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New and used
2025 Chevrolet Silverado 1500 Custom Trail Boss trucks
for sale
near
Des Plaines, IL
25 matches
30 miles from 60019
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
$46,995
$4,000 price drop
The Chevy Exchange
New
2025 Chevrolet Silverado 1500 Custom Trail Boss
$48,766
$3,500 price drop
The Chevy Exchange
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
Thanks Alvin for doing a awesome job with my son on his
Thanks Alvin for doing a awesome job with my son on his first purchase of a car you have great patience and communication 💙💙🫶🏽
New
2025 Chevrolet Silverado 1500 Custom Trail Boss
$47,773
MSRP $55,670
$750 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
$50,255
MSRP $57,505
$1,000 price drop
Currie Motors Chevrolet
Vehicle information
Ext. color: Red Hot
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 #: C8242
VIN: 3GCUKCED6SG281731
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
Couldn’t have asked for a better experience!
Couldn’t have asked for a better experience! Sergio Ramirez, our salesman, was great. Between Sergio and Pete, the financial representative, they spent several hours going over the car functions (we bought an EV) and how EVs drive versus gas cars. Sergio was wonderful, can’t praise him enough. Thank you Currie Motors and Sergio for making our first new car purchase painless and even fun!
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
Our sales consultant was John Lee.
Our sales consultant was John Lee. My husband and I were looking to buy a 2025 Equinox. John was probably the most patient, fair and knowledgeable salesperson I've ever worked with in all the years of us purchasing vehicle. He listened to our requests and concerns and worked with both of us to get the SUV we wanted. Once the deal was finalized, John sat in the SUV with me and went over all the features and buttons to familiarize me. Both my husband and I were very happy with our experience with John and his team members (including Nassar Fakhoury, George Grzywa, and Ed Finn) who helped seal the deal. I highly recommend John and Castle Chevy in Elk Grove Village.
New
2025 Chevrolet Silverado 1500 Custom Trail Boss
$51,461
MSRP $53,605
Libertyville Chevrolet
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 #: T30357
VIN: 3GCPKCEK9SG339827
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
Excellent.
Excellent. Upfront, thorough, and personable. Have checked in after our purchase to ensure satisfaction and answer any questions. Much appreciated!
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
$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
$53,697
Country Chevrolet, Inc. (Herscher)
Vehicle information
Ext. color: Red Hot
Int. color: Jet Black
Drivetrain: Four-wheel Drive
Fuel type: Gasoline
Transmission: TRANSMISSION: 8-SPEED AUTO
Engine: 4 Cylinder
Stock #: 258322
VIN: 3GCPKCEK1SG258322
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
$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
New
2025 Chevrolet Silverado 1500 Custom Trail Boss
$52,490
Bill Walsh Chevrolet of Ottawa
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 #: C15194
VIN: 3GCPKCEK0SG329123
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
$51,990
$3,560 price drop
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 #: C15182
VIN: 3GCPKCEK1SG329227
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
$47,830
Phillips Chevrolet of Bradley
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 #: B50679
VIN: 3GCPKCEK6SG348050
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
$52,990
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 #: C15188
VIN: 3GCPKCEK0SG328666
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
$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
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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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Clear
Chevrolet Silverado 1500 trims
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Chevrolet Silverado 1500 2025 RST
82 listings starting at $49,572
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Chevrolet Silverado 1500 2025 LT
75 listings starting at $40,150
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2 Great Deals out of 62 listings starting at $35,821
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49 listings starting at $32,898
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33 listings starting at $56,486
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25 listings starting at $44,225
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