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Used Chevrolet Silverado 1500 LT Trail Boss for Sale near Naperville, IL

324 results
Naperville, IL
2024 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD Elgin Volkswagen

2024 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

65,509 miles

$40,133

Good Deal
Elgin, IL
19 mi away
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:
65,509
Stock number:
P2893
VIN:
3GCUDFED5RG159187

Sponsored

2019 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2019 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

78,388 miles

$31,795

Fair Deal
Certified Pre-Owned
Melrose Park, IL
17 mi away
Year:
2019
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Transmission:
8-Speed Automatic
Mileage:
78,388
Stock number:
P23784A
VIN:
1GCPYFED4KZ133980

Sponsored

2022 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

68,199 miles

$33,789

Great Deal
Gurnee, IL
43 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
White
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
68,199
Stock number:
GM30035
VIN:
1GCPYFED1NZ172840

Sponsored

2024 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2024 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

65,509 miles

$40,133

Good Deal
Elgin, IL
19 mi away
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:
65,509
Stock number:
P2893
VIN:
3GCUDFED5RG159187

2021 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

62,357 miles

$35,972

Good Deal
Bolingbrook, IL
8 mi away
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:
Summit White
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
62,357
Stock number:
49459B
VIN:
3GCPYFEL8MG454706

2021 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

15,366 miles

$40,700

Good Deal
Merrillville, IN
47 mi away
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:
Black
Transmission:
Automatic
Mileage:
15,366
Stock number:
P1099
VIN:
3GCPYFEDXMG434773

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

72,708 miles

$33,400

Good Deal
Westmont, IL
10 mi away
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:
72,708
Stock number:
D3373B
VIN:
1GCPYFED9MZ169568

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Photos coming soon

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

35,321 miles

$38,495

Good Deal
Certified Pre-Owned
Bridgeview, IL
18 mi away
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:
35,321
Stock number:
JP2804
VIN:
1GCPYFEL1NZ156676

Preparing for a close up...

Photos coming soon

2025 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

10,730 miles

$53,999

Good Deal
Certified Pre-Owned
Naperville, IL
3 mi away
Year:
2025
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:
23 MPG
Fuel type:
Diesel
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
10,730
Stock number:
K6987
VIN:
3GCUKFE89SG246184

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Photos coming soon

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

23,579 miles

$46,972

Fair Deal
Certified Pre-Owned
Bolingbrook, IL
8 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:
Northsky Blue Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
23,579
Stock number:
P15836
VIN:
3GCUDFED4NG617117

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Photos coming soon

2019 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

58,637 miles

$34,500

Fair Deal
Minooka, IL
23 mi away
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:
Black
Transmission:
8-Speed Automatic
Mileage:
58,637
Stock number:
KZ126138
VIN:
1GCPYFED4KZ126138

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

93,820 miles

$30,995

Fair Deal
Bourbonnais, IL
46 mi away
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:
Summit White
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
93,820
Stock number:
B5355D
VIN:
1GCPYFED1KZ155449

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

19,520 miles

$40,897

Good Deal
Store transfer to Naperville, IL
1,725 mi away • Price includes $1,899 shipping Price includes $1,899 shipping
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Blue
Interior color:
Black
Transmission:
Automatic
Mileage:
19,520
Stock number:
26433898
VIN:
1GCPYFEL0NZ228094

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

78,388 miles

$31,795

Fair Deal
Certified Pre-Owned
Melrose Park, IL
17 mi away
Year:
2019
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Transmission:
8-Speed Automatic
Mileage:
78,388
Stock number:
P23784A
VIN:
1GCPYFED4KZ133980

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

62,894 miles

$39,885

Good Deal
Sycamore, IL
32 mi away
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:
62,894
Stock number:
39P1495
VIN:
3GCUDFED3PG338731

Sponsored

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