CarGurus Header

Used Chevrolet Silverado 1500 Custom Trail Boss for Sale nearFreeport, IL

Filters (3)

Location:

Only show listings in IL?

Include delivery listings?

142 vehicles found

Year:
2019
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
4.3L V6 Flex Fuel Vehicle
Exterior color:
Black
Combined gas mileage:
17 MPG
Fuel type:
Flex Fuel Vehicle
Interior color:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
185,813
Stock #:
50144A
VIN:
1GCPYCEH8KZ398032
Black 2019 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive
New arrival
Ray Chevrolet

Sponsored by Ray Chevrolet

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

185,813 mi

Fox Lake, IL
74 mi away
Good Deal

$18,296

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:
6-Speed Automatic Overdrive
Mileage:
68,263
Stock #:
GQ32316
VIN:
3GCPYCEF2MG146410
Black 2021 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive

Sponsored Listing

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

68,263 mi

Gurnee, IL
85 mi away
Good Deal

$33,076

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:
Dark Ash Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
9,296
Stock #:
Q12057
VIN:
3GCUDCED8RG199987
Dark Ash Metallic 2024 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic
New arrival

Sponsored Listing

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

9,296 mi

Dubuque, IA
56 mi away
Fair Deal

$45,799

Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Red Hot
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
58,290
Stock #:
P1836
VIN:
3GCPYCEK8NG208262
Red Hot 2022 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 8-Speed Automatic

 

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

58,290 mi

Schaumburg, IL
83 mi away
Good Deal

$32,313

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:
6-Speed Automatic Overdrive
Mileage:
60,392
Stock #:
K8764
VIN:
1GCPYCEF1MZ239290
Black 2021 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive

 

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

60,392 mi

East Dundee, IL
72 mi away
Fair Deal

$35,363

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:
Dark Ash Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
19,917
Stock #:
T260603A
VIN:
3GCUDCED8RG106353
Dark Ash Metallic 2024 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic
New arrival

 

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

19,917 mi

Dubuque, IA
56 mi away
Fair Deal

$44,515

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:
Dark Ash Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
25,278
Stock #:
J5734A
VIN:
3GCPDCEK6NG565726
Dark Ash Metallic 2022 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 8-Speed Automatic
New arrival

 

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

25,278 mi

Naperville, IL
83 mi away
Fair Deal

$37,790

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:
Dark Ash Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
9,296
Stock #:
Q12057
VIN:
3GCUDCED8RG199987
Dark Ash Metallic 2024 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic
New arrival

 

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

9,296 mi

Dubuque, IA
56 mi away
Fair Deal

$45,799

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
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic
Mileage:
157,898
VIN:
1GCRYCEF4KZ345075
Black 2019 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 6-Speed Automatic

 

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

157,898 mi

Portage, WI
84 mi away
Good Deal

$18,999

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:
Glacier Blue Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
81,354
Stock #:
N25159A
VIN:
3GCPDCED6NG679176
Glacier Blue Metallic 2022 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

81,354 mi

Elk Grove Village, IL
87 mi away
Fair Deal

$33,390

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:
Black
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
41,920
Stock #:
Q11973
VIN:
3GCUDCED7PG127837
Black 2023 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

41,920 mi

Dubuque, IA
56 mi away
Good Deal

$39,812

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:
45,678
Stock #:
P6036
VIN:
3GCUDCED1PG323353
Summit White 2023 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

45,678 mi

Elmhurst, IL
90 mi away
Good Deal

$38,903

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:
54,995
Stock #:
PTS169870A
VIN:
3GCPYCEF7MG105075
Black 2021 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

54,995 mi

Madison, WI
51 mi away
Good Deal

$34,879

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:
Mosaic Black Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
54,771
Stock #:
5048
VIN:
1GCPYCEL5NZ100710
Mosaic Black Metallic 2022 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

54,771 mi

Home delivery from Seffner, FL
Price includes $1,125 shipping
Great Deal

$33,119

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:
Jet Black
Transmission:
Automatic
Mileage:
82,669
Stock #:
L265819A
VIN:
3GCPDCED9NG674473
Black 2022 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic
New arrival

 

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

82,669 mi

Home delivery from Collinsville, IL
Price includes $378 shipping
Fair Deal
Manufacturer certified

$34,373

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
Transmission:
6-Speed Automatic Overdrive
Mileage:
33,262
Stock #:
MX4598
VIN:
1GCPYCEF4MZ232253
Black 2021 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive
New arrival

 

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

33,262 mi

Home delivery from Michigan Center, MI
Price includes $490 shipping
Fair Deal

$37,123

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:
Gray
Transmission:
6-Speed Automatic Overdrive
Mileage:
62,775
Stock #:
5019
VIN:
1GCPYCEF0LZ168095
Black 2020 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive

 

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

62,775 mi

Home delivery from Burton, MI
Price includes $307 shipping
Great Deal

$29,707

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:
49,669
Stock #:
28739643
VIN:
1GCPYCEK8NZ237762
Black 2022 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic
New arrival

 

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

49,669 mi

Store transfer to Madison, WI
Price includes $1,499 shipping
Fair Deal

$36,497

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:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
110,080
Stock #:
935390B
VIN:
1GCPYCEF5KZ366976
Black 2019 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive

 

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

110,080 mi

Maquoketa, IA
56 mi away
Good Deal

$26,063

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:
Summit White
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
53,768
Stock #:
PM174391
VIN:
1GCPYCEL0NZ174391
Summit White 2022 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

53,768 mi

Home delivery from Pleasantville, NJ
Price includes $1,502 shipping
Great Deal

$36,242

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:
Gray
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Transmission:
6-Speed Automatic Overdrive
Mileage:
69,122
Stock #:
406-B598
VIN:
1GCPYCEF5KZ375743
Gray 2019 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive

 

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

69,122 mi

Home delivery from Huntington, IN
Price includes $708 shipping
Good Deal

$31,964

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:
Black
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
32,963
Stock #:
MK260223A
VIN:
3GCUDCED0RG150847
Black 2024 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

32,963 mi

McHenry, IL
69 mi away
Fair Deal

$42,410

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:
Glacier Blue Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
JET BLACK
Transmission:
Automatic
Mileage:
89,467
Stock #:
P581637B
VIN:
3GCPDCED8NG581637
Glacier Blue Metallic 2022 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

89,467 mi

Home delivery from Livingston, TX
Price includes $1,276 shipping
Fair Deal

$34,552

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:
44,616
Stock #:
P7412
VIN:
3GCUDCEDXPG304686
Summit White 2023 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic
New arrival

Sponsored Listing

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

44,616 mi

Crystal Lake, IL
68 mi away
Fair Deal

$41,190

FAQs

How much does the Chevrolet Silverado 1500 Custom Trail Boss cost in Freeport, IL?
The average Chevrolet Silverado 1500 Custom Trail Boss costs about $27,150.94. The average price has decreased by -1.4% since last year. The 110 for sale near Freeport, IL on CarGurus, range from $17,987 to $56,180 in price.
How many Chevrolet Silverado 1500 Custom Trail Boss vehicles in Freeport, IL have no reported accidents or damage?
91 out of 110 for sale near Freeport, IL have no reported accidents or damage.
What is the fuel economy of the Chevrolet Silverado 1500 Custom Trail Boss?
Depending on the engine and options, the Chevrolet Silverado 1500 Custom Trail Boss gets between 15 and 24 MPG (or EV battery range).
What fuel types are available?
Diesel, Flex Fuel Vehicle, Gasoline engines are available.

Relevant articles

A better way to discover your best deal

Let us help you find a car you’ll love.

CarGurus Footer