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New and used
2026 Chevrolet Silverado 1500 Custom Trail Boss trucks
for sale
near
Madison, IL
28 matches
30 miles from 62060
Be the first to know!
Est.
$400
/mo*
- Down Payment
- $0
- Net trade-in value
- $0
- Months
- 72
- APR
- 7.0%
- Sales tax
- 0.0%
*Estimated payments are calculated by Cars.com and are for informational purposes only. We’ve estimated your taxes based on your provided ZIP code. These estimates do not include title, registration fees, lien fees, or any other fees that may be imposed by a governmental agency in connection with the sale and financing of the vehicle. Other taxes may apply. They do not represent a financing offer or a guarantee of credit from the seller. Actual terms vary by lender.
**Your Saved Vehicles list will be shared along with your contact information when you submit a vehicle request to a dealership. To opt out of this sharing, please view your options on Cars.com Privacy Notice.
New
2026 Chevrolet Silverado 1500 Custom Trail Boss
$44,910
$1,000 price drop
George Weber Chevrolet Columbia
Vehicle information
Ext. color: White
Int. color: Jet Black
Drivetrain: Four-wheel Drive
MPG:
16-17
Fuel type: Gasoline
Transmission: Automatic
Engine: 2.7L I4 16V GDI DOHC Turbo
Stock #: T260135
VIN: 3GCPKCEK1TG102539
Features
Convenience:
Keyless Entry, Keyless Start, Remote Start
Entertainment:
Android Auto®, Apple CarPlay®, Bluetooth®, Premium Sound System, Satellite Radio, USB Port
Exterior:
Alloy Wheels, Tow Hitch
Safety:
Backup Camera, Brake Assist, Lane Departure Warning, Stability Control
Reviews
George Weber Chevrolet Columbia review
Rich McCabe was extremely professional.
Rich McCabe was extremely professional. He was very knowledgeable and helped me get the best deal for my trade in and my new Colorado. I would recommend Rich to anyone! I will be buying all my cars from Weber Chevrolet moving forward. Thank you Rich!
2026 Chevrolet Silverado 1500 Custom Trail Boss review
This vehicle is 3.
This vehicle is 3.0 Duramax engine. By all means it is a wonderful engine. The internet is reporting problems with it. Although I have not had a problem I am concerned. Super cruise is awesome. GM must resolve any issues because this is by all means the best vehicle on the market right now.
New
2026 Chevrolet Silverado 1500 Custom Trail Boss
$48,392
MSRP $59,445
Jim Butler Chevrolet
Vehicle information
Ext. color: Cypress Gray
Int. color: Jet Black
Drivetrain: Four-wheel Drive
MPG:
15-18
Fuel type: Gasoline
Transmission: 10-Speed Automatic
Engine: EcoTec3 5.3L V-8 gasoline direct injection, variable valve contr
Stock #: 218937
VIN: 3GCUKCED6TG218937
Features
Convenience:
Keyless Entry, Keyless Start, Navigation System, Remote Start
Entertainment:
Android Auto®, Apple CarPlay®, Bluetooth®, Premium Sound System, USB Port, WiFi Hotspot
Exterior:
Alloy Wheels, Tow Hitch, Tow Hooks
Safety:
Automatic Emergency Braking, Backup Camera, Brake Assist, Lane Departure Warning, Stability Control
Reviews
Jim Butler Chevrolet review
Tony, Bryan and Joe made this process painless!
Tony, Bryan and Joe made this process painless! We have bought 3 other vehicles from Jim Butlers in the past 10 years and have never been disappointed
New
2026 Chevrolet Silverado 1500 Custom Trail Boss
$48,488
MSRP $59,550
Jim Butler Chevrolet
Vehicle information
Ext. color: Summit White
Int. color: Jet Black
Drivetrain: Four-wheel Drive
MPG:
15-18
Fuel type: Gasoline
Transmission: 10-Speed Automatic
Engine: EcoTec3 5.3L V-8 gasoline direct injection, variable valve contr
Stock #: 221321
VIN: 3GCUKCED4TG221321
Features
Convenience:
Keyless Entry, Keyless Start, Navigation System, Remote Start
Entertainment:
Android Auto®, Apple CarPlay®, Bluetooth®, Premium Sound System, USB Port, WiFi Hotspot
Exterior:
Alloy Wheels, Tow Hitch, Tow Hooks
Safety:
Automatic Emergency Braking, Backup Camera, Brake Assist, Lane Departure Warning, Stability Control
Reviews
Jim Butler Chevrolet review
I had an excellent experience working with Rodney Brown.
I had an excellent experience working with Rodney Brown. From the very beginning he was knowledgeable, attentive, and genuinely interested in helping me find the right truck. He provided clear, honest recommendations, and I never felt pressured to make a purchase.
New
2026 Chevrolet Silverado 1500 Custom Trail Boss
$51,505
MSRP $55,505
$4,000 price drop
Don Brown Chevrolet
Vehicle information
Ext. color: Red Hot
Int. color: Jet Black
Drivetrain: Four-wheel Drive
MPG:
16-17
Fuel type: Gasoline
Transmission: Automatic
Engine: TurboMax 2.7L I-4 gasoline direct injection, DOHC, variable valv
Stock #: 100797
VIN: 3GCPKCEK8TG119953
Features
Convenience:
Keyless Entry, Keyless Start, Navigation System, Remote Start
Entertainment:
Android Auto®, Apple CarPlay®, Bluetooth®, Premium Sound System, USB Port, WiFi Hotspot
Exterior:
Alloy Wheels, Tow Hitch, Tow Hooks
Safety:
Automatic Emergency Braking, Backup Camera, Brake Assist, Lane Departure Warning, Stability Control
Reviews
Don Brown Chevrolet review
Bought my second vehicle from Don Brown Chevy recently
Bought my second vehicle from Don Brown Chevy recently and when I tell you they treat you like family they really do! They go above and beyond. Making sure you get what you need! Will continue recommending and sending everyone to Don Brown!!
New
2026 Chevrolet Silverado 1500 Custom Trail Boss
$50,446
MSRP $60,870
Jim Butler Chevrolet
Vehicle information
Ext. color: Cypress Gray
Int. color: Jet Black
Drivetrain: Four-wheel Drive
MPG:
21-24
Fuel type: Diesel
Transmission: 10-Speed Automatic
Engine: Duramax 3L I-6 diesel direct injection, DOHC, variable valve con
Stock #: 216538
VIN: 3GCUKCE80TG216538
Features
Convenience:
Keyless Entry, Keyless Start, Navigation System, Remote Start
Entertainment:
Android Auto®, Apple CarPlay®, Bluetooth®, Premium Sound System, USB Port, WiFi Hotspot
Exterior:
Alloy Wheels, Tow Hitch, Tow Hooks
Safety:
Automatic Emergency Braking, Backup Camera, Brake Assist, Lane Departure Warning, Stability Control
Reviews
Jim Butler Chevrolet review
Exceptional experience very good price Brian Ries is a
Exceptional experience very good price Brian Ries is a excellent salesman had vehicle equipped exactly what were looking for
New
2026 Chevrolet Silverado 1500 Custom Trail Boss
$43,190
Weber Chevrolet Creve Coeur
Vehicle information
Ext. color: Sterling Gray Metallic
Int. color: Jet Black
Drivetrain: Four-wheel Drive
MPG:
16-17
Fuel type: Gasoline
Transmission: Automatic
Engine: TurboMax 2.7L I-4 gasoline direct injection, DOHC, variable valv
Stock #: T20432
VIN: 3GCPKCEKXTG208102
Features
Convenience:
Keyless Entry, Keyless Start, Navigation System, Remote Start
Entertainment:
Android Auto®, Apple CarPlay®, Bluetooth®, Premium Sound System, USB Port, WiFi Hotspot
Exterior:
Alloy Wheels, Tow Hitch, Tow Hooks
Safety:
Automatic Emergency Braking, Backup Camera, Brake Assist, Lane Departure Warning, Stability Control
Reviews
Weber Chevrolet Creve Coeur review
Did not care for the finance lady, trying to push the
Did not care for the finance lady, trying to push the extended warranty. It was the exact same sales pitch she tried using on my son back in 2020. It was xx then and was the same now.
New
2026 Chevrolet Silverado 1500 Custom Trail Boss
$49,125
$4,100 price drop
Elco Chevrolet & Cadillac
Vehicle information
Ext. color: Summit White
Int. color: Jet Black
Drivetrain: Four-wheel Drive
MPG:
15-18
Fuel type: Gasoline
Transmission: Automatic
Engine: Gas V8 5.3L/325
Stock #: 2634540
VIN: 3GCUKCED5TG214085
Features
Convenience:
Keyless Entry, Keyless Start, Navigation System, Remote Start
Entertainment:
Bluetooth®, Satellite Radio, WiFi Hotspot
Exterior:
Alloy Wheels, Tow Hitch, Tow Hooks
Safety:
Backup Camera, Lane Departure Warning, Stability Control
Reviews
Elco Chevrolet & Cadillac review
My experience with Hayden was great.
My experience with Hayden was great. He was knowledgeable, courteous, and willing to present my offer on the vehicle. I ended up purchasing in my home state but would highly recommend them based on my experience with them.
New
2026 Chevrolet Silverado 1500 Custom Trail Boss
$44,910
$1,000 price drop
George Weber Chevrolet Columbia
Vehicle information
Ext. color: White
Int. color: Jet Black
Drivetrain: Four-wheel Drive
MPG:
16-17
Fuel type: Gasoline
Transmission: Automatic
Engine: 2.7L I4 16V GDI DOHC Turbo
Stock #: T260271
VIN: 3GCPKCEK6TG127131
Features
Convenience:
Keyless Entry, Keyless Start, Remote Start
Entertainment:
Android Auto®, Apple CarPlay®, Bluetooth®, Premium Sound System, Satellite Radio, USB Port
Exterior:
Alloy Wheels, Tow Hitch
Safety:
Backup Camera, Brake Assist, Lane Departure Warning, Stability Control
Reviews
George Weber Chevrolet Columbia review
Very friendly and courteous staff.
Very friendly and courteous staff. Kurt was great about explaining the features that the truck has to offer.
There are additional matching cars outside your search area.
Partial matches are generated by applying your search criteria to a larger search area. Our goal is to help you discover additional cars that match your search preferences.
As a benefit to some of our dealer customers, we display their listings first.
New
2026 Chevrolet Silverado 1500 Custom Trail Boss
$42,295
Jim Trenary Chevrolet of Troy
Vehicle information
Ext. color: Sterling Gray Metallic
Int. color: Jet Black
Drivetrain: Four-wheel Drive
MPG:
16-21
Fuel type: Gasoline
Transmission: Unknown/ Other
Engine: TurboMax 2.7L I-4 gasoline direct injection, DOHC, variable valv
Stock #: T21270
VIN: 3GCPKCEKXTG198302
Features
Convenience:
Keyless Entry, Keyless Start, Navigation System, Remote Start
Entertainment:
Android Auto®, Apple CarPlay®, Bluetooth®, Satellite Radio, USB Port, WiFi Hotspot
Exterior:
Alloy Wheels, Tow Hitch, Tow Hooks
Safety:
Automatic Emergency Braking, Backup Camera, Brake Assist, Lane Departure Warning, Stability Control
New
2026 Chevrolet Silverado 1500 Custom Trail Boss
$51,426
MSRP $59,154
Sapaugh GM Country
Vehicle information
Ext. color: White Sands
Int. color: Jet Black, Cloth Seat Trim
Drivetrain: Four-wheel Drive
MPG:
15-18
Fuel type: Gasoline
Transmission: Automatic
Engine: EcoTec3 5.3L V-8 gasoline direct injection, variable valve contr
Stock #: 265227
VIN: 3GCUKCED0TG118347
Features
Convenience:
Keyless Entry, Keyless Start, Navigation System, Remote Start
Entertainment:
Android Auto®, Apple CarPlay®, Bluetooth®, Premium Sound System, USB Port, WiFi Hotspot
Exterior:
Alloy Wheels, Tow Hitch, Tow Hooks
Safety:
Automatic Emergency Braking, Backup Camera, Brake Assist, Lane Departure Warning, Stability Control
New
2026 Chevrolet Silverado 1500 Custom Trail Boss
$43,145
Jim Trenary Chevrolet of Troy
Vehicle information
Ext. color: White Sands
Int. color: Jet Black
Drivetrain: Four-wheel Drive
MPG:
16-21
Fuel type: Gasoline
Transmission: Unknown/ Other
Engine: TurboMax 2.7L I-4 gasoline direct injection, DOHC, variable valv
Stock #: T21271
VIN: 3GCPKCEK6TG198149
Features
Convenience:
Keyless Entry, Keyless Start, Navigation System, Remote Start
Entertainment:
Android Auto®, Apple CarPlay®, Bluetooth®, Satellite Radio, USB Port, WiFi Hotspot
Exterior:
Alloy Wheels, Tow Hitch, Tow Hooks
Safety:
Automatic Emergency Braking, Backup Camera, Brake Assist, Lane Departure Warning, Stability Control
New
2026 Chevrolet Silverado 1500 Custom Trail Boss
$49,120
Jim Trenary Chevrolet
Vehicle information
Ext. color: Summit White
Int. color: Jet Black
Drivetrain: Four-wheel Drive
MPG:
16-20
Fuel type: Gasoline
Transmission: Automatic
Engine: TurboMax 2.7L I-4 gasoline direct injection, DOHC, variable valv
Stock #: F261059
VIN: 3GCPKCEK6TG103833
Features
Convenience:
Keyless Entry, Keyless Start, Navigation System, Remote Start
Entertainment:
Android Auto®, Apple CarPlay®, Bluetooth®, Satellite Radio, USB Port, WiFi Hotspot
Exterior:
Alloy Wheels, Tow Hitch, Tow Hooks
Safety:
Automatic Emergency Braking, Backup Camera, Brake Assist, Lane Departure Warning, Stability Control
New
2026 Chevrolet Silverado 1500 Custom Trail Boss
$42,870
Jim Trenary Chevrolet
Vehicle information
Ext. color: Black
Int. color: Jet Black
Drivetrain: Four-wheel Drive
MPG:
17-20
Fuel type: Gasoline
Transmission: Automatic
Engine: TurboMax 2.7L I-4 gasoline direct injection, DOHC, variable valv
Stock #: F260143
VIN: 3GCPKCEK8TG106362
Features
Convenience:
Keyless Entry, Keyless Start, Navigation System, Remote Start
Entertainment:
Android Auto®, Apple CarPlay®, Bluetooth®, Satellite Radio, USB Port, WiFi Hotspot
Exterior:
Alloy Wheels, Tow Hitch, Tow Hooks
Safety:
Automatic Emergency Braking, Backup Camera, Brake Assist, Lane Departure Warning, Stability Control
New
2026 Chevrolet Silverado 1500 Custom Trail Boss
$42,445
Jim Trenary Chevrolet
Vehicle information
Ext. color: Red Hot
Int. color: Jet Black
Drivetrain: Four-wheel Drive
MPG:
17-20
Fuel type: Gasoline
Transmission: Automatic
Engine: TurboMax 2.7L I-4 gasoline direct injection, DOHC, variable valv
Stock #: F260141
VIN: 3GCPKCEK7TG106384
Features
Convenience:
Keyless Entry, Keyless Start, Navigation System, Remote Start
Entertainment:
Android Auto®, Apple CarPlay®, Bluetooth®, Satellite Radio, USB Port, WiFi Hotspot
Exterior:
Alloy Wheels, Tow Hitch, Tow Hooks
Safety:
Automatic Emergency Braking, Backup Camera, Brake Assist, Lane Departure Warning, Stability Control
New
2026 Chevrolet Silverado 1500 Custom Trail Boss
$43,145
Jim Trenary Chevrolet
Vehicle information
Ext. color: Black
Int. color: Jet Black
Drivetrain: Four-wheel Drive
MPG:
17-20
Fuel type: Gasoline
Transmission: Automatic
Engine: TurboMax 2.7L I-4 gasoline direct injection, DOHC, variable valv
Stock #: F261018
VIN: 3GCPKCEK1TG119230
Features
Convenience:
Keyless Entry, Keyless Start, Navigation System, Remote Start
Entertainment:
Android Auto®, Apple CarPlay®, Bluetooth®, Satellite Radio, USB Port, WiFi Hotspot
Exterior:
Alloy Wheels, Tow Hitch, Tow Hooks
Safety:
Automatic Emergency Braking, Backup Camera, Brake Assist, Lane Departure Warning, Stability Control
New
2026 Chevrolet Silverado 1500 Custom Trail Boss
$43,540
Jim Trenary Chevrolet of Troy
Vehicle information
Ext. color: Cypress Gray
Int. color: Jet Black
Drivetrain: Four-wheel Drive
MPG:
16-21
Fuel type: Gasoline
Transmission: Unknown/ Other
Engine: TurboMax 2.7L I-4 gasoline direct injection, DOHC, variable valv
Stock #: T21278
VIN: 3GCPKCEK1TG199757
Features
Convenience:
Keyless Entry, Keyless Start, Navigation System, Remote Start
Entertainment:
Android Auto®, Apple CarPlay®, Bluetooth®, Satellite Radio, USB Port, WiFi Hotspot
Exterior:
Alloy Wheels, Tow Hitch, Tow Hooks
Safety:
Automatic Emergency Braking, Backup Camera, Brake Assist, Lane Departure Warning, Stability Control
No photo available
New
2026 Chevrolet Silverado 1500 Custom Trail Boss
$51,005
$5,000 price drop
Meier Chevrolet
Vehicle information
Ext. color: Cypress
Int. color: Jet Black
Drivetrain: Four-wheel Drive
MPG:
16-17
Fuel type: Gasoline
Transmission: Automatic
Engine: 2.7L I4 16V GDI DOHC Turbo
Stock #: 211237
VIN: 3GCPKCEK4TG211237
Features
Convenience:
Keyless Start, Remote Start
Entertainment:
Apple CarPlay®, Bluetooth®, Premium Sound System, Satellite Radio, USB Port
Exterior:
Alloy Wheels, Tow Hitch
Safety:
Backup Camera, Brake Assist, Lane Departure Warning, Stability Control
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*Estimated payments are calculated by Cars.com and are for informational purposes only. We’ve estimated your taxes based on your provided ZIP code. These estimates do not include title, registration fees, lien fees, or any other fees that may be imposed by a governmental agency in connection with the sale and financing of the vehicle. Other taxes may apply. They do not represent a financing offer or a guarantee of credit from the seller. Actual terms vary by lender.
**Your Saved Vehicles list will be shared along with your contact information when you submit a vehicle request to a dealership. To opt out of this sharing, please view your options on Cars.com Privacy Notice.
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This vehicle is certified pre-owned, backed by a manufacturer warranty, and typically undergoes a rigorous multi-point inspection to ensure quality and reliability.
This vehicle is currently in high demand given its competitive price, desirable features, and overall condition, and may have a higher chance of selling quickly.