Used Chevrolet Silverado 1500 Custom Trail Boss for Sale nearGary, IN
179 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- 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:
- Silver
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 53,151
- Stock #:
- 21221169T
- VIN:
- 1GCPYCEL5NZ221169
Price drop
-$1,005
Sponsored by Garber Chevrolet Highland
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
53,151 mi
Highland, IN
8 mi away
Fair Deal
$36,173
$35,420
- 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:
- Slate Gray Metallic
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 32,122
- Stock #:
- 34-1577P
- VIN:
- 3GCUKCED0SG119948
Price drop
-$2,892
Sponsored Listing
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
32,122 mi
Burns Harbor, IN
12 mi away
Good Deal
$43,171
$40,279
- 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
- Combined gas mileage:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 32,267
- Stock #:
- T289222
- VIN:
- 1GCPYCEF3MZ289222
Sponsored Listing
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
32,267 mi
Bensenville, IL
39 mi away
Fair Deal
$36,155
- Year:
- 2021
- 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:
- Gray
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Flex Fuel Vehicle
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 44,878
- Stock #:
- C21235704A
- VIN:
- 1GCPYCEH0MZ416235
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
44,878 mi
Downers Grove, IL
38 mi away
Good Deal
$32,597
- 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
- Combined gas mileage:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 51,103
- Stock #:
- 26582A
- VIN:
- 1GCPYCEF3MZ403056
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
51,103 mi
Peotone, IL
29 mi away
Fair Deal
$33,413
- 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:
- Silver
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 53,151
- Stock #:
- 21221169T
- VIN:
- 1GCPYCEL5NZ221169
Price drop
-$1,005
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
53,151 mi
Highland, IN
8 mi away
Fair Deal
$36,173
$35,420
- 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:
- Dark Ash Metallic
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 35,517
- Stock #:
- T24279
- VIN:
- 3GCPDCEK8RG210174
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
35,517 mi
Frankfort, IL
27 mi away
Fair Deal
$37,862
- Year:
- 2021
- 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:
- Silver Ice Metallic
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Flex Fuel Vehicle
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 123,060
- Stock #:
- P7863B
- VIN:
- 1GCPYCEH3MZ445535
Price drop
-$1,101
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
123,060 mi
Schaumburg, IL
47 mi away
Fair Deal
$25,401
$24,300
- 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:
- Gray
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 59,358
- Stock #:
- C9N193663
- VIN:
- 3GCPDCEK2RG193663
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
59,358 mi
Valparaiso, IN
16 mi away
Fair Deal
$36,521
- Year:
- 2021
- 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:
- Gray
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Flex Fuel Vehicle
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 82,085
- Stock #:
- 13222
- VIN:
- 1GCPYCEH1MZ215802
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
82,085 mi
Frankfort, IL
26 mi away
Good Deal
$27,972
- 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:
- Dark Ash Metallic
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 12,940
- Stock #:
- C260682A
- VIN:
- 3GCUDCED5RG267775
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
12,940 mi
Schaumburg, IL
48 mi away
Good Deal
$42,213
- 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
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 108,266
- Stock #:
- 13271
- VIN:
- 1GCPYCEF6LZ106538
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
108,266 mi
Frankfort, IL
26 mi away
Good Deal
$24,374
- 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:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 41,657
- Stock #:
- 20325
- VIN:
- 1GCPYCEF4MZ289181
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
41,657 mi
Home delivery from Mesa, AZ
Price includes $1,447 shipping
Fair Deal
$35,442
- 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 $1,838 shipping
Fair Deal
$34,332
- 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
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
63,297 mi
Home delivery from Bend, OR
Price includes $3,424 shipping
Fair Deal
$33,387
- 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:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 70,535
- Stock #:
- F4957A
- VIN:
- 1GCPYCEFXMZ273292
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
70,535 mi
Home delivery from Saint Charles, IL
Price includes $400 shipping
Fair Deal
$32,147
- 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:
- Glacier Blue Metallic
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 52,070
- Stock #:
- 70109A
- VIN:
- 3GCPDCEK8PG284157
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
52,070 mi
Frankfort, IL
27 mi away
Good Deal
$35,373
- 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:
- JET BLACK
- Transmission:
- Automatic
- Mileage:
- 11,352
- Stock #:
- 277668A
- VIN:
- 3GCPKCEK7SG347277
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
11,352 mi
Home delivery from Madison, WI
Price includes $145 shipping
Fair Deal
$43,360
- 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
- Combined gas mileage:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 42,114
- Stock #:
- MG311737
- VIN:
- 3GCPYCEF5MG311737
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
42,114 mi
Home delivery from Corsicana, TX
Price includes $1,239 shipping
Good Deal
$33,055
- 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
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic
- Mileage:
- 59,379
- Stock #:
- 12-5216
- VIN:
- 1GCPYCEF6MZ428419
New arrival
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
59,379 mi
Home delivery from El Paso, IL
Price includes $159 shipping
Fair Deal
$34,047
- 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:
- 6-Speed Automatic Overdrive
- Mileage:
- 95,901
- Stock #:
- 110261TK
- VIN:
- 1GCPYCEF9LZ110261
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
95,901 mi
Home delivery from Noblesville, IN
Price includes $194 shipping
Good Deal
$25,236
- 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
- Combined gas mileage:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 84,249
- Stock #:
- GM31867T
- VIN:
- 1GCPYCEF6MZ370442
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
84,249 mi
Home delivery from Gurnee, IL
Price includes $124 shipping
Great Deal
$25,500
- Year:
- 2022
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 310 hp 2.7L I4
- Exterior color:
- Gray
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 83,315
- Stock #:
- C0N103509
- VIN:
- 1GCPYCEK6NZ103509
New arrival
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
83,315 mi
Valparaiso, IN
16 mi away
Fair Deal
$29,221
- 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:
- Black
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Mileage:
- 11,800
- Stock #:
- GP478A
- VIN:
- 3GCUKCED8SG254868
Sponsored Listing
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
11,800 mi
Demotte, IN
28 mi away
Good Deal
$44,867
FAQs
How much does the Chevrolet Silverado 1500 Custom Trail Boss cost in Gary, IN?
The average Chevrolet Silverado 1500 Custom Trail Boss costs about $26,175.04. The average price has decreased by -4.1% since last year. The 179 for sale near Gary, IN on CarGurus, range from $16,279 to $63,008 in price.
How many Chevrolet Silverado 1500 Custom Trail Boss vehicles in Gary, IN have no reported accidents or damage?
165 out of 179 for sale near Gary, IN 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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