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 Buffalo Grove, IL

145 results
Buffalo Grove, IL
2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Jidd Motors Mitsubishi

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

18,119 miles

$42,595

Fair Deal
Des Plaines, IL
9 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

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

139,582 miles

$24,995

Fair Deal
Elgin, IL
18 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:
White
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
139,582
Stock number:
287527
VIN:
1GCPYCEF4MZ287527

Sponsored

2019 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

76,910 miles

$27,950

Fair Deal
East Dundee, IL
17 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:
Silver Ice
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
76,910
Stock number:
26062A
VIN:
1GCPYCEFXKZ273936

Sponsored

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
30 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

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
21 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

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

106,663 miles

$26,976

Fair Deal
Saint Charles, IL
25 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:
106,663
Stock number:
F4745
VIN:
3GCPYCEF9LG153286

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

85,764 miles

$29,626

Good Deal
Kenosha, WI
28 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:
Summit White
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
85,764
Stock number:
K260109A
VIN:
1GCPYCEF1LZ177050

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

113,155 miles

$25,410

Fair Deal
McHenry, IL
19 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:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
113,155
Stock number:
MC260072A
VIN:
3GCPYCEF4KG237577

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
19 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

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

51,071 miles

$30,000

Fair Deal
Mchenry, 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:
Cajun Red Tintcoat
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
51,071
Stock number:
UT20663
VIN:
1GCRYCEF4KZ312867

Preparing for a close up...

Photos coming soon

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

31,600 miles

$43,900

Fair Deal
Wheeling, IL
2 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:
Summit White
Fuel type:
Diesel
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
31,600
Stock number:
W175491A
VIN:
3GCUKCE80SG109486

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

114,389 miles

$21,997

Great Deal
Arlington Heights, IL
3 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:
Red Hot
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
114,389
Stock number:
AN3717A
VIN:
1GCPYCEF4KZ218947

Sponsored

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

  • Chevrolet Silverado 1500 RST in Buffalo Grove IL

  • Chevrolet Silverado 1500 LTZ in Buffalo Grove IL

  • Chevrolet Silverado 1500 LT Trail Boss in Buffalo Grove IL

  • Chevrolet Silverado 1500 LT1 in Buffalo Grove IL

  • Chevrolet Silverado 1500 Custom in Buffalo Grove IL

  • Chevrolet Silverado 1500 High Country in Buffalo Grove IL

  • Chevrolet Silverado 1500 Custom Trail Boss in Buffalo Grove IL

  • Chevrolet Silverado 1500 Work Truck in Buffalo Grove IL

  • Chevrolet Silverado 1500 in Palatine IL

  • Chevrolet Silverado 1500 in Chicago IL

  • Chevrolet Silverado 1500 in Kenosha WI

  • Chevrolet Silverado 1500 in Aurora IL

  • Chevrolet Silverado 1500 in Rockford IL

  • Chevrolet Silverado 1500 in Milwaukee WI

  • Chevrolet Silverado 1500 in Janesville WI

  • Chevrolet Silverado 1500 in South Bend IN

  • Chevrolet Silverado 1500 in Madison WI

  • Chevrolet Silverado 1500 in Buffalo Grove IL

  • Old Chevy Trucks for Sale in Buffalo Grove IL

  • Classic Muscle Cars for Sale in Buffalo Grove IL

  • Chevrolet Trucks For Sale in Buffalo Grove IL

  • Cheap Muscle Cars for Sale in Buffalo Grove IL

  • Work Trucks for Sale in Buffalo Grove IL

  • Reliable Cars For Sale in Buffalo Grove IL

  • American Made Trucks For Sale in Buffalo Grove IL

  • Best Pickup Trucks For Sale in Buffalo Grove IL

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

  • 2019 Chevrolet Silverado 1500 Custom Trail Boss in Buffalo Grove 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 Bolingbrook

  • Advantage Chevrolet Hodgkins

  • Phillips Chevrolet of Frankfort

  • Ray Chevrolet

  • Jennings Chevrolet

  • Martin Chevrolet

  • Chevrolet of Naperville

  • Castle Chevrolet North of Elk Grove Village

  • Phillips Chevrolet of Lansing

  • Napleton Chevrolet St. Charles

  • Sunrise Chevrolet

  • Golf Mill 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.