Skip to content

Used Chevrolet Silverado 1500 Custom Trail Boss for Sale in

Buy Online
Buy your next car 100% online through TrueCar+ with transparent pricing, no hidden fees and home delivery
Popular filters
Vehicle Condition
Brand
Chicago, IL
Value: 75 miles
Min: 75 milesMax: 75 miles
Include non-local listings
Price
Price drop
Condition

Vehicle history data is provided by Experian AutoCheck. Use of this data is subject to the AutoCheck Terms & Conditions.

POPULAR exterior colors
POPULAR interior colors
Body style
Features
Fuel type
Transmission
Drivetrain
Reset all
63 Listings
Clear all

Find a Used Chevrolet Silverado 1500 Custom Trail Boss in Chicago, IL

TrueCar has 63 used Chevrolet Silverado 1500 Custom Trail Boss models for sale in Chicago, IL, including a Chevrolet Silverado 1500 Custom Trail Boss Crew Cab Short Bed 4WD and a Chevrolet Silverado 1500 Custom Trail Boss Double Cab Standard Box 4WD. Prices for a used Chevrolet Silverado 1500 Custom Trail Boss in Chicago, IL currently range from $20,000 to $59,900, with vehicle mileage ranging from 42 to 174,974.

Nationwide Chevrolet Silverado 1500 Listings by Year

Chevrolet Silverado 1500 Owner Reviews

4th Generation Chevrolet Silverado 1500

2019 - Present
Overall Rating
4.8
10 out of 10
Based on 902 Ratings
Performance
4.8
Comfort
4.6
Fuel Efficiency
4.1
Safety Technology
4.3
Features
4.5
All reviews
3.06 out of 10
Performance
3.0
Comfort
2.0
Fuel Efficiency
3.0
Safety Technology
3.0
Features
1.0
Performance
3.0
Comfort
2.0
Fuel Efficiency
3.0
Safety Technology
3.0
Features
1.0
pros
It's short and easy to park.
cons
There are things I would have liked to have, but I bought what I could afford.
Submitted by Anonymous Author on --- --- ----|2024 Chevrolet Silverado 1500 WT Regular Cab Standard Bed 4WD
5.010 out of 10
Performance
5.0
Comfort
5.0
Fuel Efficiency
5.0
Safety Technology
5.0
Features
5.0
pros
Multifunction tailgate.
cons
No dislikes.
Submitted by Tf on --- --- ----|2025 Chevrolet Silverado 1500 High Country Crew Cab Short Bed 4WD
5.010 out of 10
Performance
5.0
Comfort
4.0
Fuel Efficiency
2.0
Safety Technology
5.0
Features
4.0
pros
The power.
cons
Mpg.
Submitted by Anonymous Author on --- --- ----|2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab Short Bed 4WD