Used 2020 Chevrolet Silverado 2500HD for Sale nearChicago, IL

How much does the 2020 Chevrolet Silverado 2500HD cost?

Prices have softened 6.66% compared to this time last year, making it a favorable time to shop this model year.

There are 2,204 listings available, which gives you a solid pool to compare trims and configurations.

If you find a listing below $38,925.54, that's toward the low end of the year-round range and worth acting on quickly.

Is the 2020 Chevrolet Silverado 2500HD a good car?

Yes — 5/5 from users, and 8.17/10 from expert testing. The Silverado 2500HD is presented as a heavy-duty truck that can handle a wide range of roles, with multiple powertrain options and easy-to-use technology.

The model scores 10/10 across Performance and Form and function.

That strength comes with trade-offs: the design may be polarizing, and value for the money is described as poor. For you, that means the truck makes the most sense if capability and straightforward usability matter more than style or bargain pricing.

The market also shows 26.8% of listings as good or great deals, which suggests there are still opportunities if you shop carefully.

Is the 2020 Chevrolet Silverado 2500HD reliable?

Owners rate it 5/5, a strong signal of long-term satisfaction.

The truck is described as modern and straightforward to operate, with a cabin layout that keeps controls familiar and easy to use. Its heavy-duty hardware and multiple powertrain choices also point to a vehicle built for demanding work rather than delicate use.

The diesel powertrain is described as punchy once it builds boost, and the truck’s capability focus suggests it is engineered for sustained towing and hauling. The available maintenance perk language is not present in the provided data.

For used buyers, the main long-term ownership risk is less about complexity and more about how hard the truck was worked before you buy it.

What should I look for when buying a used 2020 Chevrolet Silverado 2500HD?

At 74.1% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.

You should start with a vehicle-history report and then prioritize a thorough pre-purchase inspection, especially if the truck was used for towing or job-site duty. Focus on overall condition, signs of heavy use, and whether the equipment on the truck matches the way you plan to use it.

Key things to evaluate:

• Trim level: The Work Truck comes with a 7-inch touchscreen, a V8 engine, Bluetooth connectivity, and a 3.5-inch digital instrument display, while the LT adds a larger infotainment screen and a power lift-and-lower tailgate. The LTZ adds leather upholstery, heated and cooled front seats, heated rear seats, a heated steering wheel, and remote start, and the High Country adds features such as a spray-on bed liner, front and rear park assist, and a power up-and-down tailgate.
• Powertrain: You get two 6.6-liter V8 options: a gas engine with 401 horsepower and 464 pound-feet of torque, or an optional Duramax turbodiesel V8 with 445 horsepower and 910 pound-feet of torque. Both pair with a 10-speed automatic and available 4WD with low-range gearing.
• Safety package: Safety Package II adds forward-collision avoidance, lane-departure warning, adaptive cruise control, and the Safety Alert Seat. Safety Package I adds front and rear parking sensors and blind-spot monitoring.
• Infotainment: The Work Truck and Custom use a 7-inch touchscreen with Apple CarPlay and Android Auto, while LT, LTZ, and High Country get an 8-inch touchscreen. The truck also offers a 4G LTE WiFi hotspot, and wireless charging is standard on High Country.
• Fuel efficiency: In testing, the truck returned about 17 mpg.

Which 2020 Chevrolet Silverado 2500HD trim should I buy?

The 2020 Chevrolet Silverado 2500HD is offered in 5 trim levels: Work Truck, Custom, LT, LTZ, and High Country.

Here's the short version:

• Work Truck: This is the simplest entry point, but it still gives you a 7-inch touchscreen, Bluetooth, a V8 engine, and a digital instrument display. It makes sense if you want the lowest-frills way into the lineup.
• Custom: This trim adds 20-inch aluminum wheels, LED taillights, a body-color split grille bar, and side-mirror cornering lights. It is the step up if you want more style and a little more equipment without jumping too far in price.
• LT: This is the best-value trim. It adds a chrome grille, upgraded cloth seating, a larger infotainment screen, and a power lift-and-lower tailgate, giving you more comfort and convenience without the big jump to luxury pricing.
• LTZ: This is the comfort-focused choice, especially if you want leather upholstery, heated and cooled front seats, heated rear seats, a heated steering wheel, and remote start. It suits you if you want a more upscale truck and are willing to pay for it.
• High Country: This is the most fully equipped version, with features such as a spray-on bed liner, front and rear park assist, and a power up-and-down tailgate. It is the pick if you want the most premium setup in the lineup.

Safety Package I and Safety Package II add important driver-assistance features, but they are not standard across every trim.

Is now a good time to buy a used 2020 Chevrolet Silverado 2500HD?

The market looks moderate for selective buyers, with enough inventory and enough deal activity to reward comparison shopping.

• Deal availability: 26.8% of listings are priced as good or great deals.
• Inventory: There are 2,204 listings available.
• Price trend: Prices have softened 6.66% compared with last year.
• Clean inventory: 74.1% of listings are accident-free.

If you find a listing below $38,925.54, that's toward the low end of the year-round range and worth acting on quickly.

What is the 2020 Chevrolet Silverado 2500HD's resale value?

The current average of $38,933 sits slightly below last year's $41,712.

That softer pricing suggests the truck has already absorbed some depreciation, which can help you if you buy now and hold it for a while. For a future seller, the current market indicates that condition, configuration, and mileage will matter a lot when it comes time to resell.

Because heavy-duty trucks can vary widely in equipment and use history, well-kept examples should remain easier to move than hard-used ones. The current price trend also gives you a clearer benchmark for judging whether a future trade-in or private-sale offer is fair.

Vehicles with strong owner satisfaction ratings, like this model year's 5/5, tend to retain buyer demand, which supports resale value over time.

Is the 2020 Chevrolet Silverado 2500HD safe?

It earns an 8/10 safety score from our experts.

The Silverado HD comes with a reversing camera, traction control, and a full array of airbags. Safety Package II adds forward-collision avoidance, lane-departure warning, adaptive cruise control, and the Safety Alert Seat, while Safety Package I adds front and rear parking sensors and blind-spot monitoring.

The LTZ improves on the reversing camera with a surround-view camera with trailer views, which is especially useful in a truck this size. For used buyers, the main safety caveat is that some of the most helpful driver-assistance features are package-dependent rather than standard.

Should I buy a 2020 Chevrolet Silverado 2500HD or consider a different year?

If you're weighing the 2020 against nearby model years, here's how to think about it:

Choose the 2020 if:

• 26.8% of listings are priced as good or great deals.
• At 74.1% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.
• Price trend: Prices have softened 6.66% compared with last year.
• Owners rate it 5/5 — a strong satisfaction signal.
• The 2020 model emphasizes multiple powertrain options and easy-to-use technology.

Consider the 2021 if:

• At $41,125, the 2021 costs more than the current year's $38,933 average.
• It broadens appeal with more available options and adds innovative camera technology.

The bottom line: If you want the better value today, the 2020 is the stronger starting point because prices have eased and inventory is healthy. If you are willing to spend more for a newer model with added flexibility and camera tech, the 2021 is worth a look.

These recommendations are based on CarGurus' proprietary market data from August 28, 2026, CarGurus experts' opinions, and generative AI.