Used 2020 Chrysler 300 for Sale nearChicago, IL

How much does the 2020 Chrysler 300 cost?

Prices have softened 11.13% compared to this time last year, making it a favorable time to shop this model year.

There are 636 listings available, which suggests you have a workable amount of inventory to compare.

If you find a listing below $17,805.72, that's toward the low end of the year-round range and worth acting on quickly.

Is the 2020 Chrysler 300 a good car?

Yes — the 2020 Chrysler 300 earns a 4.78/5 user rating, which points to strong owner satisfaction. Drivers commonly praise its smooth and quiet ride, good power, and ample space, and many also like its affordability and distinctive design. For you, that makes it a strong fit if you want a roomy, comfortable large sedan with a traditional feel rather than a sporty or cutting-edge one. With 26.3% of listings marked as good or great deals, there is still some room to shop selectively.

Is the 2020 Chrysler 300 reliable?

Owners rate it 4.78/5, a strong signal of long-term satisfaction.

The user feedback also points to a well-built sedan that feels smooth, quiet, and dependable in everyday use, with many owners highlighting its durable power and comfortable character. That combination suggests the 2020 Chrysler 300 can be a sensible used buy if you want a car you can count on for regular driving. For used buyers, the main long-term ownership risk is less about the core formula and more about finding a well-kept example with a clean maintenance history.

What should I look for when buying a used 2020 Chrysler 300?

At 59.1% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.

You should start with a vehicle history report so you can separate clean examples from cars with prior damage. After that, prioritize a thorough inspection of body panels, alignment, and interior condition, since those areas can reveal how well a car was repaired or maintained. Because this model is valued for comfort and durability, you should focus on overall condition and evidence of consistent care rather than cosmetic shine alone.

Is now a good time to buy a used 2020 Chrysler 300?

This looks like a moderate, selective buyer’s market, so you can shop with some leverage if you stay patient.

• Deal availability: 26.3% of listings are priced as good or great deals.
• Inventory: There are 636 listings available.
• Price trend: Prices have softened 11.13% compared with last year.
• Clean inventory: 59.1% of listings are accident-free.

If you find a listing below $17,805.72, that's toward the low end of the year-round range and worth acting on quickly.

What is the 2020 Chrysler 300's resale value?

The current average of $18,166 sits slightly below last year's $20,442.

That decline tells you the market has already adjusted downward, which can make future resale a little more challenging if prices keep easing. If you buy now, your best protection is choosing a clean, well-kept example that stands out from the average listing. Strong condition matters even more when a model is already trending lower, because buyers tend to pay up for cars that feel cared for.

Vehicles with strong owner satisfaction ratings, like this model year's 4.78/5, tend to retain buyer demand, which supports resale value over time.

Should I buy a 2020 Chrysler 300 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:

• 26.3% of listings are priced as good or great deals.
• At 59.1% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.
• Price trend: Prices have softened 11.13% compared with last year.
• Owners rate it 4.78/5 — a strong satisfaction signal.

Consider the 2021 if:

• At $20,283, the 2021 costs more than the current year's $18,166 average.
• It adds a rare rear-wheel-drive luxury-sedan setup with available all-wheel drive and a Hemi V8.

The 2020 is the better starting point if you want the lower average price and a market that still offers some deal potential. If you are willing to spend more for the next year’s added configuration flexibility, the 2021 is the better secondary path for buyers who want a broader powertrain choice.

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