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Used Chevrolet Silverado 1500 LT Trail Boss for Sale nearSimpson, IL

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325 vehicles found

Year:
2020
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Blue
Fuel type:
Gasoline
Interior color:
Black
Mileage:
125,122
Stock #:
440195
VIN:
3GCPYFED6LG440195
Blue 2020 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive
Hall Family Autos

Sponsored by Hall Family Autos

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

125,122 mi

Maceo, KY
100 mi away
Fair Deal

$29,898

Year:
2026
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
420 hp 6.2L V8
Exterior color:
Gray
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Brown (Beige)
Transmission:
Automatic
Mileage:
2,935
Stock #:
14054B
VIN:
3GCUKFEL3TG112194
Gray 2026 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

Sponsored Listing

2026 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

2,935 mi

Martin, TN
79 mi away
Good Deal

$59,651

Year:
2026
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
3L I6 Diesel
Exterior color:
Cypress Gray
Combined gas mileage:
22 MPG
Fuel type:
Diesel
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
9,113
Stock #:
118060P
VIN:
3GCUKFE87TG118060
Cypress Gray 2026 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

Sponsored Listing

2026 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

9,113 mi

Paducah, KY
27 mi away
Fair Deal

$61,208

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:
Oxford Brown Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
51,942
Stock #:
TA6227A
VIN:
1GCPYFED8MZ388019
Oxford Brown Metallic 2021 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

51,942 mi

Home delivery from Ottawa, IL
Price includes $271 shipping
Good Deal

$36,981

Year:
2020
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Blue
Fuel type:
Gasoline
Interior color:
Black
Mileage:
59,616
Stock #:
154469
VIN:
1GCPYFED0LZ154469
Blue 2020 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive
Price drop

-$800

 

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

59,616 mi

Home delivery from Brownsville, TN
Price includes $165 shipping
Great Deal

$33,464

$32,664

Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Black
Interior color:
Black
Transmission:
Automatic
Mileage:
83,685
Stock #:
227612
VIN:
1GCUYFET9NZ227612
Black 2022 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

83,685 mi

Home delivery from Baton Rouge, LA
Price includes $646 shipping
Good Deal

$35,570

Year:
2024
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Radiant Red Tintcoat
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
82,008
Stock #:
C1617A
VIN:
3GCUDFED2RG292019

 

2024 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

82,008 mi

Mayfield, KY
48 mi away
Great Deal

$39,485

Year:
2019
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:
8-Speed Automatic
Mileage:
61,105
Stock #:
P5367B
VIN:
3GCPYFEDXKG119629
Black 2019 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 8-Speed Automatic

 

2019 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

61,105 mi

Home delivery from Monroe, WI
Price includes $359 shipping
Good Deal

$33,272

Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Black
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
53,000
Stock #:
A319266A
VIN:
3GCPYFED5NG192590
Black 2022 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

53,000 mi

Home delivery from Pueblo, CO
Price includes $1,305 shipping
Fair Deal

$39,990

Year:
2024
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Slate Gray Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
41,586
Stock #:
NT26107A
VIN:
3GCUDFED6RG237752
Slate Gray Metallic 2024 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2024 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

41,586 mi

Home delivery from Delphos, OH
Price includes $411 shipping
Good Deal

$46,336

Year:
2019
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Shadow Gray Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
99,026
Stock #:
P94806A
VIN:
1GCPYFED6KZ426800
Shadow Gray Metallic 2019 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 8-Speed Automatic
Price drop

-$2,500

 

2019 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

99,026 mi

Home delivery from Columbia, TN
Price includes $236 shipping
Good Deal

$31,734

$29,234

Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Northsky Blue Metallic
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
47,877
Stock #:
53757
VIN:
1GCPYFED6NZ106347
Northsky Blue Metallic 2022 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

47,877 mi

Home delivery from Cambridge, OH
Price includes $316 shipping
Good Deal

$38,314

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:
Summit White
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Gideon/Very Dark Atmosphere
Transmission:
Automatic
Mileage:
94,251
Stock #:
P5104
VIN:
3GCPYFEDXMG101876
Summit White 2021 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic
Price drop

-$1,000

 

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

94,251 mi

Home delivery from Washington, PA
Price includes $1,715 shipping
Great Deal

$32,155

$31,155

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:
Silver Ice Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
77,705
Stock #:
X5410A
VIN:
1GCPYFED2MZ422830
Silver Ice Metallic 2021 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

77,705 mi

Home delivery from Palmyra, IL
Free home delivery
Great Deal

$33,695

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:
69,548
Stock #:
F277578P
VIN:
3GCUDFED0PG277578
Sterling Gray Metallic 2023 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic
Price drop

-$2,120

 

2023 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

69,548 mi

Home delivery from Trumann, AR
Price includes $248 shipping
Good Deal

$41,376

$39,256

Year:
2020
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Silver Ice Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
90,358
Stock #:
G26204A
VIN:
3GCPYFED5LG241641
Silver Ice Metallic 2020 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

90,358 mi

Paducah, KY
27 mi away
Good Deal
Manufacturer certified

$33,094

Year:
2020
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:
57,637
Stock #:
G261028A
VIN:
3GCPYFED3LG158841
Summit White 2020 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

57,637 mi

Home delivery from Sullivan, MO
Price includes $210 shipping
Fair Deal
Manufacturer certified

$36,704

Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Shadow Gray Metallic
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
109,126
Stock #:
N260273A
VIN:
1GCPYFED9NZ156241
Shadow Gray Metallic 2022 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

109,126 mi

Home delivery from Downers Grove, IL
Price includes $606 shipping
Good Deal

$31,041

Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Summit White
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
41,648
Stock #:
PM238331
VIN:
1GCPYFEL5NZ238331
Summit White 2022 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

41,648 mi

Home delivery from Pleasantville, NJ
Price includes $1,490 shipping
Great Deal

$38,380

Year:
2020
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Red Hot
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
156,810
Stock #:
A26C64B
VIN:
1GCPYFED7LZ365961
Red Hot 2020 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic
New arrival

 

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

156,810 mi

Home delivery from Pomeroy, OH
Price includes $1,131 shipping
Fair Deal

$24,019

Year:
2023
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
420 hp 6.2L V8
Exterior color:
White (Iridescent Pearl Tricoat)
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
55,432
Stock #:
T1153459B
VIN:
3GCUDFEL4PG319659
White (Iridescent Pearl Tricoat) 2023 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic
New arrival

 

2023 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

55,432 mi

Home delivery from Franklin, TN
Price includes $225 shipping
Fair Deal

$46,101

Year:
2023
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
3L I6 Diesel
Exterior color:
Gray
Combined gas mileage:
24 MPG
Fuel type:
Diesel
Interior color:
Black
Transmission:
Automatic
Mileage:
75,314
Stock #:
G115624
VIN:
3GCUDFE81PG115624
Gray 2023 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2023 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

75,314 mi

Home delivery from Houston, TX
Price includes $998 shipping
Great Deal

$37,720

Year:
2024
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
White
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
82,685
Stock #:
283572
VIN:
3GCUDFED3RG283572
White 2024 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic
New arrival

 

2024 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

82,685 mi

Home delivery from Gallup, NM
Price includes $1,680 shipping
Good Deal

$40,674

Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Summit White
Interior color:
Black
Transmission:
Automatic
Mileage:
94,593
Stock #:
100231M
VIN:
3GCPYFED1NG100231
Summit White 2022 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic
New arrival

Sponsored Listing

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

94,593 mi

Mayfield, KY
48 mi away
Fair Deal

$35,566

Overview

The Chevrolet Silverado 1500 LT Trail Boss is only available from in two body configurations: the Crew Cab Short Bed and the Crew Cab Standard Bed. As the “Trail Boss” name suggests, this trim is only available in four-wheel drive. From there, the powertrain options get a little dizzying. You have four engines to choose from: The 2.7-liter turbocharged four-cylinder, the 5.3-liter EcoTec V-8, the 3.0-liter Duramax Turbo Diesel inline six, and the 6.2-liter EcoTec V-8. The four-cylinder turbo is the only one available with an eight-speed automatic transmission. All of the other engines require the 10-speed automatic.

Key Features

  • Standard 355hp 5.3-liter V-8 standard, standard 10-speed automatic transmission
  • Two-inch factory suspension lift, 18-inch gloss black wheels, Goodyear Wrangler Duratrac tires, raised hood and styled insert
  • Leather-wrapped wheel, remote start, all-weather floor liners, 40/20/40 split bench seat, dual-zone climate control, 10-way power driver’s seat, heated front seats, heated wheel
  • 13.4-inch color touchscreen display, 12.3-inch multicolor, reconfigurable Driver Information Center, 6-speaker audio, WiFi hot spot, Wireless Apple CarPlay/Android Auto

Pricing Details

The Chevrolet Silverado LT Trail Boss has a base MSRP of $57,095 with the turbocharged four-cylinder. Used examples on CarGurus range from $22,064.00 to $75,389.45 with an average price of $30,253.34. The 5.3-liter V-8 adds $2,315, the diesel engine adds $3,130 and the 6.2-liter V-8 adds $4,460. There are nine different option packages, ranging from $325 for the Dark Essentials Package, to the $3,685 LT Trail Boss Premium Package, which includes Convenience Package II, Safety Package, Bed Protection Package, a power up and down tailgate and leather upholstery.

Specifications

Performance

  • Engine

    355hp 5.3-liter V8

  • Transmission

    10-speed automatic

  • Drivetrain

    Four-wheel drive

  • Horsepower/Torque

    355hp/383 lb-ft

  • 0-60 mph

    15.1 seconds (estimated)

  • MPG

    15 mpg city, 19 highway, 16 combined

  • Curb weight

    5,130 pounds

Dimensions

  • wheelbase

    147.4 inches

  • length

    231.9 inches

  • width

    81.2 inches

  • height

    75.5 inches

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