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New and used
2025 Chevrolet Silverado 1500 Custom Trail Boss trucks
for sale
near
Itasca, IL
27 matches
30 miles from 60143
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
2025 Chevrolet Silverado 1500 Custom Trail Boss
$44,225
MSRP $54,575
$4,000 price drop
Chevrolet of Naperville
Vehicle information
Ext. color: Slate 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 #: T17272
VIN: 3GCPKCEK3SG114335
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
Chevrolet of Naperville review
Had a great experience at Chevrolet of Naperville.
Had a great experience at Chevrolet of Naperville. Everyone was helpful and accommodating, showing me multiple cars and working with me on my trade in value.
2025 Chevrolet Silverado 1500 Custom Trail Boss review
When I first drove this truck I fell in love with it.
When I first drove this truck I fell in love with it. I am recommending this truck to everyone I know. It’s got great power and it is comfortable. It rides surprisingly smooth.
New
2025 Chevrolet Silverado 1500 Custom Trail Boss
$50,532
$1,000 price drop
Webb Chevy Plainfield
New
2025 Chevrolet Silverado 1500 Custom Trail Boss
$47,497
$1,074 price drop
Webb Chevy Plainfield
Vehicle information
Ext. color: Black
Int. color: Jet Black
Drivetrain: Four-wheel Drive
MPG:
16-17
Fuel type: Gasoline
Transmission: 8-Speed Automatic
Engine: 2.7L I4 16V GDI DOHC Turbo
Stock #: 255071
VIN: 3GCPKCEK4SG330324
Features
Convenience:
Keyless Entry, Keyless Start, Remote Start
Entertainment:
Apple CarPlay®, Bluetooth®, Premium Sound System, Satellite Radio, USB Port
Exterior:
Alloy Wheels, Tow Hitch, Tow Hooks
Safety:
Automatic Emergency Braking, Backup Camera, Brake Assist, Lane Departure Warning, Stability Control
Reviews
Webb Chevy Plainfield review
Teaverse
I cried about the price of my tires but to know they are covered was a big load off my shoylders
New
2025 Chevrolet Silverado 1500 Custom Trail Boss
$46,395
MSRP $55,670
$2,128 price drop
Chevrolet of Naperville
Vehicle information
Ext. color: Cypress
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 #: T17933
VIN: 3GCPKCEK7SG347277
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
Chevrolet of Naperville review
Very professional and courteous sales staff.
Very professional and courteous sales staff. Some behind the scenes issues with info I'd received by email being incorrect, but it was solved quick enough.
New
2025 Chevrolet Silverado 1500 Custom Trail Boss
$51,461
MSRP $53,605
Libertyville Chevrolet
Vehicle information
Ext. color: Black
Int. color: Jet Black
Drivetrain: Four-wheel Drive
MPG:
16-17
Fuel type: Gasoline
Transmission: 8-Speed Automatic
Engine: 2.7L I4 16V GDI DOHC Turbo
Stock #: T30356
VIN: 3GCPKCEK2SG338809
Features
Convenience:
Keyless Entry, Keyless Start, Remote Start
Entertainment:
Apple CarPlay®, Bluetooth®, Premium Sound System, Satellite Radio, USB Port
Exterior:
Alloy Wheels, Tow Hitch, Tow Hooks
Safety:
Automatic Emergency Braking, Backup Camera, Brake Assist, Lane Departure Warning, Stability Control
Reviews
Libertyville Chevrolet review
I called in the morning with an alert about the oil level
I called in the morning with an alert about the oil level And without an appointment, I was told I could just come in anytime I was able. The service department was efficient and competent at addressing the issue. Thank you!
New
2025 Chevrolet Silverado 1500 Custom Trail Boss
$46,736
MSRP $54,800
$3,000 price drop
Castle Chevrolet North
Vehicle information
Ext. color: Cypress Gray
Int. color: Jet Black
Drivetrain: Four-wheel Drive
MPG:
16-17
Fuel type: Gasoline
Transmission: 8-Speed Automatic
Engine: TurboMax 2.7L I-4 gasoline direct injection, DOHC, variable valv
Stock #: N24522
VIN: 3GCPKCEK5SG355636
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
Castle Chevrolet North review
Mike G was beyond helpful, From the time we arrived he
Mike G was beyond helpful, From the time we arrived he greeted us and made us feel comfortable. Mike explained everything that would take place and kept us informed through out the day on everything that was being performed on our vehicle.
New
2025 Chevrolet Silverado 1500 Custom Trail Boss
$50,912
$1,000 price drop
Webb Chevy Plainfield
Vehicle information
Ext. color: Cypress
Int. color: Jet Black
Drivetrain: Four-wheel Drive
MPG:
16-17
Fuel type: Gasoline
Transmission: 10-Speed Automatic
Engine: 5.3L V8 16V GDI OHV
Stock #: 255241
VIN: 3GCUKCED3SG339391
Features
Convenience:
Keyless Entry, Keyless Start, Remote Start
Entertainment:
Apple CarPlay®, Bluetooth®, Premium Sound System, Satellite Radio, USB Port
Exterior:
Alloy Wheels, Tow Hitch, Tow Hooks
Safety:
Automatic Emergency Braking, Backup Camera, Brake Assist, Lane Departure Warning, Stability Control
Reviews
Webb Chevy Plainfield review
Great experience
Employees are not pushy, very understandable, fast service. Even had to talk to the parts department and they are the best. Bought our new car and it took less time then we thought. Highly recommend Webb Chevrolet.
New
2025 Chevrolet Silverado 1500 Custom Trail Boss
$50,635
MSRP $58,885
$1,000 price drop
Currie Motors Chevrolet
Vehicle information
Ext. color: Cypress Gray
Int. color: Jet Black
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 #: C8223
VIN: 3GCUKCED8SG321212
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
Currie Motors Chevrolet review
Great customer service.
Great customer service. I have been coming here since 1995 for service. I have bought all my cars from this dealership. The employees are like family.
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
2025 Chevrolet Silverado 1500 Custom Trail Boss
$54,730
Gates Chevy World
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 #: M12616
VIN: 3GCPKCEKXSG323958
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
2025 Chevrolet Silverado 1500 Custom Trail Boss
$52,490
Bill Walsh Chevrolet of Ottawa
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 #: C15176
VIN: 3GCPKCEK3SG311344
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
2025 Chevrolet Silverado 1500 Custom Trail Boss
$54,625
MSRP $56,625
Eric von Schledorn Chevrolet Cadillac
Vehicle information
Ext. color: Black
Int. color: Jet Black
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 #: 24426
VIN: 3GCUKCED6SG304988
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
2025 Chevrolet Silverado 1500 Custom Trail Boss
$52,735
Bill Walsh Chevrolet of Ottawa
Vehicle information
Ext. color: Cypress Gray
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 #: C15164
VIN: 3GCPKCEK6SG310110
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
2025 Chevrolet Silverado 1500 Custom Trail Boss
$54,730
Gates Chevy World
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 #: M12610
VIN: 3GCPKCEK5SG324029
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
2025 Chevrolet Silverado 1500 Custom Trail Boss
$44,245
MSRP $53,365
$7,750 price drop
Mike Anderson Chevrolet Of Merrillville
Vehicle information
Ext. color: Summit White
Int. color: Jet Black
Drivetrain: Four-wheel Drive
MPG:
16-17
Fuel type: Gasoline
Transmission: 8-Speed Automatic
Engine: 2.7L I4 16V GDI DOHC Turbo
Stock #: 00008031
VIN: 3GCPKCEK5SG336892
Features
Convenience:
Keyless Entry, Keyless Start, Remote Start
Entertainment:
Apple CarPlay®, Bluetooth®, Premium Sound System, Satellite Radio, USB Port
Exterior:
Alloy Wheels, Tow Hitch, Tow Hooks
Safety:
Automatic Emergency Braking, Backup Camera, Brake Assist, Lane Departure Warning, Stability Control
New
2025 Chevrolet Silverado 1500 Custom Trail Boss
$53,495
MSRP $56,305
$1,500 price drop
Mike Anderson Chevrolet Of Merrillville
Vehicle information
Ext. color: Red
Int. color: Jet Black
Drivetrain: Four-wheel Drive
MPG:
16-17
Fuel type: Diesel
Transmission: 10-Speed Automatic
Engine: 3.0L I6 24V DDI DOHC Turbo Diesel
Stock #: 00008055
VIN: 3GCUKCE82SG336484
Features
Convenience:
Keyless Entry, Keyless Start, Remote Start
Entertainment:
Apple CarPlay®, Bluetooth®, Premium Sound System, Satellite Radio, USB Port
Exterior:
Alloy Wheels, Tow Hitch, Tow Hooks
Safety:
Automatic Emergency Braking, Backup Camera, Brake Assist, Lane Departure Warning, Stability Control
New
2025 Chevrolet Silverado 1500 Custom Trail Boss
$44,445
MSRP $54,165
$7,750 price drop
Mike Anderson Chevrolet Of Merrillville
Vehicle information
Ext. color: Red
Int. color: Jet Black
Drivetrain: Four-wheel Drive
MPG:
16-17
Fuel type: Gasoline
Transmission: 8-Speed Automatic
Engine: 2.7L I4 16V GDI DOHC Turbo
Stock #: 00008033
VIN: 3GCPKCEK5SG337069
Features
Convenience:
Keyless Entry, Keyless Start, Remote Start
Entertainment:
Apple CarPlay®, Bluetooth®, Premium Sound System, Satellite Radio, USB Port
Exterior:
Alloy Wheels, Tow Hitch, Tow Hooks
Safety:
Automatic Emergency Braking, Backup Camera, Brake Assist, Lane Departure Warning, Stability Control
New
2025 Chevrolet Silverado 1500 Custom Trail Boss
$44,245
MSRP $53,560
$7,750 price drop
Mike Anderson Chevrolet Of Merrillville
Vehicle information
Ext. color: Cypress
Int. color: Jet Black
Drivetrain: Four-wheel Drive
MPG:
16-17
Fuel type: Gasoline
Transmission: 8-Speed Automatic
Engine: 2.7L I4 16V GDI DOHC Turbo
Stock #: 00007043
VIN: 3GCPKCEK6SG307661
Features
Convenience:
Keyless Entry, Keyless Start, Remote Start
Entertainment:
Apple CarPlay®, Bluetooth®, Premium Sound System, Satellite Radio, USB Port
Exterior:
Alloy Wheels, Tow Hitch, Tow Hooks
Safety:
Automatic Emergency Braking, Backup Camera, Brake Assist, Lane Departure Warning, Stability Control
New
2025 Chevrolet Silverado 1500 Custom Trail Boss
$44,745
MSRP $54,560
$7,750 price drop
Mike Anderson Chevrolet Of Merrillville
Vehicle information
Ext. color: Cypress
Int. color: Jet Black
Drivetrain: Four-wheel Drive
MPG:
16-17
Fuel type: Gasoline
Transmission: 8-Speed Automatic
Engine: 2.7L I4 16V GDI DOHC Turbo
Stock #: 00008034
VIN: 3GCPKCEK7SG337865
Features
Convenience:
Keyless Entry, Keyless Start, Remote Start
Entertainment:
Apple CarPlay®, Bluetooth®, Premium Sound System, Satellite Radio, USB Port
Exterior:
Alloy Wheels, Tow Hitch, Tow Hooks
Safety:
Automatic Emergency Braking, 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.
27 matches
Clear
Chevrolet Silverado 1500 trims
-
Chevrolet Silverado 1500 2025 RST
78 listings starting at $49,572
-
Chevrolet Silverado 1500 2025 LT
66 listings starting at $40,150
-
Chevrolet Silverado 1500 2025 Custom
2 Great Deals out of 54 listings starting at $35,821
-
Chevrolet Silverado 1500 2025 WT
45 listings starting at $32,898
-
Chevrolet Silverado 1500 2025 LT Trail Boss
32 listings starting at $56,486
-
Chevrolet Silverado 1500 2025 Custom Trail Boss
27 listings starting at $44,225
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