Used 2020 Chrysler 300 for Sale nearChicago, IL

How much does the 2020 Chrysler 300 cost?

Prices have softened 9.74% compared to this time last year, making it a favorable time to shop this model year.

There are 624 listings available, which suggests you have a workable amount of inventory to compare.

If you find a listing below $17,792.71, 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 repeatedly praise its smooth and quiet ride, good power, and ample space, and many also like its affordability and distinctive design. That makes it a strong fit if you want a roomy, comfortable large sedan with a classic feel and modern infotainment. With 28.0% of listings marked as good or great deals, you have a meaningful chance to find a competitive price.

Is the 2020 Chrysler 300 reliable?

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

Drivers describe it as well-built, and the recurring praise for good power and a smooth, quiet ride supports the idea that it can be a dependable daily driver. The repeated mention of affordability also suggests it appeals to buyers who want a straightforward ownership experience rather than a complicated one. For used buyers, the main long-term risk is making sure the specific car has been cared for properly, since condition matters more once a model has been on the road for years.

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

At 58.3% 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 pre-purchase inspection that focuses on body condition, alignment, and signs of uneven wear. Because this model’s appeal depends heavily on comfort and overall condition, you should pay close attention to how the cabin, ride quality, and exterior presentation hold up.

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

This looks like a moderate, selective buyer’s market, where you can shop patiently but still move quickly on the right car.

• Deal availability: 28.0% of listings are priced as good or great deals.
• Inventory: There are 624 listings available.
• Price trend: Prices have softened 9.74% compared with last year.
• Clean inventory: 58.3% of listings are accident-free.

If you find a listing below $17,792.71, 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 $18,359 sits slightly below last year's $20,340.

That softer pricing can help you buy more affordably now, but it also means future resale will depend on how well the market continues to value this model’s strengths. If you keep the car in strong condition and avoid examples with accident history, you should be in a better position when it’s time to sell. 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:

• 28.0% of listings are priced as good or great deals.
• At 58.3% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.
• Price trend: Prices have softened 9.74% compared with last year.
• Owners rate it 4.78/5 — a strong satisfaction signal.

Consider the 2021 if:

• At $20,185, the 2021 costs more than the current year's $18,359 average.
• It adds a rare rear-wheel-drive luxury-sedan setup with available all-wheel drive and a 5.7-liter Hemi V8.

The bottom line: If you want the better value, the 2020 is the stronger starting point because it combines lower pricing with solid owner satisfaction. If you’re willing to pay more for a newer model year and want the added appeal of the 2021’s configuration choices, that’s the better secondary path for buyers who prioritize those extras over price.

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