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 LT Trail Boss for Sale near Kenosha, WI

300 results
Kenosha, WI
2024 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD Elgin Volkswagen

2024 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

65,509 miles

$39,991

Good Deal
Elgin, IL
45 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:
Jet Black
Transmission:
Automatic
Mileage:
65,509
Stock number:
P2893
VIN:
3GCUDFED5RG159187

Sponsored

2020 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

106,186 miles

$31,996

Fair Deal
Marengo, IL
47 mi away
Year:
2020
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
420 hp 6.2L V8
Exterior color:
Gray
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
106,186
Stock number:
6965B
VIN:
1GCPYFEL3LZ256534

Sponsored

2021 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

54,493 miles

$37,598

Good Deal
Certified Pre-Owned
Milwaukee, WI
27 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:
Summit White
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
54,493
Stock number:
C19521N
VIN:
1GCPYFEL8MZ366769

Sponsored

2024 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2024 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

65,509 miles

$39,991

Good Deal
Elgin, IL
45 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:
Jet Black
Transmission:
Automatic
Mileage:
65,509
Stock number:
P2893
VIN:
3GCUDFED5RG159187

2020 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

47,361 miles

$37,977

Fair Deal
Certified Pre-Owned
Milwaukee, WI
27 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:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
47,361
Stock number:
C19605NC
VIN:
1GCPYFED0LZ297695

2021 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

43,657 miles

$39,992

Fair Deal
Kenosha, WI
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:
Black
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
43,657
Stock number:
P13827
VIN:
1GCPYFED4MZ111142

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

68,041 miles

$37,399

Fair Deal
Certified Pre-Owned
Fox Lake, IL
22 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:
Summit White
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
68,041
Stock number:
49292A
VIN:
1GCPYFEL4MZ261551

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

73,662 miles

$34,412

Good Deal
West Allis, WI
31 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:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
73,662
Stock number:
PM4258
VIN:
1GCPYFED0MZ205115

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

104,961 miles

$29,999

Good Deal
Gurnee, IL
16 mi away
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:
104,961
Stock number:
GV1192S
VIN:
3GCPYFELXNG105452

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

15,485 miles

$51,995

Fair Deal
Certified Pre-Owned
Waukesha, WI
36 mi away
Year:
2023
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
420 hp 6.2L V8
Exterior color:
Radiant Red Tintcoat
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
15,485
Stock number:
PB16969
VIN:
3GCUDFEL2PG320907

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

37,770 miles

$40,495

Fair Deal
Hoffman Estates, IL
40 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Summit White
Interior color:
Black
Transmission:
Automatic
Mileage:
37,770
Stock number:
P12201
VIN:
3GCPYFED7NG174494

Sponsored

  1. Home
  2. / Used Cars
  3. / Chevrolet Silverado 1500
  4. / LT Trail Boss
  5. / Wisconsin
  6. / Kenosha
  • Chevrolet Silverado 1500 LT in Kenosha WI

  • Chevrolet Silverado 1500 RST in Kenosha WI

  • Chevrolet Silverado 1500 LTZ in Kenosha WI

  • Chevrolet Silverado 1500 LT Trail Boss in Kenosha WI

  • Chevrolet Silverado 1500 LT1 in Kenosha WI

  • Chevrolet Silverado 1500 Custom in Kenosha WI

  • Chevrolet Silverado 1500 High Country in Kenosha WI

  • Chevrolet Silverado 1500 Custom Trail Boss in Kenosha WI

  • Chevrolet Silverado 1500 Work Truck in Kenosha WI

  • Chevrolet Silverado 1500 in Milwaukee WI

  • Chevrolet Silverado 1500 in Palatine IL

  • Chevrolet Silverado 1500 in Chicago IL

  • Chevrolet Silverado 1500 in Janesville WI

  • Chevrolet Silverado 1500 in Aurora IL

  • Chevrolet Silverado 1500 in Rockford IL

  • Chevrolet Silverado 1500 in Madison WI

  • Chevrolet Silverado 1500 in Fond du Lac WI

  • Chevrolet Silverado 1500 in Holland MI

  • Chevrolet Silverado 1500 in Kenosha WI

  • Old Chevy Trucks for Sale in Kenosha WI

  • Classic Muscle Cars for Sale in Kenosha WI

  • Chevrolet Trucks For Sale in Kenosha WI

  • Cheap Muscle Cars for Sale in Kenosha WI

  • Work Trucks for Sale in Kenosha WI

  • Reliable Cars For Sale in Kenosha WI

  • American Made Trucks For Sale in Kenosha WI

  • Best Pickup Trucks For Sale in Kenosha WI

  • Best Cars Under $5,000 For Sale in Kenosha WI

  • 2019 Chevrolet Silverado 1500 LT Trail Boss in Kenosha WI

  • 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

  • Ray Chevrolet

  • Jennings Chevrolet

  • Martin Chevrolet

  • Lake Chevrolet

  • Castle Chevrolet North of Elk Grove Village

  • Kunes Hope Chevrolet

  • Sunrise Chevrolet

  • Boucher Volkswagen Marketplace

  • Golf Mill Chevrolet

  • The Chevrolet Exchange

  • Napleton Buick GMC Crystal Lake

  • Napleton Palatine 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.