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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.
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New and used
2026 Chevrolet Silverado 1500 Custom Trail Boss trucks
for sale
near
Oak Lawn, IL
24 matches
30 miles from 60453
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
$46,249
MSRP $55,795
Mike Anderson Chevrolet of Chicago
Vehicle information
Ext. color: Cypress Gray
Int. color: Jet Black
Drivetrain: Four-wheel Drive
MPG:
17-20
Fuel type: Gasoline
Transmission: 8-Speed Automatic
Engine: TurboMax 2.7L I-4 gasoline direct injection, DOHC, variable valv
Stock #: 000C4498
VIN: 3GCPKCEK1TG136318
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
Mike Anderson Chevrolet of Chicago review
My salesman victor was great.
My salesman victor was great. The process was quick. I did not have to wait hours like at other dealerships I would definitely recommend you check Mike Anderson Chevrolet out. Thanks for everything
New
2026 Chevrolet Silverado 1500 Custom Trail Boss
$53,380
MSRP $56,380
Jennings Chevy / VW
New
2026 Chevrolet Silverado 1500 Custom Trail Boss
$55,274
$250 price drop
Phillips Chevrolet
Vehicle information
Ext. color: Black
Int. color: Black
Drivetrain: Four-wheel Drive
MPG:
16-17
Fuel type: Gasoline
Transmission: 10-Speed Automatic
Engine: 5.3L V8 16V GDI OHV
Stock #: 60235
VIN: 3GCUKCED4TG106685
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
Phillips Chevrolet review
Another great trip to A Phillips Chevy!
Another great trip to A Phillips Chevy!! Fast service, clean shop, friendly service staff. Been buying from Phillips since 2002. Will be back soon, Thank you
New
2026 Chevrolet Silverado 1500 Custom Trail Boss
$53,380
MSRP $56,380
Jennings Chevy / VW
Vehicle information
Ext. color: Sterling Gray Metallic
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 #: T2088
VIN: 3GCPKCEK3TG114661
Features
Convenience:
Keyless Start, Remote Start
Entertainment:
Apple CarPlay®, Bluetooth®, Premium Sound System, Satellite Radio, USB Port, WiFi Hotspot
Exterior:
Alloy Wheels, Tow Hitch, Tow Hooks
Safety:
Backup Camera, Brake Assist, Lane Departure Warning, Stability Control
Reviews
Jennings Chevy / VW review
Loved working with Debbie!
Loved working with Debbie! She was great and made sure I knew everything i needed to about the car and didn't let me worry about a thing!
New
2026 Chevrolet Silverado 1500 Custom Trail Boss
$54,228
Phillips Chevrolet of Lansing
Vehicle information
Ext. color: Red
Int. color: Black
Drivetrain: Four-wheel Drive
MPG:
16-17
Fuel type: Gasoline
Transmission: 10-Speed Automatic
Engine: 5.3L V8 16V GDI OHV
Stock #: L60403
VIN: 3GCUKCED3TG121548
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
Phillips Chevrolet of Lansing review
I just had another great experience with Phillips Chevy.
I just had another great experience with Phillips Chevy. I have worked with Shawn Breish in the past, so I sought him out again to help me find the car I needed. As before, he listened to understand my family's needs, and we discussed costs and options. He was patient with us. We looked at vehicles, test-drove them, and then left to do our own research. That's right, we left with no hard push from their staff to seal the deal quickly. When we returned, Shawn worked with us to negotiate pricing, and we bought the car that we wanted and needed. The Finance rep, Michael, was efficient and answered related questions. This, in addition to the Service Dept, is why Phillips is usually our first and last stop.
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
$54,031
$2,379 price drop
Graff Chevrolet of Chesterton
Vehicle information
Ext. color: Summit White
Int. color: Jet Black
Drivetrain: Four-wheel Drive
MPG:
17-17
Fuel type: Gasoline
Transmission: Automatic
Engine: TurboMax 2.7L I-4 gasoline direct injection, DOHC, variable valv
Stock #: 31-26083
VIN: 3GCPKCEK8TG151236
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
$54,599
Graff Chevrolet GMC of Michigan City
Vehicle information
Ext. color: Black
Int. color: Jet Black
Drivetrain: Four-wheel Drive
MPG:
17-17
Fuel type: Gasoline
Transmission: Automatic
Engine: TurboMax 2.7L I-4 gasoline direct injection, DOHC, variable valv
Stock #: 35-26095
VIN: 3GCPKCEK0TG146600
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
$54,599
Graff Chevrolet GMC of Michigan City
Vehicle information
Ext. color: Sterling Gray Metallic
Int. color: Jet Black
Drivetrain: Four-wheel Drive
MPG:
17-17
Fuel type: Gasoline
Transmission: Automatic
Engine: TurboMax 2.7L I-4 gasoline direct injection, DOHC, variable valv
Stock #: 35-26097
VIN: 3GCPKCEK7TG146593
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
$55,975
Country Chevrolet
Vehicle information
Ext. color: Cypress Gray
Int. color: Jet Black
Drivetrain: Four-wheel Drive
Fuel type: Gasoline
Transmission: Automatic
Engine: TurboMax 2.7L I-4 gasoline direct injection, DOHC, variable valv
Stock #: 1OD14542970
VIN: 3GCPKCEK2TG139471
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
$59,585
MSRP $59,585
LeValley Chevrolet GMC
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 #: CT60078
VIN: 3GCUKCEDXTG146835
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
$59,020
MSRP $59,020
LeValley Chevrolet GMC
Vehicle information
Ext. color: White Sands
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 #: CT60079
VIN: 3GCUKCED6TG146895
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
$47,865
Lynch Chevrolet of Kenosha
Vehicle information
Ext. color: Cypress Gray
Int. color: Jet Black
Drivetrain: Four-wheel Drive
MPG:
17-20
Fuel type: Gasoline
Transmission: 8-speed automatic
Engine: TurboMax 2.7L I-4 gasoline direct injection, DOHC, variable valv
Stock #: K260097
VIN: 3GCPKCEK6TG102391
Features
Convenience:
Keyless Entry, Keyless Start, Navigation System, Remote Start
Entertainment:
Android Auto®, Apple CarPlay®, Bluetooth®, 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
$53,569
Wiers Chevrolet - GMC
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 #: G6018
VIN: 3GCUKCEDXTG145636
Features
Convenience:
Keyless Entry, Keyless Start, Navigation System, Remote Start
Entertainment:
Android Auto®, Apple CarPlay®, Bluetooth®, 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
$57,870
MSRP $60,870
Dominion 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 #: 4355
VIN: 3GCUKCED4TG134258
Features
Convenience:
Keyless Entry, Keyless Start, Navigation System, Remote Start
Entertainment:
Android Auto®, Apple CarPlay®, Bluetooth®, 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
$54,557
Kunes Chevrolet GMC of Elkhorn
Vehicle information
Ext. color: Summit White
Int. color: Black
Drivetrain: Four-wheel Drive
MPG:
17-25
Fuel type: Diesel
Transmission: Automatic
Engine: Duramax 3L I-6 diesel direct injection, DOHC, variable valve con
Stock #: 06T3774
VIN: 3GCUKCE83TG119236
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
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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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