Used 2021 Chrysler 300 for Sale nearMilwaukee, WI

How much does the 2021 Chrysler 300 cost?

Prices have softened 9.22% compared to this time last year, making it a favorable time to shop this model year.

There are 504 listings available, which suggests you have a workable amount of inventory to compare.

Is the 2021 Chrysler 300 a good car?

Yes — the 2021 Chrysler 300 earns a 4.6/5 user rating and a 7.7/10 expert rating. The standout strength is Technology at 9/10.

Owners consistently praise the luxurious look, smooth ride, impressive handling, acceleration, and comfort. In practical terms, that lines up well with the 300’s traditional big-sedan feel, rear-wheel-drive layout, and cabin that’s described as comfortable, quiet, and easy to use.

The main trade-off is value: the expert review calls out poor value for money, and some owners mention fuel-efficiency concerns along with the loss of certain features in newer models. Even so, if you want a reasonably priced luxury sedan with presence and a more old-school personality, this model year fits that brief well.

The market also shows 27.8% of listings as good or great deals, which gives you some room to shop selectively.

Is the 2021 Chrysler 300 reliable?

Owners rate it 4.6/5, a strong signal of long-term satisfaction.

The owner feedback points to a car that feels dependable in daily use, with praise centered on comfort, smoothness, and the kind of driving experience you can count on over time. The expert review also describes it as quiet and capable on the road, which supports the idea that it’s built for steady, trouble-free use rather than constant attention.

The ownership picture is helped by the 300’s traditional hardware and long-running design, but used buyers should still pay close attention to maintenance history and feature content, especially on higher-mileage examples.

What should I look for when buying a used 2021 Chrysler 300?

At 64.9% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.

You should start with a vehicle history report and then prioritize a pre-purchase inspection, especially if you’re considering a higher-trim car with more equipment. Focus on condition, accident repairs, and whether the features you want are actually present on the specific listing, since some safety and convenience items are trim- or package-dependent.

Key things to evaluate:

• Trim level: The base 300 Touring uses 17-inch silver alloys and cloth upholstery, while the Touring L adds 18-inch polished alloys and Nappa leather. The 300S stands out with standard 20-inch Black Noise wheels, perforated inserts, accent stitching, and heated front seats, so the lower trim is the one most likely to feel stripped down.
• Powertrain: The 3.6-liter Pentastar V6 makes 292 horsepower in the Touring and Touring L, while the 300S gets 300 horsepower and can be paired with a 5.7-liter V8 with 363 hp and 394 lb-ft of torque. Rear-wheel drive is standard, and all-wheel drive is available on the V6 models.
• Safety package: All Chrysler 300s include active head restraints, airbags, traction and stability control with brake assist, rain brake support, ready alert braking, and hill start assist. Blind-spot monitoring and rear cross-traffic alert are limited to the Touring L and 300S, and the SafetyTec Plus Group adds forward collision warning, automatic emergency braking, adaptive cruise control, automatic high beams, lane departure warning, and rain-sensing wipers.
• Infotainment: The 8.4-inch Uconnect 4C touchscreen is standard across the lineup, and Apple CarPlay and Android Auto are standard too. The Popular Equipment Group adds navigation, a 506-watt amp, nine Alpine speakers, SiriusXM Traffic Plus, surround sound, a trunk-mounted subwoofer, and a dual-pane sunroof.
• Fuel efficiency: The V6 with rear-wheel drive returns 19 mpg city, 30 mpg highway, and 23 mpg combined. All-wheel drive lowers that to 18 mpg city, 27 mpg highway, and 21 mpg combined, while the V8-powered 300S gets 16 mpg city, 25 mpg highway, and 19 mpg combined.

Which 2021 Chrysler 300 trim should I buy?

The 2021 Chrysler 300 is offered in 3 trim levels: 300 Touring, 300 Touring L, 300S.

Here's the short version:

• 300 Touring: This is the value entry point if you want the 300’s core strengths — the roomy, quiet cabin, standard 8.4-inch touchscreen, Apple CarPlay, Android Auto, and the traditional rear-wheel-drive feel — without paying for extras you may not need. It’s the trim that best fits budget-minded shoppers who still want the Chrysler’s upscale presence.
• 300 Touring L: This is the best-value trim for most shoppers because it adds Nappa leather, 18-inch polished alloys, and access to more comfort and safety equipment while staying closer to the model’s reasonable-price appeal. If you want the 300 to feel properly luxurious without jumping to the top trim, this is the one to target.
• 300S: Choose this if you want the most power and the most distinctive look, since it adds 300 horsepower, available V8 power, standard 20-inch wheels, and sportier interior touches. It makes the most sense if you care more about character and performance than maximizing value.

Blind-spot monitoring and rear cross-traffic alert are only available on the Touring L and 300S trims, and the SafetyTec Plus Group is where you’ll find the broader driver-assistance suite.

Is now a good time to buy a used 2021 Chrysler 300?

This is a moderate, selective buyer’s market, so you can shop carefully and still find worthwhile listings.

• Deal availability: 27.8% of listings are priced as good or great deals.
• Inventory: There are 504 listings available.
• Price trend: Prices have softened 9.22% compared with last year.
• Clean inventory: 64.9% of listings are accident-free.

If you find a listing below $19,641, that's toward the low end of the year-round range and worth acting on quickly.

What is the 2021 Chrysler 300's resale value?

The current average of $19,646 sits slightly below last year's $21,641.

That decline suggests the market has softened, which can be good news if you’re buying now but less favorable if you’re planning to sell soon. A lower current price can help attract shoppers, but it also means your near-term resale upside may be more limited than it was a year ago.

Even so, the 300’s distinctive positioning as a rear-wheel-drive luxury sedan helps it stand out from more common alternatives. If you keep the car in good condition and maintain it well, that uniqueness can help support demand when it’s time to sell.

Vehicles with strong owner satisfaction ratings, like this model year's 4.6/5, tend to retain buyer demand, which supports resale value over time.

Is the 2021 Chrysler 300 safe?

The 2021 Chrysler 300 earns Good IIHS crash-test results in most categories, but it also receives a Marginal score in the small overlap tests and a Poor rating for headlights. It earns four-star ratings in frontal crash and rollover, and five-star ratings in all other NHTSA tests.

It earns a 7/10 safety score from our experts.

All Chrysler 300s include active head restraints, airbags, traction and stability control with brake assist, rain brake support, ready alert braking, and hill start assist. If you want more advanced driver assistance, you need to move up to the Touring L or 300S for blind-spot monitoring and rear cross-traffic alert, and then add the SafetyTec Plus Group for forward collision warning, automatic emergency braking, adaptive cruise control, automatic high beams, lane departure warning, and rain-sensing wipers.

The main caveat is that some of the more desirable safety tech is not standard, so you should verify exactly which packages are on the used car you’re considering.

Should I buy a 2021 Chrysler 300 or consider a different year?

If you're weighing the 2021 against nearby model years, here's how to think about it:

Choose the 2021 if:

• 27.8% of listings are priced as good or great deals.
• At 64.9% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.
• Price trend: Prices have softened 9.22% compared with last year.
• Owners rate it 4.6/5 — a strong satisfaction signal.
• The 2021 model keeps the 300’s classic rear-wheel-drive luxury-sedan character, with a comfortable cabin, easy-to-use tech, and available V8 power.

The bottom line: If you want the 300’s traditional big-sedan feel at a lower used price, the 2021 is a strong place to start. If you’re especially price-sensitive, you can also compare nearby years, but the 2021 stands out for its mix of value, comfort, and available equipment.

How does the 2021 Chrysler 300 compare to the 2021 Dodge Charger?

Expert Pros & Cons (per CarGurus review team)

2021 Chrysler 300:

• Pros: Comfortable, Quiet cabin, Easy-to-use technology.
• Cons: Poor value for money.

2021 Dodge Charger:

• Pros: Multiple powertrain options, Fun to drive, Powerful engine.
• Cons: Cramped back seat, Underwhelming base engine, Outdated technology.

Our experts score the 2021 Chrysler 300 7.7/10 and the 2021 Dodge Charger 7.8/10. The Charger edges ahead on overall score and brings more powertrain variety, but the 300 counters with a quieter cabin and easier-to-use technology. If you want a more relaxed, comfort-first full-size sedan, the 300 makes sense; if you want a more performance-oriented choice, the Charger has the advantage.

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

These recommendations are based on CarGurus' proprietary market data from October 21, 2026, CarGurus experts' opinions, and generative AI.