Used Chevrolet Silverado 1500 LT Trail Boss for Sale nearFreeport, IL
406 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- Year:
- 2023
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 3L I6 Diesel
- Exterior color:
- Sterling Gray Metallic
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Diesel
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 56,997
- Stock #:
- X6609
- VIN:
- 3GCUDFE82PG270439
Sponsored by Hawk Chrysler Jeep Dodge RAM
2023 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
56,997 mi
Forest Park, IL
98 mi away
Fair Deal
$42,845
- Year:
- 2024
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 3L I6 Diesel
- Exterior color:
- Dark Ash Metallic
- Combined gas mileage:
- 25 MPG
- Fuel type:
- Diesel
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 24,919
- Stock #:
- PC15753
- VIN:
- 3GCUDFE82RG302146
Sponsored Listing
2024 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
24,919 mi
Countryside, IL
98 mi away
Good Deal
$46,301
- 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:
- 83,645
- Stock #:
- 71997
- VIN:
- 3GCUDFED0NG672888
Sponsored Listing
2022 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
83,645 mi
Sun Prairie, WI
62 mi away
Fair Deal
$37,645
- 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:
- Northsky Blue Metallic
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 59,870
- Stock #:
- 72053
- VIN:
- 1GCPYFED0MZ332740
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
59,870 mi
Sun Prairie, WI
62 mi away
Fair Deal
$37,998
- 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:
- Summit White
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 65,777
- Stock #:
- P1847
- VIN:
- 3GCUDFED5RG159187
Price drop
-$2,000
2024 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
65,777 mi
Schaumburg, IL
83 mi away
Good Deal
$42,313
$40,313
- 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:
- 95,906
- Stock #:
- P17617A
- VIN:
- 1GCPYFED3KZ381671
2019 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
95,906 mi
Mukwonago, WI
77 mi away
Fair Deal
$30,122
- Year:
- 2025
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 355 hp 5.3L V8
- Exterior color:
- CYPRESS GRAY
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 12,519
- Stock #:
- K260630A
- VIN:
- 3GCUKFED4SG185386
New arrival
2025 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
12,519 mi
Kenosha, WI
88 mi away
Good Deal
$52,594
- 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:
- 55,270
- Stock #:
- D25307C
- VIN:
- 3GCPYFEDXKG229810
2019 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
55,270 mi
Davenport, IA
70 mi away
Fair Deal
$33,821
- Year:
- 2024
- 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
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 28,477
- Stock #:
- 22X769
- VIN:
- 3GCPDFEK9RG286181
Price drop
-$902
2024 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
28,477 mi
Platteville, WI
50 mi away
Great Deal
$39,395
$38,493
- 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:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 100,770
- Stock #:
- C20632PC
- VIN:
- 1GCPYFED0MZ197596
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
100,770 mi
Milwaukee, WI
96 mi away
Good Deal
$30,486
- 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:
- Radiant Red
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 47,584
- Stock #:
- 53873A
- VIN:
- 3GCUDFED6PG201833
2023 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
47,584 mi
Crystal Lake, IL
68 mi away
Fair Deal
$43,908
- 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:
- 48,637
- Stock #:
- F615659T
- VIN:
- 1GCPYFEDXMZ444316
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
48,637 mi
Stoughton, WI
46 mi away
Good Deal
$37,500
- 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:
- Sand Dune Metallic
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 50,157
- Stock #:
- P10769
- VIN:
- 3GCPDFEK4PG100026
2023 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
50,157 mi
Naperville, IL
83 mi away
Fair Deal
$39,388
- 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:
- Black
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 41,042
- Stock #:
- 26462A
- VIN:
- 1GCPYFED1LZ187318
2020 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
41,042 mi
St Charles, IL
74 mi away
Good Deal
$36,673
- 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:
- Gray (Satin Steel Metallic)
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 39,609
- Stock #:
- MK260615A
- VIN:
- 3GCPYFED6MG479144
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
39,609 mi
McHenry, IL
69 mi away
Good Deal
$38,030
- 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:
- Gray (Satin Steel Metallic)
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 58,708
- Stock #:
- TT67464B
- VIN:
- 1GCPYFED9LZ313439
2020 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
58,708 mi
Willowbrook, IL
95 mi away
Good Deal
$34,059
- 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:
- Sterling Gray Metallic
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 25,652
- Stock #:
- C15413A
- VIN:
- 3GCUDFED9RG454907
New arrival
2024 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
25,652 mi
Milwaukee, WI
93 mi away
Fair Deal
$49,897
- 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
2022 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
109,126 mi
Downers Grove, IL
89 mi away
Good Deal
$29,892
- 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:
- Glacier Blue Metallic
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black, Cloth Seat Trim
- Transmission:
- Automatic
- Mileage:
- 50,781
- Stock #:
- G261177A
- VIN:
- 3GCUDFED2NG674237
2022 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
50,781 mi
Home delivery from Sullivan, MO
Price includes $590 shipping
Great Deal
$39,205
- 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:
- Shadow Gray Metallic
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- JET BLACK, CLOTH SEAT TRIM
- Transmission:
- Automatic
- Mileage:
- 37,270
- Stock #:
- 42478A
- VIN:
- 1GCPYFED5MZ342390
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
37,270 mi
Baraboo, WI
82 mi away
Good Deal
$38,802
- 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, Cloth Seat Trim
- Transmission:
- Automatic
- Mileage:
- 77,481
- Stock #:
- GC26479A
- VIN:
- 1GCPYFED2NZ135876
New arrival
2022 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
77,481 mi
Home delivery from Sullivan, MO
Price includes $590 shipping
Good Deal
$35,205
- Year:
- 2025
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 420 hp 6.2L V8
- Exterior color:
- Summit White
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gideon/Very Dark Atmosphere
- Transmission:
- Automatic
- Mileage:
- 10,528
- Stock #:
- 1575233A
- VIN:
- 3GCUKFEL3SG322938
2025 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
10,528 mi
Home delivery from Jackson, TN
Price includes $1,150 shipping
Fair Deal
$57,707
- Year:
- 2021
- 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 (Satin Steel Metallic)
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 90,088
- Stock #:
- TE144341B
- VIN:
- 3GCPYFEL6MG475053
Price drop
-$1,723
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
90,088 mi
Bristol, WI
87 mi away
Good Deal
$33,487
$31,764
- 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:
- Northsky Blue Metallic
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gideon/Very Dark Atmosphere
- Transmission:
- Automatic
- Mileage:
- 56,924
- Stock #:
- 34334U
- VIN:
- 3GCUDFED7PG231505
Sponsored Listing
2023 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
56,924 mi
Channahon, IL
95 mi away
Fair Deal
$42,800
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 $20,954.00 to $73,996.75 with an average price of $29,173.47. 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
*CarGurus meticulously monitors the prices of millions of pre-owned vehicle listings, offering users precise and up-to-date market insights. Historical pricing data excludes any additional dealer fees as of May 3, 2026.
FAQs
How much does the Chevrolet Silverado 1500 LT Trail Boss cost in Freeport, IL?
The average Chevrolet Silverado 1500 LT Trail Boss costs about $26,586.15. The average price has decreased by -1.7% since last year. The 306 for sale near Freeport, IL on CarGurus, range from $20,954 to $73,997 in price.
How many Chevrolet Silverado 1500 LT Trail Boss vehicles in Freeport, IL have no reported accidents or damage?
261 out of 306 for sale near Freeport, IL have no reported accidents or damage.
What is the fuel economy of the Chevrolet Silverado 1500 LT Trail Boss?
Depending on the engine and options, the Chevrolet Silverado 1500 LT Trail Boss gets between 15 and 24 MPG/MPGe.
What fuel types are available?
Diesel, Gasoline engines are available.
*CarGurus meticulously monitors the prices of millions of pre-owned vehicle listings, offering users precise and up-to-date market insights. Historical pricing data excludes any additional dealer fees as of May 3, 2026.
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