Metallic
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Flex Fuel Vehicle
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 58,469
- Stock #:
- L61919A
- VIN:
- 1GCRYBEH5MZ153730
2021 Chevrolet Silverado 1500
Custom Double Cab 4WD
58,469 mi
Lansing, IL
22 mi away
Good Deal
$27,720
- Year:
- 2023
- Make:
- Ford
- Model:
- F-150
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 400 hp 3.5L V6
- Exterior color:
- Black
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 50,448
- Stock #:
- V2827
- VIN:
- 1FTEW1E85PFB01311
Sponsored Listing
2023 Ford F-150
Tremor SuperCrew 4WD
50,448 mi
Huntley, IL
45 mi away
Great Deal
$43,857
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