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Used
Chevrolet Silverado 1500 Custom Trail Boss
for sale
near
Winnetka, IL
23 matches
30 miles from 60093
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.
Chevrolet Certified
2024 Chevrolet Silverado 1500 Custom Trail Boss
96 mi.
$47,495
$100 price drop
Jerry Haggerty 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: TurboMax 2.7L I-4 gasoline direct injection, DOHC, variable valv
Stock #: C30939
VIN: 3GCPDCEK8RG100113
Features
Convenience:
Keyless Entry, Keyless Start, Remote Start
Entertainment:
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, Rear Cross Traffic Alert, Stability Control
Reviews
Jerry Haggerty Chevrolet review
I absolutely loved Mr.
I absolutely loved Mr. Mike Haggerty's cheerful attitude presented during my car shopping experience. He went out of his way to make sure I was totally satisfied with the purchase, and he made sure the applications needed were downloaded before I left the lot. I can honestly say, of all the years that I've shopped for cars (over 40+ years), this is the first time I've encountered someone who made me feel as if I was a part of his family. His pleasant smile & helpful hospitality will definitely be remembered. Mr. Haggerty's salesmanship was a 10+.
2024 Chevrolet Silverado 1500 Custom Trail Boss review
My 2024 Chevy Silverado LTZ provides a deluxe large SUV
My 2024 Chevy Silverado LTZ provides a deluxe large SUV interior and a standard (short) tuck bed all in one vehicle. It is loaded with features to make it look and operate very well, and it provides mid 20's regular unleaded fuel mileage. The dynamic fuel management system combined with the 10 speed automatic transmission work together flawlessly to deliver smooth power without being able to realize what gear or how many cylinders the powertrain is using at any given time.
Used
2020 Chevrolet Silverado 1500 Custom Trail Boss
38,135 mi.
Not Priced
Midway Autohaus
Vehicle information
Ext. color: WHITE
Int. color: 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 #: 27085
VIN: 1GCPYCEF9LZ325493
Features
Convenience:
Keyless Entry
Entertainment:
Android Auto®, Apple CarPlay®, Bluetooth®, USB Port
Exterior:
Alloy Wheels, Tow Hitch, Tow Hooks
Safety:
Automatic Emergency Braking, Backup Camera, Brake Assist, Stability Control
Reviews
Midway Autohaus review
Great dealer, definitely recommend them, everything went
Great dealer, definitely recommend them, everything went super smooth and I got an amazing rate for financing as well
2020 Chevrolet Silverado 1500 Custom Trail Boss review
Purchased new a 2020 Chevrolet custom Trail Boss in Satin
Purchased new a 2020 Chevrolet custom Trail Boss in Satin Steel metallic, it has been great. I just turned 80,000 miles with no issues, it’s been a pleasure to drive, just replaced brakes and tires for the first time at 75,000 miles . I have also purchased new a 86 F-250 and a 01 GMC 1500 which also were great trucks and sold with 190,000 miles on them. Maintenance is key Chevrolet did a great job on the exterior of this truck, love the look and color. Nothing bad to say only a positive experience.
Used
2019 Chevrolet Silverado 1500 Custom Trail Boss
57,980 mi.
$30,936
Al Piemonte Chevrolet
Vehicle information
Ext. color: Cajun Red Tintcoat
Int. color: Jet Black
Drivetrain: Four-wheel Drive
MPG:
15-20
Fuel type: Gasoline
Transmission: Automatic
Engine: EcoTec3 4.3L V-6 gasoline direct injection, variable valve contr
Stock #: K8529
VIN: 1GCRYCEH2KZ306082
Features
Convenience:
Keyless Entry
Entertainment:
Android Auto®, Apple CarPlay®, Bluetooth®, Premium Sound System, USB Port
Exterior:
Alloy Wheels, Tow Hitch, Tow Hooks
Safety:
Automatic Emergency Braking, Backup Camera, Brake Assist, Lane Departure Warning, Stability Control
Reviews
Al Piemonte Chevrolet review
Kris Kevorkian was such a great sales and got us a great
Kris Kevorkian was such a great sales and got us a great deal on a new car.
2019 Chevrolet Silverado 1500 Custom Trail Boss review
Thumbs up
Since I've owned it, so far so good. I like my truck and I appreciate it everyday. A little bit of shaking in the steering at high speeds but I'm not concerned with it. Overall, pretty great.
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Used
2024 Chevrolet Silverado 1500 Custom Trail Boss
10,570 mi.
$46,387
$101 price drop
Raymond Chevrolet-Kia
Vehicle information
Ext. color: Dark Ash 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 #: 46752A
VIN: 3GCPDCEK4RG421632
Features
Convenience:
Keyless Entry, Keyless Start, Remote Start
Entertainment:
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, Rear Cross Traffic Alert, Stability Control
Used
2022 Chevrolet Silverado 1500 Custom Trail Boss
22,417 mi.
$37,281
$716 price drop
St Charles Chrysler Dodge Jeep RAM
Vehicle information
Ext. color: Summit White
Int. color: Jet Black
Drivetrain: Four-wheel Drive
MPG:
16-18
Fuel type: Gasoline
Transmission: Automatic
Engine: 2.7L I-4 gasoline direct injection, DOHC, variable valve control
Stock #: C9121
VIN: 3GCPDCEK3NG690764
Features
Convenience:
Keyless Entry, Keyless Start, 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, LED Headlights, Lane Departure Warning, Stability Control
Used
2019 Chevrolet Silverado 1500 Custom Trail Boss
68,429 mi.
$28,995
$1,000 price drop
Wilde Toyota
Vehicle information
Ext. color: Black
Int. color: Jet Black
Drivetrain: Four-wheel Drive
MPG:
15-20
Fuel type: Gasoline
Transmission: 6-Speed Automatic Electronic with Overdrive
Engine: EcoTec3 5.3L V8
Stock #: N85746
VIN: 1GCPYCEFXKZ307017
Features
Convenience:
Keyless Entry
Entertainment:
Android Auto®, Apple CarPlay®, Bluetooth®, Premium Sound System, USB Port
Exterior:
Alloy Wheels, Tow Hitch, Tow Hooks
Safety:
Automatic Emergency Braking, Backup Camera, Brake Assist, Stability Control
Used
2023 Chevrolet Silverado 1500 Custom Trail Boss
42,362 mi.
$41,193
$265 price drop
Zeigler GMC of Holland
Vehicle information
Ext. color: Radiant Red Tintcoat
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 #: PG200743
VIN: 3GCUDCED2PG200743
Features
Convenience:
Heated Seats, Heated Steering Wheel, Keyless Entry, Keyless Start, 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
Used
2024 Chevrolet Silverado 1500 Custom Trail Boss
18,453 mi.
$45,977
$500 price drop
Castle Chrysler Dodge Jeep Ram
Vehicle information
Ext. color: Slate Gray Metallic
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 #: E5028A
VIN: 3GCUDCED6RG338868
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, Rear Cross Traffic Alert, Stability Control
Used
2022 Chevrolet Silverado 1500 Custom Trail Boss
75,523 mi.
$34,326
Victory Honda Highland
Vehicle information
Ext. color: Silver Ice Metallic
Int. color: Black
Drivetrain: Four-wheel Drive
MPG:
16-18
Fuel type: Gasoline
Transmission: Automatic
Engine: 2.7L I-4 gasoline direct injection, DOHC, variable valve control
Stock #: 93E05047
VIN: 3GCPDCEK7NG619499
Features
Convenience:
Keyless Entry, Keyless Start, 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
Used
2019 Chevrolet Silverado 1500 Custom Trail Boss
81,971 mi.
$28,000
Chignoli Auto Sales
Vehicle information
Ext. color: Red
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 #: 283240
VIN: 1GCRYCEF6KZ279614
Features
Convenience:
Keyless Entry
Entertainment:
Apple CarPlay®, Bluetooth®, Satellite Radio, USB Port
Exterior:
Alloy Wheels, Tow Hitch, Tow Hooks
Safety:
Backup Camera, Brake Assist, Stability Control
Used
2022 Chevrolet Silverado 1500 Custom Trail Boss
24,440 mi.
$37,995
St Charles Chrysler Dodge Jeep RAM
Vehicle information
Ext. color: Summit White
Drivetrain: Four-wheel Drive
MPG:
16-18
Fuel type: Gasoline
Transmission: Automatic
Engine: 2.7L I-4 gasoline direct injection, DOHC, variable valve control
Stock #: C9226
VIN: 3GCPDCEK0NG686624
Features
Convenience:
Keyless Entry, Keyless Start, 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, Blind Spot Monitor, Brake Assist, LED Headlights, Lane Departure Warning, Stability Control
Used
2023 Chevrolet Silverado 1500 Custom Trail Boss
23,684 mi.
$39,552
$399 price drop
Phillips Chevrolet of Lansing
Vehicle information
Ext. color: Northsky Blue Metallic
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 #: E8425
VIN: 3GCPDCEK4PG188154
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
Used
2020 Chevrolet Silverado 1500 Custom Trail Boss
69,292 mi.
$31,977
$1,000 price drop
Webb Chevy Plainfield
Vehicle information
Ext. color: Red
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 #: 3916P
VIN: 3GCPYCEF3LG285413
Features
Convenience:
Keyless Entry, Remote Start
Entertainment:
Apple CarPlay®, Bluetooth®, USB Port
Exterior:
Alloy Wheels, Tow Hitch, Tow Hooks
Safety:
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.
23 matches
Clear
Chevrolet Silverado 1500 Custom Trail Boss by city
-
Chevrolet Silverado 1500 Custom Trail Boss in Winnetka, IL
1 Great Deal out of 22 listings starting at $28,000
-
Chevrolet Silverado 1500 Custom Trail Boss in Kenilworth, IL
1 Great Deal out of 21 listings starting at $28,000
-
Chevrolet Silverado 1500 Custom Trail Boss in Northfield, IL
1 Great Deal out of 30 listings starting at $25,877
-
Chevrolet Silverado 1500 Custom Trail Boss in Wilmette, IL
1 Great Deal out of 21 listings starting at $28,000
-
Chevrolet Silverado 1500 Custom Trail Boss in Glencoe, IL
1 Great Deal out of 27 listings starting at $25,877
-
Chevrolet Silverado 1500 Custom Trail Boss in Glenview, IL
1 Great Deal out of 30 listings starting at $25,877
-
Chevrolet Silverado 1500 Custom Trail Boss in Evanston, IL
1 Great Deal out of 21 listings starting at $28,000
-
Chevrolet Silverado 1500 Custom Trail Boss in Skokie, IL
1 Great Deal out of 25 listings starting at $28,000
-
Chevrolet Silverado 1500 Custom Trail Boss in Northbrook, IL
1 Great Deal out of 31 listings starting at $25,877
-
Chevrolet Silverado 1500 Custom Trail Boss in Morton Grove, IL
1 Great Deal out of 26 listings starting at $28,000
-
Chevrolet Silverado 1500 Custom Trail Boss in Highland Park, IL
1 Great Deal out of 28 listings starting at $25,877
-
Chevrolet Silverado 1500 Custom Trail Boss in Niles, IL
1 Great Deal out of 26 listings starting at $28,000
Chevrolet Silverado 1500 Custom Trail Boss by year
-
2025 Chevrolet Silverado 1500 Custom Trail Boss
21 listings starting at $46,065
Chevrolet Silverado 1500 by trim
-
Chevrolet Silverado 1500 LT
15 Great Deals out of 64 listings starting at $5,997
-
Chevrolet Silverado 1500 RST
6 Great Deals out of 51 listings starting at $28,595
-
Chevrolet Silverado 1500 LT Trail Boss
3 Great Deals out of 35 listings starting at $24,950
-
Chevrolet Silverado 1500 LTZ
8 Great Deals out of 34 listings starting at $18,995
-
Chevrolet Silverado 1500 Custom
4 Great Deals out of 31 listings starting at $19,595
-
Chevrolet Silverado 1500 1LT
9 Great Deals out of 27 listings starting at $9,999
-
Chevrolet Silverado 1500 2LT
8 Great Deals out of 23 listings starting at $16,995
-
Chevrolet Silverado 1500 Custom Trail Boss
1 Great Deal out of 23 listings starting at $25,877
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This car is likely to sell soon based on the price, features, and condition.
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