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 Stewardson, IL

155 results
Stewardson, IL
2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Leman's Chevy City

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

22,611 miles

$33,495

Great Deal
Bloomington, IL
83 mi away
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:
Glacier Blue Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
22,611
Stock number:
QBP4609A
VIN:
3GCPDCEK8NG686354

Sponsored

2019 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

62,169 miles

$29,495

Fair Deal
Springfield, IL
62 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:
Blue
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
6-Speed Automatic
Mileage:
62,169
Stock number:
40793
VIN:
3GCPYCEF6KG135326

Sponsored

2025 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

15,835 miles

$41,762

Fair Deal
Belleville, IL
91 mi away
Year:
2025
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
310 hp 2.7L I4
Exterior color:
Summit White
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Transmission:
8-Speed Automatic
Mileage:
15,835
Stock number:
A6620
VIN:
3GCPKCEKXSG190280

Sponsored

2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

22,611 miles

$33,495

Great Deal
Bloomington, IL
83 mi away
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:
Glacier Blue Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
22,611
Stock number:
QBP4609A
VIN:
3GCPDCEK8NG686354

2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

50,417 miles

$32,497

Good Deal
Store transfer to Springfield, IL
220 mi away • Price includes $499 shipping Price includes $499 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

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

14,987 miles

$43,495

Great Deal
Certified Pre-Owned
Collinsville, IL
84 mi away
Year:
2025
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
3L I6 Diesel
Exterior color:
Sterling Gray Metallic
Combined gas mileage:
23 MPG
Fuel type:
Diesel
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
14,987
Stock number:
L261985A
VIN:
3GCUKCE83SG133488

Preparing for a close up...

Photos coming soon

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

15,835 miles

$41,762

Fair Deal
Belleville, IL
91 mi away
Year:
2025
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
310 hp 2.7L I4
Exterior color:
Summit White
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Transmission:
8-Speed Automatic
Mileage:
15,835
Stock number:
A6620
VIN:
3GCPKCEKXSG190280

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

32,627 miles

$37,990

Fair Deal
Germantown, IL
71 mi away
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:
Dark Ash Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
32,627
Stock number:
26233B
VIN:
3GCPDCED1NG676170

Preparing for a close up...

Photos coming soon

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

5,739 miles

$45,911

Good Deal
Decatur, IL
45 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:
Black
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
5,739
Stock number:
SG167426
VIN:
3GCUKCED1SG167426

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

81,655 miles

$27,495

Great Deal
Springfield, IL
62 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:
Black
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic
Mileage:
81,655
Stock number:
372067
VIN:
3GCPYCEF5MG372067

Sponsored

  1. Home
  2. / Used Cars
  3. / Chevrolet Silverado 1500
  4. / Custom Trail Boss
  5. / Illinois
  6. / Stewardson
  • Chevrolet Silverado 1500 LT in Stewardson IL

  • Chevrolet Silverado 1500 RST in Stewardson IL

  • Chevrolet Silverado 1500 LTZ in Stewardson IL

  • Chevrolet Silverado 1500 LT Trail Boss in Stewardson IL

  • Chevrolet Silverado 1500 LT1 in Stewardson IL

  • Chevrolet Silverado 1500 Custom in Stewardson IL

  • Chevrolet Silverado 1500 High Country in Stewardson IL

  • Chevrolet Silverado 1500 Custom Trail Boss in Stewardson IL

  • Chevrolet Silverado 1500 Work Truck in Stewardson IL

  • Chevrolet Silverado 1500 in Decatur IL

  • Chevrolet Silverado 1500 in Champaign IL

  • Chevrolet Silverado 1500 in Terre Haute IN

  • Chevrolet Silverado 1500 in Springfield IL

  • Chevrolet Silverado 1500 in Bloomington IL

  • Chevrolet Silverado 1500 in Saint Louis MO

  • Chevrolet Silverado 1500 in Evansville IN

  • Chevrolet Silverado 1500 in Crawfordsville IN

  • Chevrolet Silverado 1500 in Jasper IN

  • Chevrolet Silverado 1500 in Stewardson IL

  • Old Chevy Trucks for Sale in Stewardson IL

  • Classic Muscle Cars for Sale in Stewardson IL

  • Chevrolet Trucks For Sale in Stewardson IL

  • Cheap Muscle Cars for Sale in Stewardson IL

  • Work Trucks for Sale in Stewardson IL

  • Reliable Cars For Sale in Stewardson IL

  • American Made Trucks For Sale in Stewardson IL

  • Best Pickup Trucks For Sale in Stewardson IL

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

  • 2019 Chevrolet Silverado 1500 Custom Trail Boss in Stewardson 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

  • Leach Wilson Chevrolet Co.

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.