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Used Chevrolet Silverado 1500 Custom Trail Boss for sale near Brookfield, IL

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21 matches 30 miles from 60513
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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.

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2025 Chevrolet Silverado 1500 Custom Trail Boss
2025 Chevrolet Silverado 1500 Custom Trail Boss
2025 Chevrolet Silverado 1500 Custom Trail Boss
2025 Chevrolet Silverado 1500 Custom Trail Boss
2025 Chevrolet Silverado 1500 Custom Trail Boss
2025 Chevrolet Silverado 1500 Custom Trail Boss View all 60 photos

Used

2025 Chevrolet Silverado 1500 Custom Trail Boss

12 mi.
$48,980
Est. $919/mo*
Free CARFAX 1-Owner Report
Driven Auto of Oak Forest
(58 reviews)
Oak Forest, IL (16 mi.)
Call Check availability Check availability

Vehicle information

Ext. color: Black
Int. color: Jet Black
Drivetrain: Four-wheel Drive
MPG: 16-17
Fuel type: Gasoline
Transmission: 8-Speed Automatic
Engine: 5.3L 8 CYLINDER
Stock #: 8915
VIN: 3GCUKCED9SG253213

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

Reviews

Driven Auto of Oak Forest review

I just got a 2021 Toyota Sienna from driven auto even

August 12, 2025
By Thien Pham from Blaine, MN

I just got a 2021 Toyota Sienna from driven auto even though I live in Minnesota. Comparing the price it’s about 4-5k less from where I live which was concern me about the quality of the car. Big thank you to Basil for helping me testing out the car and the honest feedback, the car is in excellent condition 10 out of 10. Also to Jim doing a great job answering all my questions financing the car, and have it shipped to me earlier than I expected. I definitely going to get another car from here.

2025 Chevrolet Silverado 1500 Custom Trail Boss review

Love this car.

August 16, 2025
By Kommeng from Abilene, tx
Owns this car

Love this car. I wish there was more to the interior though, as it is pretty plain and nothing extraordinary. If they had the bigger infotainment screen for the front bench seat it would have a gotten that one. This car over all is great bang for the buck.

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2024 Chevrolet Silverado 1500 Custom Trail Boss
2024 Chevrolet Silverado 1500 Custom Trail Boss
2024 Chevrolet Silverado 1500 Custom Trail Boss
2024 Chevrolet Silverado 1500 Custom Trail Boss
2024 Chevrolet Silverado 1500 Custom Trail Boss
2024 Chevrolet Silverado 1500 Custom Trail Boss View all 22 photos

Used

2024 Chevrolet Silverado 1500 Custom Trail Boss

13,571 mi.
$43,735 $655 price drop
Est. $820/mo*
Free CARFAX 1-Owner Report
Phillips Chevrolet of Bradley
Bourbonnais, IL (46 mi.)

Vehicle information

Ext. color: Slate Gray Metallic
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 #: B60192A
VIN: 3GCUDCED5RG330843

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, Tow Hooks
Safety: Automatic Emergency Braking, Backup Camera, Brake Assist, Lane Departure Warning, Rear Cross Traffic Alert, Stability Control
2021 Chevrolet Silverado 1500 Custom Trail Boss
2021 Chevrolet Silverado 1500 Custom Trail Boss
2021 Chevrolet Silverado 1500 Custom Trail Boss
2021 Chevrolet Silverado 1500 Custom Trail Boss
2021 Chevrolet Silverado 1500 Custom Trail Boss
2021 Chevrolet Silverado 1500 Custom Trail Boss View all 32 photos

Used

2021 Chevrolet Silverado 1500 Custom Trail Boss

47,744 mi.
$36,985 $300 price drop
Est. $694/mo*
Free CARFAX Report
Bill Kay Honda
Bourbonnais, IL (46 mi.)

Vehicle information

Ext. color: Black
Int. color: Jet Black
Drivetrain: Four-wheel Drive
MPG: 15-20
Fuel type: Gasoline
Transmission: 6-Speed Automatic
Engine: 5.3L V8 16V GDI OHV
Stock #: P7503A
VIN: 1GCPYCEF2MZ232400

Features

Convenience: Keyless Entry, Remote Start
Entertainment: Apple CarPlay®, Bluetooth®, Premium Sound System, Satellite Radio, USB Port
Exterior: Alloy Wheels, Tow Hitch, Tow Hooks
Safety: Backup Camera, Brake Assist, Stability Control
2023 Chevrolet Silverado 1500 Custom Trail Boss
2023 Chevrolet Silverado 1500 Custom Trail Boss
2023 Chevrolet Silverado 1500 Custom Trail Boss
2023 Chevrolet Silverado 1500 Custom Trail Boss
2023 Chevrolet Silverado 1500 Custom Trail Boss
2023 Chevrolet Silverado 1500 Custom Trail Boss View all 21 photos

Used

2023 Chevrolet Silverado 1500 Custom Trail Boss

23,025 mi.
$42,988
Est. $806/mo*
Free CARFAX 1-Owner Report
Michiana Chrysler Dodge Jeep RAM Fiat
Mishawaka, IN (87 mi.)

Vehicle information

Ext. color: Red
Int. color: Jet Black
Drivetrain: Four-wheel Drive
MPG: 17-18
Fuel type: Gasoline
Transmission: 8-Speed Automatic
Engine: 2.7L I4 16V GDI DOHC Turbo
Stock #: 25297A
VIN: 3GCPDCEK3PG306341

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
2021 Chevrolet Silverado 1500 Custom Trail Boss
2021 Chevrolet Silverado 1500 Custom Trail Boss
2021 Chevrolet Silverado 1500 Custom Trail Boss
2021 Chevrolet Silverado 1500 Custom Trail Boss
2021 Chevrolet Silverado 1500 Custom Trail Boss
2021 Chevrolet Silverado 1500 Custom Trail Boss View all 24 photos

Certified

2021 Chevrolet Silverado 1500 Custom Trail Boss

34,679 mi.
$36,517
Est. $685/mo*
Free CARFAX 1-Owner Report
Gordie Boucher Ford Lincoln of Janesville
Janesville, WI (85 mi.)

Vehicle information

Ext. color: Shadow Gray Metallic
Int. color: Jet Black
Drivetrain: Four-wheel Drive
MPG: 15-20
Fuel type: Gasoline
Transmission: 6-Speed Automatic Electronic with Overdrive
Engine: EcoTec3 4.3L V-6 gasoline direct injection, variable valve contr
Stock #: 25FE1030A
VIN: 1GCPYCEH2MZ373534

Features

Convenience: Keyless Entry, 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, Stability Control
2021 Chevrolet Silverado 1500 Custom Trail Boss
2021 Chevrolet Silverado 1500 Custom Trail Boss
2021 Chevrolet Silverado 1500 Custom Trail Boss
2021 Chevrolet Silverado 1500 Custom Trail Boss
2021 Chevrolet Silverado 1500 Custom Trail Boss
2021 Chevrolet Silverado 1500 Custom Trail Boss View all 36 photos

Used

2021 Chevrolet Silverado 1500 Custom Trail Boss

55,115 mi.
$35,387
Est. $664/mo*
Free CARFAX Report
Hiller Ford
Franklin, WI (77 mi.)

Vehicle information

Ext. color: Gray
Int. color: Jet Black
Drivetrain: Four-wheel Drive
MPG: 13-18
Fuel type: Gasoline
Transmission: Automatic
Engine: EcoTec3 5.3L V-8 gasoline direct injection, variable valve contr
Stock #: V7479
VIN: 3GCPYCEFXMG303472

Features

Convenience: Keyless Entry, 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, Stability Control
2022 Chevrolet Silverado 1500 Custom Trail Boss
2022 Chevrolet Silverado 1500 Custom Trail Boss
2022 Chevrolet Silverado 1500 Custom Trail Boss
2022 Chevrolet Silverado 1500 Custom Trail Boss
2022 Chevrolet Silverado 1500 Custom Trail Boss
2022 Chevrolet Silverado 1500 Custom Trail Boss View all 13 photos

Used

2022 Chevrolet Silverado 1500 Custom Trail Boss

49,320 mi.
$33,910 $2,087 price drop
Est. $636/mo*
Free CARFAX 1-Owner Report
Southlake Kia
Merrillville, IN (39 mi.)

Vehicle information

Ext. color: Dark Ash Metallic
Int. color: Black
Drivetrain: Four-wheel Drive
MPG: 16-18
Fuel type: Gasoline
Transmission: 8-Speed Automatic
Engine: 2.7L I4 16V GDI DOHC Turbo
Stock #: S7205A
VIN: 3GCPDCEK7NG644502

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
2021 Chevrolet Silverado 1500 Custom Trail Boss
2021 Chevrolet Silverado 1500 Custom Trail Boss
2021 Chevrolet Silverado 1500 Custom Trail Boss
2021 Chevrolet Silverado 1500 Custom Trail Boss
2021 Chevrolet Silverado 1500 Custom Trail Boss
2021 Chevrolet Silverado 1500 Custom Trail Boss View all 80 photos

Used

2021 Chevrolet Silverado 1500 Custom Trail Boss

89,762 mi.
$32,590 $400 price drop
Est. $611/mo*
Free CARFAX 1-Owner Report
Shaver Preferred Motors
Merriville, IN (35 mi.)

Vehicle information

Ext. color: Cherry Red Tintcoat
Int. color: Jet Black
Drivetrain: Four-wheel Drive
MPG: 14-18
Fuel type: Gasoline
Transmission: Automatic
Engine: EcoTec3 5.3L V-8 gasoline direct injection, variable valve contr
Stock #: 16400
VIN: 1GCPYCEF5MZ276729

Features

Convenience: Keyless Entry, 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, Stability Control
2021 Chevrolet Silverado 1500 Custom Trail Boss
2021 Chevrolet Silverado 1500 Custom Trail Boss
2021 Chevrolet Silverado 1500 Custom Trail Boss
2021 Chevrolet Silverado 1500 Custom Trail Boss
2021 Chevrolet Silverado 1500 Custom Trail Boss
2021 Chevrolet Silverado 1500 Custom Trail Boss View all 35 photos

Used

2021 Chevrolet Silverado 1500 Custom Trail Boss

26,746 mi.
$39,996
Est. $750/mo*
Free CARFAX Report
Janesville Nissan
Janesville, WI (86 mi.)

Vehicle information

Ext. color: Summit White
Int. color: Jet Black
Drivetrain: Four-wheel Drive
MPG: 13-18
Fuel type: Gasoline
Transmission: Automatic
Engine: EcoTec3 5.3L V-8 gasoline direct injection, variable valve contr
Stock #: P30126A
VIN: 3GCPYCEF8MG434545

Features

Convenience: Keyless Entry, Remote Start
Entertainment: Android Auto®, Apple CarPlay®, Bluetooth®, Premium Sound System, Satellite Radio, USB Port, WiFi Hotspot
Exterior: Alloy Wheels, Tow Hitch, Tow Hooks
Safety: Automatic Emergency Braking, Backup Camera, Brake Assist, Stability Control
2021 Chevrolet Silverado 1500 Custom Trail Boss
2021 Chevrolet Silverado 1500 Custom Trail Boss
2021 Chevrolet Silverado 1500 Custom Trail Boss
2021 Chevrolet Silverado 1500 Custom Trail Boss
2021 Chevrolet Silverado 1500 Custom Trail Boss
2021 Chevrolet Silverado 1500 Custom Trail Boss View all 16 photos

Used

2021 Chevrolet Silverado 1500 Custom Trail Boss

40,201 mi.
$38,949
Est. $730/mo*
Get the AutoCheck Report
Bryden Motors
Beloit, WI (77 mi.)

Vehicle information

Ext. color: Cherry Red Tintcoat
Int. color: Jet Black
Drivetrain: Four-wheel Drive
MPG: 13-18
Fuel type: Gasoline
Transmission: Automatic
Engine: EcoTec3 5.3L V-8 gasoline direct injection, variable valve contr
Stock #: UT34561
VIN: 1GCPYCEFXMZ334561

Features

Convenience: Keyless Entry, 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, Stability Control
2021 Chevrolet Silverado 1500 Custom Trail Boss
2021 Chevrolet Silverado 1500 Custom Trail Boss
2021 Chevrolet Silverado 1500 Custom Trail Boss
2021 Chevrolet Silverado 1500 Custom Trail Boss
2021 Chevrolet Silverado 1500 Custom Trail Boss
2021 Chevrolet Silverado 1500 Custom Trail Boss View all 45 photos

Used

2021 Chevrolet Silverado 1500 Custom Trail Boss

80,760 mi.
$32,900 $433 price drop
Est. $617/mo*
Free CARFAX 1-Owner Report
Greenway Autos
Morris, IL (44 mi.)

Vehicle information

Ext. color: Satin Steel Metallic
Int. color: Jet Black
Drivetrain: Four-wheel Drive
MPG: 13-18
Fuel type: Gasoline
Transmission: Automatic
Engine: EcoTec3 5.3L V-8 gasoline direct injection, variable valve contr
Stock #: GN08548A
VIN: 1GCPYCEF6MZ336274

Features

Convenience: Keyless Entry, 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, 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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Chevrolet Silverado 1500 Custom Trail Boss by city

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Chevrolet Silverado 1500 by trim
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