CarGurus Logo Homepage Link
  • Buy
    • Used cars
    • New cars
    • Certified pre-owned
    • Start your purchase online
    • Dealerships near me
  • Sell
    • Sell my car
    • 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 Springfield, IL

162 results
Springfield, IL
2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Clement Supercenter

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

24,380 miles

$38,500

Fair Deal
Saint Charles, MO
85 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
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Transmission:
6-Speed Automatic Overdrive
Mileage:
24,380
Stock number:
A16111N
VIN:
1GCPYCEF3MZ319917

Sponsored

2019 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

62,169 miles

$31,495

Fair Deal
Springfield, IL
2 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

2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

20,583 miles

$39,996

Good Deal
Pekin, IL
54 mi away
Year:
2024
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
310 hp 2.7L I4
Exterior color:
Sterling Gray Metallic
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
20,583
Stock number:
4407H
VIN:
3GCPDCEK3RG409505

Sponsored

2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

12,290 miles

$41,495

Great Deal
Bloomington, IL
58 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:
Sterling Gray Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
12,290
Stock number:
QBP4964
VIN:
3GCUDCED4RG356222

2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

10,100 miles

$41,990

Great Deal
Bloomington, IL
58 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:
Lakeshore Blue Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
10,100
Stock number:
QBP4828
VIN:
3GCUDCED6RG316692

2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

7,649 miles

$44,490

Great Deal
Wood River, IL
69 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:
White
Combined gas mileage:
25 MPG
Fuel type:
Diesel
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
7,649
Stock number:
P7638
VIN:
3GCUDCE84RG456808

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

25,953 miles

$36,776

Great Deal
Wentzville, MO
94 mi away
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:
Red Hot
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
25,953
Stock number:
12835K
VIN:
1GCPYCEL0MZ395200

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

92,650 miles

$26,000

Great Deal
St Louis, MO
97 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:
Cajun Red Tintcoat
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
92,650
Stock number:
S0823BB
VIN:
1GCPYCEF6LZ238568

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

79,889 miles

$29,222

Great Deal
Highland, IL
73 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:
NORTH SKY BLUE METALLIC
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
JET BLACK
Transmission:
Automatic
Mileage:
79,889
Stock number:
26007A
VIN:
3GCPDCEK4NG685380

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

11,210 miles

$40,200

Great Deal
Breese, IL
82 mi away
Year:
2024
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
310 hp 2.7L I4
Exterior color:
Slate Gray Metallic
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
11,210
Stock number:
25105A
VIN:
3GCPDCEK7RG301730

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

16,289 miles

$36,460

Great Deal
Certified Pre-Owned
Bloomington, IL
58 mi away
Year:
2024
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
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
16,289
Stock number:
910052
VIN:
3GCPDCEK5RG210052

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

66,269 miles

$28,695

Fair Deal
Peoria, IL
68 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
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
66,269
Stock number:
51759A
VIN:
1GCRYCEF4KZ204474

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

20,583 miles

$39,996

Good Deal
Pekin, IL
54 mi away
Year:
2024
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
310 hp 2.7L I4
Exterior color:
Sterling Gray Metallic
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
20,583
Stock number:
4407H
VIN:
3GCPDCEK3RG409505

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

36,338 miles

$37,954

Good Deal
Certified Pre-Owned
Springfield, IL
5 mi away
Year:
2024
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
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
36,338
Stock number:
240738A
VIN:
3GCPDCEK8RG114223

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

36,909 miles

$37,667

Fair Deal
Washington, IL
63 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
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
36,909
Stock number:
2130853
VIN:
1GCPYCEFXMZ430853

Sponsored

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

  • Chevrolet Silverado 1500 LT in Springfield IL

  • Chevrolet Silverado 1500 RST in Springfield IL

  • Chevrolet Silverado 1500 LTZ in Springfield IL

  • Chevrolet Silverado 1500 LT Trail Boss in Springfield IL

  • Chevrolet Silverado 1500 LT1 in Springfield IL

  • Chevrolet Silverado 1500 Custom in Springfield IL

  • Chevrolet Silverado 1500 High Country in Springfield IL

  • Chevrolet Silverado 1500 Custom Trail Boss in Springfield IL

  • Chevrolet Silverado 1500 Work Truck in Springfield IL

  • Chevrolet Silverado 1500 in Decatur IL

  • Chevrolet Silverado 1500 in Bloomington IL

  • Chevrolet Silverado 1500 in Peoria IL

  • Chevrolet Silverado 1500 in Champaign IL

  • Chevrolet Silverado 1500 in Saint Louis MO

  • Chevrolet Silverado 1500 in Quincy IL

  • Chevrolet Silverado 1500 in Terre Haute IN

  • Chevrolet Silverado 1500 in Davenport IA

  • Chevrolet Silverado 1500 in Clinton IA

  • Chevrolet Silverado 1500 in Springfield IL

  • Old Chevy Trucks for Sale in Springfield IL

  • Classic Muscle Cars for Sale in Springfield IL

  • Chevrolet Trucks For Sale in Springfield IL

  • Cheap Muscle Cars for Sale in Springfield IL

  • Work Trucks for Sale in Springfield IL

  • Reliable Cars For Sale in Springfield IL

  • American Made Trucks For Sale in Springfield IL

  • Best Pickup Trucks For Sale in Springfield IL

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

  • 2019 Chevrolet Silverado 1500 Custom Trail Boss in Springfield 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

  • Jennings Beardstown, Inc.

  • Friendly Chevrolet

  • Smoky Jennings Chevrolet

  • Victory Lane Motors

  • Baum Chevrolet Buick

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

© 2025 CarGurus, Inc., All Rights Reserved.