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Used Chevrolet Silverado 1500 Custom Trail Boss for Sale near Roscoe, IL

145 results

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:
Summit White
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
42,295
Stock #:
56035A
VIN:
3GCPDCEK3RG216626
Summit White 2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive Automatic
Advantage Chevrolet Hodgkins

Sponsored by Advantage Chevrolet Hodgkins

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

42,295 mi

Hodgkins, IL
73 mi away
Good Deal
Manufacturer certified

$38,036

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:
51,083
Stock #:
48816
VIN:
3GCPDCEK7PG361519
Summit White 2023 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 8-Speed Automatic

Sponsored Listing

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

51,083 mi

Frankfort, IL
86 mi away
Fair Deal
Third-party certified

$36,995

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:
45,678
Stock #:
P6036
VIN:
3GCUDCED1PG323353
Summit White 2023 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive Automatic

Sponsored Listing

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

45,678 mi

Elmhurst, IL
63 mi away
Good Deal

$38,992

Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Red Hot
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
58,290
Stock #:
P1836
VIN:
3GCPYCEK8NG208262
Red Hot 2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 8-Speed Automatic
Price drop

-$1,350

 

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

58,290 mi

Schaumburg, IL
54 mi away
Good Deal

$34,163

$32,813

Year:
2025
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
310 hp 2.7L I4
Exterior color:
Cypress
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
20,860
Stock #:
50003A
VIN:
3GCPKCEK1SG296827
Cypress 2025 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 8-Speed Automatic

 

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

20,860 mi

Fox Lake, IL
41 mi away
Good Deal
Manufacturer certified

$42,110

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:
Red
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
77,138
Stock #:
06T4114A
VIN:
1GCRYCEF0KZ299664
Red 2019 Chevrolet Silverado 1500 Custom Trail Boss Double Cab 4WD Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive
New arrival

 

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

77,138 mi

Elkhorn, WI
30 mi away
Good Deal

$28,637

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:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
33,030
Stock #:
56183A
VIN:
1GCPYCEF3LZ190768
Black 2020 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive Automatic
New arrival

 

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

33,030 mi

Hodgkins, IL
73 mi away
Great Deal

$34,118

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:
Red Hot
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
14,080
Stock #:
26RL211A
VIN:
3GCUDCED3RG316519
Red Hot 2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive Automatic

 

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

14,080 mi

Janesville, WI
21 mi away
Fair Deal

$45,316

Year:
2019
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:
White
Combined gas mileage:
17 MPG
Fuel type:
Flex Fuel Vehicle
Interior color:
Black
Transmission:
Automatic
Mileage:
67,825
Stock #:
G293416
VIN:
3GCPYCEH5KG293416
White 2019 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive Automatic

 

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

67,825 mi

Home delivery from West Palm Beach, FL
Price includes $1,798 shipping
Great Deal

$27,692

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:
Shadow Gray Metallic
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
114,828
Stock #:
02X1151A
VIN:
3GCPYCEF6LG184849
Shadow Gray Metallic 2020 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive
New arrival

 

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

114,828 mi

Delavan, WI
23 mi away
Fair Deal

$27,545

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:
16 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
110,080
Stock #:
935390B
VIN:
1GCPYCEF5KZ366976
Black 2019 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive

 

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

110,080 mi

Maquoketa, IA
89 mi away
Fair Deal

$26,490

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:
16 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
85,808
Stock #:
16044
VIN:
1GCRYCEF3KZ315436
Black 2019 Chevrolet Silverado 1500 Custom Trail Boss Double Cab 4WD Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive

 

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

85,808 mi

Home delivery from Dayton, OH
Price includes $465 shipping
Fair Deal

$27,911

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
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
55,339
Stock #:
MX4446
VIN:
1GCPYCEL1MZ352307
Gray 2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive Automatic
New arrival

 

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

55,339 mi

Home delivery from Louisville, TN
Price includes $949 shipping
Good Deal

$35,425

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:
Black
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
94,925
Stock #:
W0237
VIN:
1GCPYCEL0MZ347549
Black 2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive Automatic

 

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

94,925 mi

Whitewater, WI
31 mi away
Good Deal
Manufacturer certified

$30,000

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:
45,678
Stock #:
P6036
VIN:
3GCUDCED1PG323353
Summit White 2023 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive Automatic

 

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

45,678 mi

Elmhurst, IL
63 mi away
Good Deal

$38,992

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:
16 MPG
Fuel type:
Gasoline
Transmission:
6-Speed Automatic Overdrive
Mileage:
84,839
Stock #:
MX4469
VIN:
1GCPYCEF2LZ149662
Black 2020 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive

 

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

84,839 mi

Home delivery from Louisville, TN
Price includes $949 shipping
Fair Deal

$30,425

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:
Sterling Gray Metallic
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
20,075
Stock #:
260201A
VIN:
3GCPDCEK6RG209699
Sterling Gray Metallic 2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 8-Speed Automatic

 

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

20,075 mi

Joliet, IL
76 mi away
Good Deal

$40,220

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:
16 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
171,876
Stock #:
A530A
VIN:
1GCPYCEFXLZ104226
Black 2020 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive
Price drop

-$500

 

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

171,876 mi

Dwight, IL
96 mi away
Good Deal

$20,865

$20,365

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:
Black
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
41,920
Stock #:
Q11973
VIN:
3GCUDCED7PG127837
Black 2023 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive Automatic

 

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

41,920 mi

Dubuque, IA
88 mi away
Fair Deal

$40,280

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:
8-Speed Automatic
Mileage:
71,526
Stock #:
53595
VIN:
1GCPYCEK6NZ234598
Northsky Blue Metallic 2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 8-Speed Automatic

 

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

71,526 mi

Home delivery from Cambridge, OH
Price includes $314 shipping
Good Deal

$30,240

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:
Dark Ash Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
63,642
Stock #:
G2658A
VIN:
3GCPDCED4NG663283
Dark Ash Metallic 2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive Automatic

 

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

63,642 mi

Grayslake, IL
50 mi away
Fair Deal

$36,653

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:
Red
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
50,584
Stock #:
2351
VIN:
1GCRYCEF8KZ262636
Red 2019 Chevrolet Silverado 1500 Custom Trail Boss Double Cab 4WD Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive
New arrival

 

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

50,584 mi

Milton, WI
24 mi away
Fair Deal

$32,388

Year:
2025
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
310 hp 2.7L I4
Exterior color:
Cypress
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
20,860
Stock #:
50003A
VIN:
3GCPKCEK1SG296827
Cypress 2025 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 8-Speed Automatic

Sponsored Listing

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

20,860 mi

Fox Lake, IL
41 mi away
Good Deal
Manufacturer certified

$42,110

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FAQs

How much does the Chevrolet Silverado 1500 Custom Trail Boss cost in Roscoe, IL?
The average Chevrolet Silverado 1500 Custom Trail Boss costs about $27,269.71. The average price has decreased by -2% since last year. The 120 for sale near Roscoe, IL on CarGurus, range from $18,828 to $65,687 in price.
How many Chevrolet Silverado 1500 Custom Trail Boss vehicles in Roscoe, IL have no reported accidents or damage?
120 out of 120 for sale near Roscoe, IL have no reported accidents or damage.
What is the fuel economy of the Chevrolet Silverado 1500 Custom Trail Boss?
Depending on the engine and options, the Chevrolet Silverado 1500 Custom Trail Boss gets between 15 and 24 MPG (or EV battery range).
What fuel types are available?
Diesel, Flex Fuel Vehicle, Gasoline engines are available.

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