Used 2019 Chevrolet Silverado 3500HD for Sale nearChicago, IL

How much does the 2019 Chevrolet Silverado 3500HD cost?

Prices have softened 7.50% compared to this time last year, making it a favorable time to shop this model year.

There are 576 listings available, which suggests you have a workable amount of inventory to compare.

Is the 2019 Chevrolet Silverado 3500HD a good car?

Yes — 5/5 is a strong user rating for this model year. The 2019 Chevrolet Silverado 3500HD stands out as a heavy-duty truck that blends serious capability with a more modern feature set than many buyers expect from a work-focused rig. It also offers useful technology for its era, including an available digital driver display, touchscreen infotainment, Wi-Fi hotspot capability, and driver-assist features such as lane departure warnings and forward collision alerts.

For you, that means this truck makes the most sense if you want a work-focused heavy-duty pickup that still feels reasonably up to date inside. 29.0% of listings are priced as good or great deals, which gives you some room to shop selectively.

Is the 2019 Chevrolet Silverado 3500HD reliable?

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

The 2019 Chevrolet Silverado 3500HD is described as having a mixed reputation for reliability, so condition and maintenance history matter more here than they might on a lighter-duty truck. Because this is a heavy-duty model built for demanding use, you should expect ownership risk to rise if prior maintenance was inconsistent or if the truck was worked hard without careful upkeep.

What should I look for when buying a used 2019 Chevrolet Silverado 3500HD?

At 67.9% 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 prior damage was repaired properly. Then prioritize a thorough pre-purchase inspection, with extra attention to signs of hard use, uneven wear, and any evidence that the truck was used for towing or hauling beyond what the seller discloses. Focus on overall condition and maintenance records, since those details matter a lot on a heavy-duty truck.

Is now a good time to buy a used 2019 Chevrolet Silverado 3500HD?

This looks like a moderate, selective buyer’s market, so you can shop carefully without feeling rushed.

• Deal availability: 29.0% of listings are priced as good or great deals.
• Inventory: There are 576 listings available.
• Price trend: Prices have softened 7.50% compared with last year.
• Clean inventory: 67.9% of listings are accident-free.

If you find a listing below $39,857, that's toward the low end of the year-round range and worth acting on quickly.

What is the 2019 Chevrolet Silverado 3500HD's resale value?

The current average of $40,412 sits slightly below last year's $43,689.

That price movement suggests the market has cooled, which can help you buy more selectively now but may also limit upside if you plan to resell soon. For a future seller, the key is to buy well and keep the truck in strong condition, because heavy-duty trucks can hold buyer interest when they present as well maintained and ready for work.

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

Should I buy a 2019 Chevrolet Silverado 3500HD 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:

• 29.0% of listings are priced as good or great deals.
• At 67.9% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.
• Price trend: Prices have softened 7.50% compared with last year.
• Owners rate it 5/5 — a strong satisfaction signal.

The bottom line: If you want a heavy-duty truck with strong capability, useful tech, and a market that currently gives you some negotiating room, the 2019 is the primary path to consider. If you are especially price-sensitive, you should also compare nearby years and focus on the cleanest, best-documented truck rather than chasing the lowest sticker alone.

These recommendations are based on CarGurus' proprietary market data from September 15, 2026, CarGurus experts' opinions, and generative AI.