Used Chevrolet Silverado 1500 Custom Trail Boss for Sale nearPittsfield, IL
162 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- 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:
- Black
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 24,733
- Stock #:
- 52418A
- VIN:
- 3GCUDCED2RG191738
Sponsored by Shottenkirk Chevrolet Buick GMC
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
24,733 mi
Fort Madison, IA
80 mi away
Good Deal
$42,176
- 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:
- Gray
- Transmission:
- 6-Speed Automatic
- Mileage:
- 100,334
- Stock #:
- 42380
- VIN:
- 1GCPYCEF8MZ317516
Sponsored Listing
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
100,334 mi
Springfield, IL
63 mi away
Fair Deal
$29,873
- 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:
- 18,143
- Stock #:
- 4665H
- VIN:
- 3GCPDCEK7RG333268
Sponsored Listing
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
18,143 mi
Pekin, IL
91 mi away
Fair Deal
$42,996
- 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:
- Black
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 24,733
- Stock #:
- 52418A
- VIN:
- 3GCUDCED2RG191738
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
24,733 mi
Fort Madison, IA
80 mi away
Good Deal
$42,176
- 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:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 55,063
- Stock #:
- Y7269
- VIN:
- 1GCPYCEF3KZ428293
Price drop
-$881
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
55,063 mi
Fort Madison, IA
80 mi away
Fair Deal
$32,009
$31,128
- 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:
- Northsky Blue Metallic
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black, Cloth Seat Trim
- Transmission:
- Automatic
- Mileage:
- 63,170
- Stock #:
- 43884-1
- VIN:
- 1GCPYCEF1KZ246771
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
63,170 mi
O'Fallon, IL
81 mi away
Good Deal
$31,587
- 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:
- Black
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 43,406
- Stock #:
- J4113A
- VIN:
- 3GCPDCEK9PG115541
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
43,406 mi
Germantown, IL
95 mi away
Fair Deal
$38,104
- 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:
- Black
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 51,065
- Stock #:
- 22696A
- VIN:
- 3GCPDCEK3PG106074
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
51,065 mi
Home delivery from Tampa, FL
Price includes $974 shipping
Great Deal
$35,953
- 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:
- 82,669
- Stock #:
- L265819A
- VIN:
- 3GCPDCED9NG674473
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
82,669 mi
Collinsville, IL
73 mi away
Fair Deal
$34,372
- 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:
- 34,064
- Stock #:
- 4672H
- VIN:
- 3GCUDCED0PG337650
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
34,064 mi
Pekin, IL
91 mi away
Fair Deal
$42,996
- 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:
- Summit White
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 8,465
- Stock #:
- K63288A
- VIN:
- 1GCPYCEL7NZ224929
Price drop
-$2,000
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
8,465 mi
Home delivery from Waukee, IA
Price includes $321 shipping
Good Deal
$41,500
$39,500
- 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:
- Summit White
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 104,500
- Stock #:
- 184422C01
- VIN:
- 1GCPYCEF3LZ184422
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
104,500 mi
Home delivery from Linden , NJ
Price includes $1,312 shipping
Great Deal
$26,112
- 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:
- Summit White
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 53,768
- Stock #:
- PM174391
- VIN:
- 1GCPYCEL0NZ174391
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
53,768 mi
Home delivery from Pleasantville, NJ
Price includes $1,634 shipping
Good Deal
$37,079
- Year:
- 2026
- 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:
- 22 MPG
- Fuel type:
- Diesel
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 13,706
- Stock #:
- TG302482A
- VIN:
- 3GCUKCE8XTG138866
Price drop
-$997
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
13,706 mi
Home delivery from Savannah, MO
Free home delivery
Great Deal
$47,093
$46,096
- 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:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 24,034
- Stock #:
- TRG431087
- VIN:
- 3GCUDCED5RG431087
Price drop
-$1,669
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
24,034 mi
Home delivery from Cleveland, TN
Price includes $1,780 shipping
Great Deal
$43,531
$41,862
- 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:
- Gray
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 62,775
- Stock #:
- 5019
- VIN:
- 1GCPYCEF0LZ168095
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
62,775 mi
Home delivery from Burton, MI
Price includes $437 shipping
Great Deal
$29,437
- 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:
- Jet Black Cloth
- Transmission:
- Automatic
- Mileage:
- 80,250
- Stock #:
- T260680A
- VIN:
- 3GCPDCED6NG587632
New arrival
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
80,250 mi
Hazelwood, MO
59 mi away
Fair Deal
$35,219
- 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:
- Summit White
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 59,609
- Stock #:
- W167457
- VIN:
- 1GCPYCEF3LZ167457
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
59,609 mi
Home delivery from West Valley City, UT
Price includes $1,118 shipping
Good Deal
$32,745
- 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
- Combined gas mileage:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 92,062
- Stock #:
- CMZ379119
- VIN:
- 1GCPYCEF0MZ379119
New arrival
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
92,062 mi
Chesterfield, MO
63 mi away
Good Deal
$29,608
- 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:
- 49,453
- Stock #:
- ZC26344
- VIN:
- 1GCPYCEK2NZ120128
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
49,453 mi
Home delivery from Hicksville, OH
Price includes $424 shipping
Great Deal
$32,659
- 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
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 116,663
- Stock #:
- KZ198554
- VIN:
- 1GCPYCEF4KZ198554
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
116,663 mi
Hillsboro, MO
95 mi away
Good Deal
$24,991
- 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
- Transmission:
- Automatic
- Mileage:
- 89,467
- Stock #:
- P581637B
- VIN:
- 3GCPDCED8NG581637
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
89,467 mi
Home delivery from Livingston, TX
Price includes $981 shipping
Fair Deal
$33,761
- 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:
- Glacier Blue Metallic
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 82,773
- Stock #:
- 54173
- VIN:
- 3GCPDCEK6NG533147
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
82,773 mi
Home delivery from Cambridge, OH
Price includes $366 shipping
Fair Deal
$31,643
- 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:
- 12,437
- Stock #:
- 4593H
- VIN:
- 3GCPDCEK9RG100010
Sponsored Listing
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
12,437 mi
Pekin, IL
91 mi away
Fair Deal
$42,996
FAQs
How much does the Chevrolet Silverado 1500 Custom Trail Boss cost in Pittsfield, IL?
The average Chevrolet Silverado 1500 Custom Trail Boss costs about $27,074.75. The average price has decreased by -0.6% since last year. The 133 for sale near Pittsfield, IL on CarGurus, range from $22,561 to $63,236 in price.
How many Chevrolet Silverado 1500 Custom Trail Boss vehicles in Pittsfield, IL have no reported accidents or damage?
114 out of 133 for sale near Pittsfield, 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.
Relevant articles
Craig Fitzgerald
The Best Cars to Tow Behind an RV in 2026
Not many new models can be towed behind an RV. We’ve identified several that are recommended for flat-towing according to their owner’s manual, and a few used models that have fewer technological or engineering restrictions.
CarGurus Editorial Team
Car Deals with 0% APR in July 2026
Our experts have tracked down the latest 0% APR car deals, as well as examined the pros and cons of interest-free car loans versus other financing options.
CarGurus Editorial Team
Best Truck Lease Deals in July 2026
Leasing a truck can be a great way to get into one of the latest models, with the best technology, at a more affordable monthly price. Here are the best deals we've found this month.
Chevrolet Silverado 1500 LT in Pittsfield ILChevrolet Silverado 1500 RST in Pittsfield ILChevrolet Silverado 1500 LTZ in Pittsfield ILChevrolet Silverado 1500 LT Trail Boss in Pittsfield ILChevrolet Silverado 1500 LT1 in Pittsfield ILChevrolet Silverado 1500 High Country in Pittsfield ILChevrolet Silverado 1500 Custom in Pittsfield ILChevrolet Silverado 1500 Custom Trail Boss in Pittsfield ILChevrolet Silverado 1500 Work Truck in Pittsfield IL
Chevrolet Silverado 1500 in Quincy ILChevrolet Silverado 1500 in Springfield ILChevrolet Silverado 1500 in Saint Louis MOChevrolet Silverado 1500 in Columbia MOChevrolet Silverado 1500 in Peoria ILChevrolet Silverado 1500 in Decatur ILChevrolet Silverado 1500 in Jefferson City MOChevrolet Silverado 1500 in Bloomington ILChevrolet Silverado 1500 in Rolla MO
Chevrolet Silverado 1500 in Pittsfield ILOld Chevy Trucks for Sale in Pittsfield ILClassic Muscle Cars for Sale in Pittsfield ILChevrolet Trucks For Sale in Pittsfield ILCheap Muscle Cars for Sale in Pittsfield ILWork Trucks for Sale in Pittsfield ILReliable Cars For Sale in Pittsfield ILAmerican Made Trucks For Sale in Pittsfield ILBest Pickup Trucks For Sale in Pittsfield ILBest Cars Under $5,000 For Sale in Pittsfield IL
All Used CarsManual Transmission CarsLuxury CarsCars with Red InteriorCheap Manual CarsHybrid CarsSports CarsElectric SUVsCheap TrucksSmall CarsThird Row SUVsThree Quarter Ton TrucksLifted TrucksManual Transmission TrucksDiesel TrucksHybrid SUVsDually TrucksOne Ton TrucksCheap SUVsLifted Ford Trucks4x4 TrucksWork TrucksAWD SUVsFord TrucksChevrolet TrucksToyota TrucksTrucks Under $10,000Cars Under $15,000Sports Cars Under $20,000Trucks Under $20,000Used Sedans for Sale with Low Mileage in PittsfieldUsed SUVs / Crossovers for Sale with Low Mileage in PittsfieldUsed Hatchbacks for Sale with Low Mileage in PittsfieldUsed Convertibles for Sale with Low Mileage in PittsfieldUsed Vans for Sale with Low Mileage in PittsfieldUsed Minivans for Sale with Low Mileage in PittsfieldUsed Pickup Trucks for Sale with Low Mileage in PittsfieldUsed Coupes for Sale with Low Mileage in PittsfieldUsed Wagons for Sale with Low Mileage in Pittsfield
