CarGurus Logo Homepage Link
  • Buy
    • Used cars
    • New cars
    • Certified pre-owned
    • Start your purchase online
    • Dealerships near me
  • Sell
    • Sell my car
    • Car values
    • Sell my car FAQs
  • Finance
    • Prequalify for financing
    • How does it work?
    • Financing FAQs
  • Research
    • Test drive reviews
    • Price trends
    • Tips & advice
    • Electric cars
    • Compare cars
  • Discover
    The latest way to shop:
    smarter research, better
    listings.
  • Saved cars & searches
  • Sign in / Register
    • My account
    • Saved searches
    • Saved cars
    • Recommended cars
    • Browsing history
    • Financing dashboard
      • United States (EN)
      • Estados Unidos (ES)
      • Canada (EN)
      • Canada (FR)
      • United Kingdom

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

165 results
Wayne, IL
2025 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Rod Baker Ford

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

5,854 miles

$48,297

Fair Deal
Certified Pre-Owned
Plainfield, IL
23 mi away
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:
Summit White
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
5,854
Stock number:
T26231A
VIN:
3GCUKCED4SG215632

Sponsored

2020 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

118,420 miles

$26,232

Fair Deal
Certified Pre-Owned
Melrose Park, IL
20 mi away
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:
Gray (Satin Steel Metallic)
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
118,420
Stock number:
60890A
VIN:
1GCPYCEF4LZ171792

Sponsored

2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

13,478 miles

$45,599

Fair Deal
Certified Pre-Owned
Sandwich, IL
29 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 Hot
Combined gas mileage:
25 MPG
Fuel type:
Diesel
Interior color:
Black
Transmission:
Automatic
Mileage:
13,478
Stock number:
P7424
VIN:
3GCUDCE88RG424900

Sponsored

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

51,071 miles

$30,000

Fair Deal
Mchenry, IL
26 mi away
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:
Cajun Red Tintcoat
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
51,071
Stock number:
UT20663
VIN:
1GCRYCEF4KZ312867

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

64,074 miles

$31,995

Good Deal
St Charles, IL
3 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:
64,074
Stock number:
26188A
VIN:
1GCPYCEF8MZ210773

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

80,760 miles

$29,997

Good Deal
Morris, IL
41 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:
Gray (Satin Steel Metallic)
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
80,760
Stock number:
GN08548A
VIN:
1GCPYCEF6MZ336274

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

85,764 miles

$29,725

Fair Deal
Kenosha, WI
45 mi away
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:
Summit White
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
85,764
Stock number:
K260109A
VIN:
1GCPYCEF1LZ177050

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

61,002 miles

$27,988

Fair Deal
Dekalb, IL
24 mi away
Year:
2019
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:
Northsky Blue Metallic
Fuel type:
Flex Fuel Vehicle
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
61,002
Stock number:
DT26-25A
VIN:
1GCRYCEH2KZ261970

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

118,420 miles

$26,232

Fair Deal
Certified Pre-Owned
Melrose Park, IL
20 mi away
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:
Gray (Satin Steel Metallic)
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
118,420
Stock number:
60890A
VIN:
1GCPYCEF4LZ171792

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

98,227 miles

$28,910

Good Deal
Certified Pre-Owned
Frankfort, IL
37 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:
Gray (Satin Steel Metallic)
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
98,227
Stock number:
60969A
VIN:
1GCPYCEF5MZ291179

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

114,389 miles

$23,997

Good Deal
Arlington Heights, IL
19 mi away
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:
Red Hot
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
114,389
Stock number:
AN3717A
VIN:
1GCPYCEF4KZ218947

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

50,704 miles

$32,999

Good Deal
Orland Park, IL
32 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:
Cherry Red Tintcoat
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
50,704
Stock number:
B10901
VIN:
1GCPYCEF7MZ410785

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

18,119 miles

$42,595

Fair Deal
Des Plaines, IL
20 mi away
Year:
2024
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
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
18,119
Stock number:
JU18278
VIN:
3GCUDCEDXRG349677

Sponsored

  1. Home
  2. / Used Cars
  3. / Chevrolet Silverado 1500
  4. / Custom Trail Boss
  5. / Illinois
  6. / Wayne

  • Chevrolet Silverado 1500 LT in Wayne IL

  • Chevrolet Silverado 1500 RST in Wayne IL

  • Chevrolet Silverado 1500 LTZ in Wayne IL

  • Chevrolet Silverado 1500 LT Trail Boss in Wayne IL

  • Chevrolet Silverado 1500 LT1 in Wayne IL

  • Chevrolet Silverado 1500 Custom in Wayne IL

  • Chevrolet Silverado 1500 High Country in Wayne IL

  • Chevrolet Silverado 1500 Custom Trail Boss in Wayne IL

  • Chevrolet Silverado 1500 Work Truck in Wayne IL

  • Chevrolet Silverado 1500 in Aurora IL

  • Chevrolet Silverado 1500 in Palatine IL

  • Chevrolet Silverado 1500 in Chicago IL

  • Chevrolet Silverado 1500 in Rockford IL

  • Chevrolet Silverado 1500 in Kenosha WI

  • Chevrolet Silverado 1500 in Janesville WI

  • Chevrolet Silverado 1500 in Milwaukee WI

  • Chevrolet Silverado 1500 in Madison WI

  • Chevrolet Silverado 1500 in Clinton IA

  • Chevrolet Silverado 1500 in Wayne IL

  • Old Chevy Trucks for Sale in Wayne IL

  • Classic Muscle Cars for Sale in Wayne IL

  • Chevrolet Trucks For Sale in Wayne IL

  • Cheap Muscle Cars for Sale in Wayne IL

  • Work Trucks for Sale in Wayne IL

  • Reliable Cars For Sale in Wayne IL

  • American Made Trucks For Sale in Wayne IL

  • Best Pickup Trucks For Sale in Wayne IL

  • Best Cars Under $5,000 For Sale in Wayne IL

  • 2019 Chevrolet Silverado 1500 Custom Trail Boss in Wayne IL

  • All Used Cars

  • Manual Transmission Cars

  • Luxury Cars

  • Cars with Red Interior

  • Cheap Manual Cars

  • Hybrid Cars

  • Sports Cars

  • Electric SUVs

  • Cheap Trucks

  • Small Cars

  • Third Row SUVs

  • Three Quarter Ton Trucks

  • Lifted Trucks

  • Manual Transmission Trucks

  • Diesel Trucks

  • Hybrid SUVs

  • Dually Trucks

  • One Ton Trucks

  • Cheap SUVs

  • Lifted Ford Trucks

  • 4x4 Trucks

  • Work Trucks

  • AWD SUVs

  • Ford Trucks

  • Chevrolet Trucks

  • Toyota Trucks

  • Trucks Under $10,000

  • Cars Under $15,000

  • Sports Cars Under $20,000

  • Trucks Under $20,000

  • Used Sedans for Sale with Low Mileage

  • Used SUVs / Crossovers for Sale with Low Mileage

  • Used Hatchbacks for Sale with Low Mileage

  • Used Convertibles for Sale with Low Mileage

  • Used Vans for Sale with Low Mileage

  • Used Minivans for Sale with Low Mileage

  • Used Pickup Trucks for Sale with Low Mileage

  • Used Coupes for Sale with Low Mileage

  • Used Wagons for Sale with Low Mileage

  • Advantage Chevrolet Hodgkins

  • Advantage Chevrolet Bolingbrook

  • Phillips Chevrolet of Frankfort

  • Ray Chevrolet

  • Napleton Chevrolet St. Charles

  • Jennings Chevrolet

  • Raymond Chevrolet

  • Martin Chevrolet

  • Chevrolet of Naperville

  • Phillips Chevrolet of Lansing

  • Castle Chevrolet North of Elk Grove Village

  • Sunrise Chevrolet

Connect with us
Download our app
Download on the App Store Get it on Google Play
  • Company
  • About CarGurus
  • Our team
  • Press
  • Investor relations
  • Price trends
  • Careers
  • Advertise with CarGurus
  • For dealers
  • Dealer signup
  • Dealer resources
  • Terms
  • Terms of use
  • Privacy policy
  • Interest-based ads
  • Security
  • Help
  • Help center
  • Contact us
Click for the BBB Business Review of this Auto Listing Service in Cambridge MA
    • United States (EN)
    • Estados Unidos (ES)
    • Canada (EN)
    • Canada (FR)
    • United Kingdom

© 2026 CarGurus, Inc., All Rights Reserved.