Used 2020 Chrysler 300 for Sale nearMilwaukee, WI

How much does the 2020 Chrysler 300 cost?

Prices have softened 7.54% compared to this time last year, making it a favorable time to shop this model year.

There are 563 listings available, which gives you a solid pool to compare prices and condition.

Is the 2020 Chrysler 300 a good car?

Yes — the 2020 Chrysler 300 earns a 4.8/5 user rating, which points to strong owner satisfaction.

Drivers consistently praise its smooth and quiet ride, good power, and ample space. The review summary also highlights its well-built feel, affordability, and distinctive design, which fits the 300’s role as a roomy, traditional sedan with a comfortable cabin and a premium feel.

With its broad appeal as a large, comfortable sedan, it makes sense if you want a full-size car that leans into classic strengths rather than the latest trends. The market also shows 31.4% of listings as good or great deals, which suggests there are still worthwhile opportunities if you shop carefully.

Is the 2020 Chrysler 300 reliable?

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

The review summary points to a well-built sedan that many drivers describe as dependable, with a smooth ride and the kind of trouble-free character shoppers often want in a long-term daily driver. It also gets credit for its durable powertrain lineup and solid build quality.

For used buyers, that combination suggests manageable long-term ownership risk if you choose a clean, well-maintained example and verify its history before you buy.

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

At 56.8% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.

You should run a vehicle history report before you commit, then prioritize a pre-purchase inspection so you can catch hidden body, suspension, or repair issues. Focus closely on overall condition, because a large sedan like this can vary a lot depending on how it was driven and maintained.

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 patiently and still find value.

• Deal availability: 31.4% of listings are priced as good or great deals.
• Inventory: There are 563 listings available.
• Price trend: Prices have softened 7.54% compared with last year.
• Clean inventory: 56.8% of listings are accident-free.

If you find a listing below $17,594, 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 $17,594 sits slightly below last year's $19,030.

That price movement suggests the model has softened, which can help you buy at a more favorable entry point today. For a future seller, that also means resale value may depend more heavily on condition, mileage, and how well the car has been maintained.

Because the 300 still has strong owner satisfaction and a distinctive full-size sedan appeal, clean examples should continue to attract interest better than neglected ones.

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 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:

• 31.4% of listings are priced as good or great deals.
• At 56.8% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.
• Price trend: Prices have softened 7.54% compared with last year.
• Owners rate it 4.8/5 — a strong satisfaction signal.

Consider the 2021 if:

• At $19,661, the 2021 costs more than the current year's $17,594 average.
• It adds a more upscale-feeling daily-driver experience with comfort-focused appeal.

The bottom line: You should start with the 2020 if you want the better value and are comfortable shopping carefully for condition. Move to the 2021 if you’re willing to pay more for a newer example and a slightly more refined ownership experience.

How does the 2020 Chrysler 300 compare to the 2020 Dodge Charger?

Read our full side-by-side expert comparison here.

These recommendations are based on CarGurus' proprietary market data from November 10, 2026, CarGurus experts' opinions, and generative AI.