Used 2021 Chevrolet Silverado 2500HD for Sale nearChicago, IL

How much does the 2021 Chevrolet Silverado 2500HD cost?

Prices have softened 4.62% compared to this time last year, making it a favorable time to shop this model year.

There are 2,896 listings available, which gives you a solid pool to compare prices and equipment.

If you find a listing below $41,133.82, that's toward the low end of the year-round range and worth acting on quickly.

Is the 2021 Chevrolet Silverado 2500HD a good car?

Yes — the 2021 Chevrolet Silverado 2500HD earns a 4.67/5 user rating and a 6.83/10 expert rating.

The model scores 8/10 across Performance, Form and function, and Technology.

Owners consistently praise its impressive power, spacious interior, and robust features. They also point to the comfortable ride and the 6.6 gas engine as standout strengths.

The trade-offs are familiar for a heavy-duty truck: the interior materials feel cheaper than you might want, and some owners mention missing extras and minor cosmetic issues.

That fits the truck’s use case well: you’re getting a capable heavy-duty pickup with multiple body styles and powertrain choices, but not a luxury-grade cabin.

With 27.6% of listings marked as good or great deals, you have room to shop selectively.

Is the 2021 Chevrolet Silverado 2500HD reliable?

Owners rate it 4.67/5, a strong signal of long-term satisfaction.

Owner feedback points to a truck that feels dependable, with praise for its power, comfortable ride, and robust feature set. The summary also highlights a spacious interior and a generally trouble-free ownership impression, even if some buyers noticed cheaper interior materials and minor cosmetic issues.

The truck’s performance notes reinforce that sense of durability, especially for buyers who plan to tow or use it hard. Chevrolet also includes a hitch, seven-pin connector, trailering mirrors, a rearview camera, and hitch-guidance technology as standard equipment, which supports everyday dependability.

For used buyers, the main long-term ownership risk is less about outright weakness and more about finding a well-kept example that hasn’t been worn down by heavy-duty use.

What should I look for when buying a used 2021 Chevrolet Silverado 2500HD?

Accident-free inventory is solid at 77.8% — always verify the vehicle history report.

You should still run a history report on every truck you consider, because heavy-duty pickups often lead hard lives. Prioritize a pre-purchase inspection that focuses on signs of towing wear, bed and step damage, and cabin wear. Pay close attention to whether the truck has the equipment you want, since this model can vary a lot by trim and package.

Key things to evaluate:

• Trim level: Work Truck and Custom are the most basic versions, while LT, LTZ, and High Country add more comfort and convenience. Base-trim trucks can feel sparse, so check carefully for the features you want before you buy.
• Powertrain: You can choose a 6.6-liter V8 gasoline engine or a 6.6-liter Duramax turbodiesel. The gas engine makes 401 horsepower and 464 pound-feet of torque, while the diesel makes 445 hp and 910 lb-ft of torque and is the stronger choice for towing.
• Safety package: Work Truck and Custom can be equipped with a Safety Confidence Package that adds forward-collision warning, automatic emergency braking, steering-wheel audio controls, a 4.2-inch driver information screen, and cruise control.
• Infotainment: Every truck gets a 7-inch touchscreen, Apple CarPlay, Android Auto, and Bluetooth. Wireless Apple CarPlay and wireless Android Auto are available, along with an 8-inch infotainment touchscreen and a bed view camera.
• Fuel efficiency: Fuel-economy figures are not provided for this heavy-duty truck.

Which 2021 Chevrolet Silverado 2500HD trim should I buy?

The 2021 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 most basic choice, and it makes sense if you want the lowest-frills path into the Silverado HD lineup. It gets the core truck hardware, but you should expect a fleet-like feel.
• Custom: This is the better pick if you want a little more equipment without moving too far up the price ladder. It can also be equipped with the Safety Confidence Package, which makes it a smarter value than the Work Truck for many buyers.
• LT: This is the best-value trim for most shoppers because it adds more everyday usability and can be paired with useful options like Duramax and Appearance Packages. It also gets the EZ Lift tailgate standard.
• LTZ: This is the step-up choice if you want a more upscale feel and more available equipment without jumping all the way to the top trim.
• High Country: This is the luxury-leaning version, and it makes the most sense if you want the most premium Silverado HD experience and are willing to pay for it.

Work Truck and Custom are the trims that can be equipped with the Safety Confidence Package.

Is now a good time to buy a used 2021 Chevrolet Silverado 2500HD?

This looks like a moderate, selective buyer’s market, so you can shop carefully and still find room to negotiate.

• Deal availability: 27.6% of listings are priced as good or great deals.
• Inventory: There are 2,896 listings available.
• Price trend: Prices have softened 4.62% compared with last year.
• Clean inventory: 77.8% of listings are accident-free.

If you find a listing below $41,133.82, that's toward the low end of the year-round range and worth acting on quickly.

What is the 2021 Chevrolet Silverado 2500HD's resale value?

The current average of $41,125 sits slightly below last year's $43,118.

That softer pricing suggests the truck has already absorbed some depreciation, which can help future resale stability if you buy at the right price. For a heavy-duty pickup, strong capability and broad buyer appeal can support demand later, especially if you choose a well-equipped, well-kept example.

The market also shows enough inventory to give you leverage now, which matters because buying below the current average can improve your eventual resale position. Trucks with strong owner satisfaction ratings, like this model year's 4.67/5, tend to retain buyer demand, which supports resale value over time.

Is the 2021 Chevrolet Silverado 2500HD safe?

The National Traffic Safety Administration (NHTSA) and Insurance Institute for Highway Safety (IIHS) don't crash test heavy-duty trucks.

It earns a 5/10 safety score from our experts.

Chevrolet equips every Silverado 2500 with six airbags, a rearview camera, Teen Driver software, electronic stability control with traction control, and a tire-pressure monitoring system.

Work Truck and Custom models are eligible for the Safety Confidence Package, which adds forward-collision warning, automatic emergency braking, steering-wheel audio controls, a 4.2-inch driver information screen, and cruise control.

Additional available safety features include front and rear park assist, lane-departure warning, OnStar and Chevrolet Connected Services, rear-seat reminder, high-beam assist, and following distance indicator.

Should I buy a 2021 Chevrolet Silverado 2500HD or consider a different year?

If you're weighing the 2021 against nearby model years, here's how to think about it:

Choose the 2021 if:

• 27.6% of listings are priced as good or great deals.
• Accident-free inventory is solid at 77.8% — always verify the vehicle history report.
• Price trend: Prices have softened 4.62% compared with last year.
• Owners rate it 4.67/5 — a strong satisfaction signal.
• The 2021 adds fresh camera technology and wireless Apple CarPlay and Android Auto availability.

Consider the 2020 if:

• At $38,933, the 2020 costs less than the current year's $41,125 average.
• It offers capable towing and easy-to-use technology.

The bottom line: If you want the better-balanced shopping environment, the 2021 is the stronger pick because pricing has eased and inventory is healthy. If your priority is spending less up front, the 2020 is the better value path, especially if you find one in good condition with the equipment you want.

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