Used Chevrolet Silverado 1500 Custom Trail Boss for Sale near Carol Stream, IL

132 results

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

59,084 miles

$31,544

Year:: 2022
Make:: Chevrolet
Model:: Silverado 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Exterior color:: Summit White
Interior color:: Jet Black
Transmission:: 8-Speed Automatic
Mileage:: 59,084
Stock #:: 49521A
VIN:: 3GCPYCEK2NG125426

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

128,093 miles

$25,377

Year:: 2021
Make:: Chevrolet
Model:: Silverado 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 355 hp 5.3L V8
Exterior color:: Black
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 6-Speed Automatic
Mileage:: 128,093
Stock #:: JYC-287986
VIN:: 1GCPYCEF3MZ287986

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

71,545 miles

$30,495

Year:: 2022
Make:: Chevrolet
Model:: Silverado 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 310 hp 2.7L I4
Exterior color:: Black
Combined gas mileage:: 18 MPG
Fuel type:: Gasoline
Interior color:: Jet Black
Transmission:: 8-Speed Automatic
Mileage:: 71,545
Stock #:: 26300A
VIN:: 3GCPYCEK5NG116803

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

98,286 miles

$27,500

Year:: 2022
Make:: Chevrolet
Model:: Silverado 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Exterior color:: Gray (Steel Metallic)
Interior color:: Jet Black
Transmission:: 8-Speed Automatic
Mileage:: 98,286
Stock #:: 3632A
VIN:: 3GCPYCEK2NG153209

Home delivery

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

34,578 miles

$35,646

Fair Deal

$691/mo est.

Home delivery from Pueblo, CO

Price includes $1,352 shipping

Year:: 2022
Make:: Chevrolet
Model:: Silverado 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Exterior color:: Blue Metallic
Interior color:: Black
Transmission:: Automatic
Mileage:: 34,578
Stock #:: P149631
VIN:: 1GCPYCEK2NZ149631

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

71,545 miles

$30,495

Year:: 2022
Make:: Chevrolet
Model:: Silverado 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 310 hp 2.7L I4
Exterior color:: Black
Combined gas mileage:: 18 MPG
Fuel type:: Gasoline
Interior color:: Jet Black
Transmission:: 8-Speed Automatic
Mileage:: 71,545
Stock #:: 26300A
VIN:: 3GCPYCEK5NG116803

Home delivery

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

6,220 miles

$48,558

Fair Deal

$910/mo est.

Home delivery from Herculaneum, MO

Price includes $560 shipping

Year:: 2025
Make:: Chevrolet
Model:: Silverado 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 355 hp 5.3L V8
Exterior color:: Black
Fuel type:: Gasoline
Interior color:: Jet Black
Transmission:: 10-Speed Automatic
Mileage:: 6,220
Stock #:: T87306
VIN:: 3GCUKCED8SG344103

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

59,084 miles

$31,544

Year:: 2022
Make:: Chevrolet
Model:: Silverado 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Exterior color:: Summit White
Interior color:: Jet Black
Transmission:: 8-Speed Automatic
Mileage:: 59,084
Stock #:: 49521A
VIN:: 3GCPYCEK2NG125426

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

60,399 miles

$32,902

Year:: 2020
Make:: Chevrolet
Model:: Silverado 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 355 hp 5.3L V8
Exterior color:: Black
Combined gas mileage:: 16 MPG
Fuel type:: Gasoline
Interior color:: Jet Black
Transmission:: 6-Speed Automatic Overdrive
Mileage:: 60,399
Stock #:: P14575
VIN:: 1GCPYCEF4LZ137240

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

47,170 miles

$35,453

Year:: 2021
Make:: Chevrolet
Model:: Silverado 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 420 hp 6.2L V8
Exterior color:: Black
Combined gas mileage:: 17 MPG
Fuel type:: Gasoline
Interior color:: Jet Black
Transmission:: Automatic
Mileage:: 47,170
Stock #:: PCP10136
VIN:: 3GCPYCELXMG167138

Preparing for a close up...

Photos coming soon

Home delivery

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

134,753 miles

$20,899

Good Deal

$409/mo est.

Home delivery from Mechanicsburg, PA

Free home delivery

Year:: 2020
Make:: Chevrolet
Model:: Silverado 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 4.3L V6 Flex Fuel Vehicle
Exterior color:: Shadow Gray Metallic
Combined gas mileage:: 16 MPG
Fuel type:: Flex Fuel Vehicle
Interior color:: Jet Black
Transmission:: 6-Speed Automatic Overdrive
Mileage:: 134,753
Stock #:: 278503A
VIN:: 1GCPYCEH0LZ278503

Preparing for a close up...

Photos coming soon

Home delivery

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

13,599 miles

$41,400

Fair Deal

$788/mo est.

Home delivery from Ashland, OH

Price includes $500 shipping

Year:: 2023
Make:: Chevrolet
Model:: Silverado 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 310 hp 2.7L I4
Exterior color:: Black
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Jet Black
Transmission:: 8-Speed Automatic
Mileage:: 13,599
Stock #:: D5861A
VIN:: 3GCPDCEK9PG299945

Preparing for a close up...

Photos coming soon

Home delivery

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

52,539 miles

$35,636

Fair Deal

$691/mo est.

Home delivery from Columbia, KY

Price includes $637 shipping

Year:: 2021
Make:: Chevrolet
Model:: Silverado 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 355 hp 5.3L V8
Exterior color:: Black
Combined gas mileage:: 15 MPG
Fuel type:: Gasoline
Interior color:: Jet Black
Transmission:: 6-Speed Automatic Overdrive
Mileage:: 52,539
Stock #:: MZ197398
VIN:: 1GCPYCEF7MZ197398

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

104,536 miles

$27,444

Good Deal

$533/mo est.

Third-party certified

Plainfield, IL

20 mi away

Year:: 2021
Make:: Chevrolet
Model:: Silverado 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 355 hp 5.3L V8
Exterior color:: Summit White
Fuel type:: Gasoline
Interior color:: Jet Black
Transmission:: 6-Speed Automatic
Mileage:: 104,536
Stock #:: T26088A
VIN:: 1GCPYCEF4MZ261705

Preparing for a close up...

Photos coming soon

Home delivery

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

118,274 miles

$29,716

Fair Deal

$576/mo est.

Home delivery from Athens, TN

Price includes $728 shipping

Year:: 2022
Make:: Chevrolet
Model:: Silverado 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 355 hp 5.3L V8
Exterior color:: White
Fuel type:: Gasoline
Mileage:: 118,274
Stock #:: C20947
VIN:: 3GCPDCED4NG520947

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

92,193 miles

$25,499

Year:: 2019
Make:: Chevrolet
Model:: Silverado 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 355 hp 5.3L V8
Exterior color:: Black
Combined gas mileage:: 16 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 6-Speed Automatic Overdrive
Mileage:: 92,193
Stock #:: 184482
VIN:: 1GCRYCEF0KZ184482

Preparing for a close up...

Photos coming soon

Home delivery

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

62,775 miles

$30,189

Great Deal

$591/mo est.

Home delivery from Burton, MI

Price includes $239 shipping

Year:: 2020
Make:: Chevrolet
Model:: Silverado 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 355 hp 5.3L V8
Exterior color:: Black
Combined gas mileage:: 16 MPG
Fuel type:: Gasoline
Transmission:: 6-Speed Automatic Overdrive
Mileage:: 62,775
Stock #:: 5019
VIN:: 1GCPYCEF0LZ168095

Preparing for a close up...

Photos coming soon

Home delivery

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

108,686 miles

$25,358

Good Deal

$496/mo est.

Home delivery from Clio, MI

Price includes $363 shipping

Year:: 2019
Make:: Chevrolet
Model:: Silverado 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 355 hp 5.3L V8
Exterior color:: Black
Combined gas mileage:: 16 MPG
Fuel type:: Gasoline
Interior color:: Jet Black
Transmission:: Automatic
Mileage:: 108,686
Stock #:: 12242
VIN:: 1GCPYCEFXKZ379786

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

41,009 miles

$33,877

Year:: 2022
Make:: Chevrolet
Model:: Silverado 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 310 hp 2.7L I4
Exterior color:: Sand Dune Metallic
Combined gas mileage:: 18 MPG
Fuel type:: Gasoline
Interior color:: Jet Black
Transmission:: 8-Speed Automatic
Mileage:: 41,009
Stock #:: J5166A
VIN:: 3GCPDCEK4NG687632

Preparing for a close up...

Photos coming soon

Home delivery

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

70,478 miles

$36,169

Good Deal

$689/mo est.

Home delivery from Houston, TX

Price includes $1,170 shipping

Year:: 2023
Make:: Chevrolet
Model:: Silverado 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 355 hp 5.3L V8
Exterior color:: Dark Ash Metallic
Combined gas mileage:: 18 MPG
Fuel type:: Gasoline
Interior color:: Gray
Transmission:: Automatic
Mileage:: 70,478
VIN:: 3GCUDCED4PG189356

Preparing for a close up...

Photos coming soon

Home delivery

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

110,602 miles

$26,254

Great Deal

$514/mo est.

Home delivery from Indianapolis, IN

Price includes $260 shipping

Year:: 2020
Make:: Chevrolet
Model:: Silverado 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 355 hp 5.3L V8
Exterior color:: Red
Combined gas mileage:: 16 MPG
Fuel type:: Gasoline
Transmission:: 6-Speed Automatic Overdrive
Mileage:: 110,602
Stock #:: 153281
VIN:: 1GCPYCEFXLZ153281

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

13,478 miles

$44,499

Good Deal

$840/mo est.

Manufacturer certified

Sandwich, IL

32 mi away

Year:: 2024
Make:: Chevrolet
Model:: Silverado 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 3L I6 Diesel
Exterior color:: Red
Combined gas mileage:: 25 MPG
Fuel type:: Diesel
Interior color:: Jet Black
Transmission:: Automatic
Mileage:: 13,478
Stock #:: P7424
VIN:: 3GCUDCE88RG424900

Preparing for a close up...

Photos coming soon

Home delivery

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

86,671 miles

$28,057

Fair Deal

$549/mo est.

Home delivery from Homewood , AL

Price includes $1,058 shipping

Year:: 2019
Make:: Chevrolet
Model:: Silverado 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 355 hp 5.3L V8
Exterior color:: Shadow Gray Metallic
Fuel type:: Gasoline
Interior color:: Jet Black
Transmission:: 6-Speed Automatic
Mileage:: 86,671
Stock #:: BT-185260
VIN:: 3GCPYCEFXKG185260

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

47,170 miles

$35,453

Year:: 2021
Make:: Chevrolet
Model:: Silverado 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 420 hp 6.2L V8
Exterior color:: Black
Combined gas mileage:: 17 MPG
Fuel type:: Gasoline
Interior color:: Jet Black
Transmission:: Automatic
Mileage:: 47,170
Stock #:: PCP10136
VIN:: 3GCPYCELXMG167138

A better way to discover your best deal

Let us help you find a car you’ll love.