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 Darien, IL

333 results
Darien, IL
2023 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD Advantage Toyota of River Oaks

2023 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

51,141 miles

$41,373

Good Deal
Certified Pre-Owned
Calumet City, IL
24 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:
51,141
Stock number:
P7122
VIN:
3GCUDFED6PG313760

Sponsored

2020 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

59,812 miles

$34,999

Fair Deal
Hoffman Estates, IL
22 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:
Shadow Gray Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
59,812
Stock number:
PM5700AA
VIN:
1GCPYFED3LZ106738

Sponsored

2023 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2023 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

62,894 miles

$39,885

Good Deal
Sycamore, IL
41 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:
62,894
Stock number:
39P1495
VIN:
3GCUDFED3PG338731

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
26 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

2021 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

62,357 miles

$35,972

Good Deal
Bolingbrook, IL
6 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:
62,357
Stock number:
49459B
VIN:
3GCPYFEL8MG454706

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

35,321 miles

$38,495

Good Deal
Certified Pre-Owned
Bridgeview, IL
10 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Northsky Blue Metallic
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
35,321
Stock number:
JP2804
VIN:
1GCPYFEL1NZ156676

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

15,366 miles

$40,636

Good Deal
Merrillville, IN
38 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:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
15,366
Stock number:
P1099
VIN:
3GCPYFEDXMG434773

Preparing for a close up...

Photos coming soon

2025 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

10,730 miles

$53,999

Good Deal
Certified Pre-Owned
Naperville, IL
10 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:
Cypress Gray
Combined gas mileage:
23 MPG
Fuel type:
Diesel
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
10,730
Stock number:
K6987
VIN:
3GCUKFE89SG246184

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
46 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

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

23,579 miles

$46,972

Fair Deal
Certified Pre-Owned
Bolingbrook, IL
6 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:
Northsky Blue Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
23,579
Stock number:
P15836
VIN:
3GCUDFED4NG617117

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

93,820 miles

$30,995

Fair Deal
Bourbonnais, 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
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
93,820
Stock number:
B5355D
VIN:
1GCPYFED1KZ155449

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

72,708 miles

$33,400

Good Deal
Westmont, IL
5 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:
Silver Ice Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
72,708
Stock number:
D3373B
VIN:
1GCPYFED9MZ169568

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

74,707 miles

$32,293

Fair Deal
Saint Charles, IL
20 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:
Black
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
74,707
Stock number:
F4832
VIN:
1GCPYFEDXKZ123602

Sponsored

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

  • Chevrolet Silverado 1500 RST in Darien IL

  • Chevrolet Silverado 1500 LTZ in Darien IL

  • Chevrolet Silverado 1500 LT Trail Boss in Darien IL

  • Chevrolet Silverado 1500 LT1 in Darien IL

  • Chevrolet Silverado 1500 Custom in Darien IL

  • Chevrolet Silverado 1500 High Country in Darien IL

  • Chevrolet Silverado 1500 Custom Trail Boss in Darien IL

  • Chevrolet Silverado 1500 Work Truck in Darien IL

  • Chevrolet Silverado 1500 in Aurora IL

  • Chevrolet Silverado 1500 in Chicago IL

  • Chevrolet Silverado 1500 in Palatine IL

  • Chevrolet Silverado 1500 in Kenosha WI

  • Chevrolet Silverado 1500 in Rockford IL

  • Chevrolet Silverado 1500 in Janesville WI

  • Chevrolet Silverado 1500 in South Bend IN

  • Chevrolet Silverado 1500 in Milwaukee WI

  • Chevrolet Silverado 1500 in Bloomington IL

  • Chevrolet Silverado 1500 in Darien IL

  • Old Chevy Trucks for Sale in Darien IL

  • Classic Muscle Cars for Sale in Darien IL

  • Chevrolet Trucks For Sale in Darien IL

  • Cheap Muscle Cars for Sale in Darien IL

  • Work Trucks for Sale in Darien IL

  • Reliable Cars For Sale in Darien IL

  • American Made Trucks For Sale in Darien IL

  • Best Pickup Trucks For Sale in Darien IL

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

  • 2019 Chevrolet Silverado 1500 LT Trail Boss in Darien 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

  • Phillips Chevrolet of Frankfort

  • Chevrolet of Merrillville

  • Ray Chevrolet

  • Jennings Chevrolet

  • Martin Chevrolet

  • Chevrolet of Naperville

  • Phillips Chevrolet of Lansing

  • Napleton Chevrolet St. Charles

  • Castle Chevrolet North of Elk Grove Village

  • Sunrise 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.