Used Chevrolet Silverado 1500 Custom Trail Boss for Sale near Chester, IL
185 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- Year:
- 2026
- 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:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black Cloth
- Transmission:
- Automatic
- Mileage:
- 4,177
- Stock #:
- T260856A
- VIN:
- 3GCPKCEK6TG127131
Sponsored by George Weber Chevrolet Columbia
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
4,177 mi
Columbia, IL
44 mi away
Good Deal
$44,077
- 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
- Transmission:
- Automatic
- Mileage:
- 119,375
- Stock #:
- 6111001
- VIN:
- 3GCPYCEK8NG184464
Sponsored Listing
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
119,375 mi
Saint Louis, MO
49 mi away
Good Deal
$26,099
- 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
- Transmission:
- Automatic
- Mileage:
- 58,728
- Stock #:
- 4231B
- VIN:
- 1GCPYCEL4MZ341639
Price drop
-$942
Sponsored Listing
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
58,728 mi
New Athens, IL
28 mi away
Good Deal
$35,137
$34,195
- 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 Gba
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 54,776
- Stock #:
- 7751A
- VIN:
- 3GCPDCED0NG679819
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
54,776 mi
Warrenton, MO
93 mi away
Good Deal
$34,895
- 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
- Transmission:
- Automatic
- Mileage:
- 58,728
- Stock #:
- 4231B
- VIN:
- 1GCPYCEL4MZ341639
Price drop
-$942
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
58,728 mi
New Athens, IL
28 mi away
Good Deal
$35,137
$34,195
- 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
- Transmission:
- Automatic
- Mileage:
- 119,375
- Stock #:
- 6111001
- VIN:
- 3GCPYCEK8NG184464
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
119,375 mi
Saint Louis, MO
49 mi away
Good Deal
$26,099
- 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 Gray
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 8,551
- Stock #:
- T21455B
- VIN:
- 3GCPKCEK3SG339841
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
8,551 mi
Creve Coeur, MO
62 mi away
Great Deal
$38,818
- 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
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic
- Mileage:
- 63,297
- Stock #:
- 270102
- VIN:
- 1GCPYCEF8MZ270102
New arrival
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
63,297 mi
Home delivery from Bend, OR
Price includes $3,356 shipping
Fair Deal
$33,319
- 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:
- Red Hot
- Combined gas mileage:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 118,282
- Stock #:
- P36312B
- VIN:
- 1GCPYCEF1MZ206855
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
118,282 mi
Home delivery from Memphis, TN
Free home delivery
Fair Deal
$28,251
- 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:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black Cloth
- Transmission:
- Automatic
- Mileage:
- 91,713
- Stock #:
- E1003
- VIN:
- 1GCPYCEF3KZ250322
Price drop
-$1,346
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
91,713 mi
Hazelwood, MO
66 mi away
Fair Deal
$29,114
$27,768
- 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, Cloth Seat Trim
- Transmission:
- Automatic
- Mileage:
- 8,679
- Stock #:
- 16677P
- VIN:
- 3GCUDCED2PG295840
Price drop
-$3,045
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
8,679 mi
O'Fallon, IL
47 mi away
Good Deal
$45,192
$42,524
- 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:
- SAND DUNE METALLIC
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 98,341
- Stock #:
- DN680533
- VIN:
- 3GCPDCED9NG680533
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
98,341 mi
Home delivery from Houston, TX
Price includes $589 shipping
Good Deal
$31,074
- 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:
- Glacier Blue Metallic
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 30,723
- Stock #:
- CC2036
- VIN:
- 3GCPDCEK8RG179394
Price drop
-$1,259
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
30,723 mi
Home delivery from Avon, IN
Price includes $338 shipping
Good Deal
$38,944
$37,944
- 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:
- Red Hot
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 26,397
- Stock #:
- 69928A
- VIN:
- 3GCPDCEK2RG437988
Price drop
-$1,599
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
26,397 mi
Home delivery from Mountain Grove, MO
Free home delivery
Good Deal
$40,000
$38,500
- 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:
- Gray
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic
- Mileage:
- 90,269
- Stock #:
- 12-5041
- VIN:
- 1GCPYCEF9KZ342034
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
90,269 mi
Home delivery from El Paso, IL
Price includes $298 shipping
Good Deal
$27,648
- 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:
- Black
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic Overdrive
- Mileage:
- 46,820
- Stock #:
- 16017
- VIN:
- 3GCPKCEKXSG328917
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
46,820 mi
Home delivery from Smithfield, NC
Price includes $1,320 shipping
Fair Deal
$39,419
- 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:
- [GA0] Northsky Blue Metallic
- Combined gas mileage:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 68,980
- Stock #:
- TP26672
- VIN:
- 1GCPYCEF5MZ257887
![[GA0] Northsky Blue Metallic 2021 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic](https://static.cargurus.com/images/forsale/2026/09/25/02/53/2021_chevrolet_silverado_1500-pic-4528600746641468461-1024x768.jpeg?io=true&width=640&height=480&fit=bounds&format=jpg&auto=webp)
New arrival
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
68,980 mi
Ellisville, MO
63 mi away
Fair Deal
$32,928
- 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:
- Red Hot G7c
- Combined gas mileage:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black H1t
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 46,558
- Stock #:
- PHN1330A
- VIN:
- 1GCPYCEF0MZ243928
Price drop
-$1,199
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
46,558 mi
Park Hills, MO
36 mi away
Fair Deal
$35,965
$34,766
- 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:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 158,831
- Stock #:
- C17739A
- VIN:
- 3GCPYCEFXKG173285
Price drop
-$1,000
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
158,831 mi
Saint Peters, MO
74 mi away
Great Deal
$18,614
$17,614
- 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 Gray
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 22,503
- Stock #:
- P32548A
- VIN:
- 3GCPKCEK0SG355639
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
22,503 mi
Du Quoin, IL
33 mi away
Good Deal
$40,977
- 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:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 71,652
- Stock #:
- A88197
- VIN:
- 1GCPYCEF1MZ270913
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
71,652 mi
Herculaneum, MO
39 mi away
Fair Deal
$32,576
- Year:
- 2026
- 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
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 14,487
- Stock #:
- K26347A
- VIN:
- 3GCUKCED0TG122883
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
14,487 mi
Saint Louis, MO
57 mi away
Fair Deal
$46,950
- 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:
- Silver
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 64,044
- Stock #:
- 290751
- VIN:
- 1GCPYCEL5MZ290751
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
64,044 mi
Home delivery from Gallup, NM
Price includes $1,586 shipping
Fair Deal
$34,080
- 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:
- Cherry Red
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 50,370
- Stock #:
- A17166N
- VIN:
- 1GCPYCEL2NZ131123
Sponsored Listing
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
50,370 mi
Saint Charles, MO
72 mi away
Good Deal
$35,371
FAQs
How much does the Chevrolet Silverado 1500 Custom Trail Boss cost in Chester, IL?
The average Chevrolet Silverado 1500 Custom Trail Boss costs about $26,290.88. The average price has decreased by -3.4% since last year. The 165 for sale near Chester, IL on CarGurus, range from $20,959 to $63,840 in price.
How many Chevrolet Silverado 1500 Custom Trail Boss vehicles in Chester, IL have no reported accidents or damage?
161 out of 165 for sale near Chester, 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/MPGe.
What fuel types are available?
Diesel, Flex Fuel Vehicle, 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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