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 Bridgeview, IL

161 results
Bridgeview, IL
2023 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Ray Chevrolet

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

67,555 miles

$34,998

Fair Deal
Certified Pre-Owned
Fox Lake, IL
50 mi away
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:
Dark Ash Metallic
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
67,555
Stock number:
49474A
VIN:
3GCPDCEK6PG167810

Sponsored

2023 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

45,678 miles

$38,877

Fair Deal
Elmhurst, IL
15 mi away
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:
Summit White
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
45,678
Stock number:
P6036
VIN:
3GCUDCED1PG323353

Sponsored

2019 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

101,130 miles

$25,777

Good Deal
Morris, IL
41 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:
Summit White
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
101,130
Stock number:
FT11528A
VIN:
1GCPYCEF2KZ233267

Sponsored

2019 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

101,130 miles

$25,777

Good Deal
Morris, IL
41 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:
Summit White
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
101,130
Stock number:
FT11528A
VIN:
1GCPYCEF2KZ233267

2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

65,899 miles

$29,789

Good Deal
Gurnee, IL
46 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Cherry Red Tintcoat
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
65,899
Stock number:
GB31045
VIN:
3GCPYCEK9NG139355

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

24,159 miles

$38,582

Fair Deal
Certified Pre-Owned
Bolingbrook, IL
14 mi away
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:
Glacier Blue Metallic
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
24,159
Stock number:
49138A
VIN:
3GCPDCEK1PG339273

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

118,420 miles

$25,363

Fair Deal
Certified Pre-Owned
Melrose Park, IL
12 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

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

50,417 miles

$32,197

Good Deal
Store transfer to Oak Lawn, IL
241 mi away • Price includes $199 shipping Price includes $199 shipping
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Black
Interior color:
Black
Transmission:
Automatic
Mileage:
50,417
Stock number:
27851520
VIN:
3GCPYCEK9NG185283

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

71,976 miles

$31,794

Fair Deal
Matteson, IL
17 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:
White
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
71,976
Stock number:
WV15855
VIN:
1GCPYCEF4MZ438429

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

98,286 miles

$26,836

Good Deal
Elmhurst, IL
15 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Gray (Satin Steel Metallic)
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
98,286
Stock number:
3632A
VIN:
3GCPYCEK2NG153209

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

83,392 miles

$31,499

Fair Deal
Certified Pre-Owned
Fox Lake, IL
50 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:
83,392
Stock number:
48945A
VIN:
1GCPYCEF1MZ215913

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

15,243 miles

$39,900

Fair Deal
Bradley, IL
40 mi away
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:
Red Hot G7c
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Jet Black H0u
Transmission:
8-Speed Automatic
Mileage:
15,243
Stock number:
p3665
VIN:
3GCPDCEKXPG195562

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

31,732 miles

$34,828

Good Deal
Villa Park, IL
13 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
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
31,732
Stock number:
B46674A
VIN:
1GCPYCEF7MZ292172

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

106,129 miles

$25,444

Fair Deal
Huntley, IL
42 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:
Gray (Satin Steel Metallic)
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
106,129
Stock number:
V2765A
VIN:
1GCPYCEF1KZ335255

Sponsored

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

  • Chevrolet Silverado 1500 LT in Bridgeview IL

  • Chevrolet Silverado 1500 RST in Bridgeview IL

  • Chevrolet Silverado 1500 LTZ in Bridgeview IL

  • Chevrolet Silverado 1500 LT Trail Boss in Bridgeview IL

  • Chevrolet Silverado 1500 LT1 in Bridgeview IL

  • Chevrolet Silverado 1500 Custom in Bridgeview IL

  • Chevrolet Silverado 1500 High Country in Bridgeview IL

  • Chevrolet Silverado 1500 Custom Trail Boss in Bridgeview IL

  • Chevrolet Silverado 1500 Work Truck in Bridgeview IL

  • Chevrolet Silverado 1500 in Chicago IL

  • Chevrolet Silverado 1500 in Aurora IL

  • Chevrolet Silverado 1500 in Palatine IL

  • Chevrolet Silverado 1500 in Kenosha WI

  • Chevrolet Silverado 1500 in Rockford IL

  • Chevrolet Silverado 1500 in South Bend IN

  • Chevrolet Silverado 1500 in Milwaukee WI

  • Chevrolet Silverado 1500 in Janesville WI

  • Chevrolet Silverado 1500 in Lafayette IN

  • Chevrolet Silverado 1500 in Bridgeview IL

  • Old Chevy Trucks for Sale in Bridgeview IL

  • Classic Muscle Cars for Sale in Bridgeview IL

  • Chevrolet Trucks For Sale in Bridgeview IL

  • Cheap Muscle Cars for Sale in Bridgeview IL

  • Work Trucks for Sale in Bridgeview IL

  • Reliable Cars For Sale in Bridgeview IL

  • American Made Trucks For Sale in Bridgeview IL

  • Best Pickup Trucks For Sale in Bridgeview IL

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

  • 2019 Chevrolet Silverado 1500 Custom Trail Boss in Bridgeview 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

  • Ray Chevrolet

  • Chevrolet of Merrillville

  • Napleton Chevrolet St. Charles

  • Phillips Chevrolet of Frankfort

  • Martin Chevrolet

  • Chevrolet of Naperville

  • Garber Chevrolet Highland

  • Phillips Chevrolet of Lansing

  • Castle Chevrolet North of Elk Grove Village

  • Route 1 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.