Used 2019 Chevrolet Silverado 2500HD for Sale nearChicago, IL

How much does the 2019 Chevrolet Silverado 2500HD cost?

Prices have softened 4.82% compared to this time last year, making it a favorable time to shop this model year.

There are 1,897 listings available, which suggests solid inventory for comparison shopping.

If you find a listing below $33,848.44, that's toward the low end of the year-round range and worth acting on quickly.

Is the 2019 Chevrolet Silverado 2500HD a good car?

Yes — the 2019 Chevrolet Silverado 2500HD earns a 4.8/5 user rating, which points to strong owner satisfaction.

Drivers repeatedly praise its performance, especially the Duramax diesel engine, along with its towing and hauling capability. The cabin also gets credit for being more usable and more refined than older heavy-duty trucks, which matters if you want a truck that can work hard without feeling stripped down. For you, that makes it a strong fit if you need serious capability but still want a truck that is easier to live with day to day.

29.6% of listings are priced as good or great deals, so you still have room to shop selectively.

Is the 2019 Chevrolet Silverado 2500HD reliable?

Owners rate it 4.8/5, a strong signal of long-term satisfaction.

Reviewers describe it as dependable and capable, and they specifically connect that reputation to towing and hauling use. The feedback also points to a truck that owners feel comfortable counting on for demanding work, which is exactly the kind of confidence used buyers want in a heavy-duty pickup.

For you, the main long-term ownership risk is buying a truck that has been worked hard without a clear maintenance and condition history.

What should I look for when buying a used 2019 Chevrolet Silverado 2500HD?

At 72.3% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.

You should start with a vehicle history report and confirm whether any damage was structural, cosmetic, or repaired properly. Then prioritize a thorough inspection of the truck’s frame, suspension, brakes, tires, and towing-related wear, since heavy-duty use can hide more than it shows. Focus on overall condition and maintenance records, because a well-kept truck is far more important than mileage alone in this segment.

Is now a good time to buy a used 2019 Chevrolet Silverado 2500HD?

This is a moderate, selective buyer’s market, so you can shop patiently but should move quickly on the right truck.

• Deal availability: 29.6% of listings are priced as good or great deals.
• Inventory: There are 1,897 listings available.
• Price trend: Prices have softened 4.82% compared with last year.
• Clean inventory: 72.3% of listings are accident-free.

If you find a listing below $33,848.44, that's toward the low end of the year-round range and worth acting on quickly.

What is the 2019 Chevrolet Silverado 2500HD's resale value?

The current average of $34,020 sits slightly below last year's $35,745.

That kind of price movement suggests the market has cooled a bit, which can help you buy more confidently now but may also limit upside if you plan to sell soon. For a future seller, the key takeaway is that resale value will depend heavily on condition, mileage, and whether the truck has a clean history. Heavy-duty trucks with strong owner demand tend to hold attention better, especially when they have a reputation for capability and durability.

Vehicles with strong owner satisfaction ratings, like this model year's 4.8/5, tend to retain buyer demand, which supports resale value over time.

Should I buy a 2019 Chevrolet Silverado 2500HD or consider a different year?

If you're weighing the 2019 against nearby model years, here's how to think about it:

Choose the 2019 if:

• 29.6% of listings are priced as good or great deals.
• At 72.3% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.
• Price trend: Prices have softened 4.82% compared with last year.
• Owners rate it 4.8/5 — a strong satisfaction signal.

Consider the 2020 if:

• At $39,054, the 2020 costs more than the current year's $34,020 average.
• It pushes capability and tech even further, but at a noticeably higher price.

The bottom line: You should lean toward the 2019 if you want strong capability, good owner satisfaction, and a more approachable price. If you’re price-sensitive, the 2019 is the smarter path; if you’re willing to pay more for the next model year’s added capability and tech emphasis, the 2020 is worth a look.

These recommendations are based on CarGurus' proprietary market data from September 4, 2026, CarGurus experts' opinions, and generative AI.