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 Merrillville, IN

142 results
Merrillville, IN
2023 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Garber Chevrolet Highland

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

34,986 miles

$39,762

Fair Deal
Certified Pre-Owned
Highland, IN
9 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
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
34,986
Stock number:
21100975P
VIN:
3GCPDCEK0PG100975

Sponsored

2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

18,119 miles

$42,595

Fair Deal
Des Plaines, IL
49 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

2023 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

36,076 miles

$35,997

Great Deal
Downers Grove, IL
44 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:
Black
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
36,076
Stock number:
P17969
VIN:
3GCPDCEK4PG295785

Sponsored

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

55,336 miles

$32,533

Good Deal
Michigan City, IN
25 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:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
55,336
Stock number:
35-26090A
VIN:
1GCPYCEF4MZ280626

2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

25,925 miles

$37,455

Great Deal
Certified Pre-Owned
Naperville, IL
49 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:
Red Hot
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
25,925
Stock number:
P10383A
VIN:
3GCPDCEK8RG227282

2020 Chevrolet Silverado 1500 Custom Trail Boss Double Cab 4WD

2020 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

96,069 miles

$27,480

Fair Deal
Certified Pre-Owned
Merrillville, IN
2 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:
Black
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
96,069
Stock number:
F3511B
VIN:
1GCRYCEF0LZ184757

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

118,420 miles

$26,295

Fair Deal
Certified Pre-Owned
Melrose Park, IL
41 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

31,732 miles

$35,895

Good Deal
Villa Park, IL
43 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

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

9,788 miles

$44,588

Good Deal
Certified Pre-Owned
Demotte, IN
20 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:
Slate Gray Metallic
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
9,788
Stock number:
G6036A
VIN:
3GCUKCED2SG194361

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

27,989 miles

$38,994

Fair Deal
Certified Pre-Owned
Riverside, IL
36 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:
Black
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
27,989
Stock number:
Z5195
VIN:
3GCPYCEL8NG176342

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

50,704 miles

$33,990

Good Deal
Orland Park, IL
29 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

Sponsored

  1. Home
  2. / Used Cars
  3. / Chevrolet Silverado 1500
  4. / Custom Trail Boss
  5. / Indiana
  6. / Merrillville
  • Chevrolet Silverado 1500 LT in Merrillville IN

  • Chevrolet Silverado 1500 RST in Merrillville IN

  • Chevrolet Silverado 1500 LTZ in Merrillville IN

  • Chevrolet Silverado 1500 LT Trail Boss in Merrillville IN

  • Chevrolet Silverado 1500 LT1 in Merrillville IN

  • Chevrolet Silverado 1500 Custom in Merrillville IN

  • Chevrolet Silverado 1500 High Country in Merrillville IN

  • Chevrolet Silverado 1500 Custom Trail Boss in Merrillville IN

  • Chevrolet Silverado 1500 Work Truck in Merrillville IN

  • Chevrolet Silverado 1500 in Chicago IL

  • Chevrolet Silverado 1500 in Aurora IL

  • Chevrolet Silverado 1500 in South Bend IN

  • Chevrolet Silverado 1500 in Palatine IL

  • Chevrolet Silverado 1500 in Lafayette IN

  • Chevrolet Silverado 1500 in Kenosha WI

  • Chevrolet Silverado 1500 in Kokomo IN

  • Chevrolet Silverado 1500 in Crawfordsville IN

  • Chevrolet Silverado 1500 in Kalamazoo MI

  • Chevrolet Silverado 1500 in Merrillville IN

  • Old Chevy Trucks for Sale in Merrillville IN

  • Classic Muscle Cars for Sale in Merrillville IN

  • Chevrolet Trucks For Sale in Merrillville IN

  • Cheap Muscle Cars for Sale in Merrillville IN

  • Work Trucks for Sale in Merrillville IN

  • Reliable Cars For Sale in Merrillville IN

  • American Made Trucks For Sale in Merrillville IN

  • Best Pickup Trucks For Sale in Merrillville IN

  • Best Cars Under $5,000 For Sale in Merrillville IN

  • 2019 Chevrolet Silverado 1500 Custom Trail Boss in Merrillville IN

  • 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 Bolingbrook

  • Advantage Chevrolet Hodgkins

  • Phillips Chevrolet of Frankfort

  • Chevrolet of Merrillville

  • Jennings Chevrolet

  • Chevrolet of Naperville

  • Phillips Chevrolet of Lansing

  • Sunrise Chevrolet

  • Garber Chevrolet Highland

  • Golf Mill Chevrolet

  • Team Chevrolet

  • Jerry Haggerty 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

© 2025 CarGurus, Inc., All Rights Reserved.