Used 2021 Chrysler 300 for Sale nearChicago, IL

How much does the 2021 Chrysler 300 cost?

Prices have softened 7.20% compared to this time last year, making it a favorable time to shop this model year.

There are 491 listings available, which gives you a modest 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 use, that lines up with the car’s roomy, traditional full-size sedan character and its easy-to-use tech.

The main trade-off is value for money, and the expert review also points to the model’s age and its less modern feel versus newer rivals. For you, that means the 300 makes the most sense if you want comfort, presence, and a distinctive layout more than the latest bargain or the newest design.

32.0% of listings are marked as good or great deals, so there is some room to shop carefully.

Is the 2021 Chrysler 300 reliable?

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

The owner summary points to a car that feels luxurious, smooth, and dependable in everyday use, with praise for its ride quality, handling, and acceleration. That kind of feedback suggests the 300 is the sort of sedan you can count on for comfortable long-term ownership if it has been maintained well.

The expert review also describes it as quiet, capable, and comfortable on the road, which reinforces the idea that it is built around steady daily usability rather than flash. For used buyers, the main long-term risk is less about the concept and more about finding one that has been cared for properly, since age and feature content can vary a lot by trim and package.

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

At 62.1% 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 are considering a higher-trim car with more equipment. Focus on overall condition, signs of prior bodywork, and whether the features you want are actually present on the specific car you are looking at.

Key things to evaluate:

• Trim level: The base 300 Touring uses 17-inch silver alloys, cloth upholstery, and a simpler lighting setup, while the Touring L adds Nappa leather and more upscale equipment. The 300S brings 20-inch Black Noise wheels, perforated inserts, accent stitching, and a more premium feel, so the lower trims are the ones where you will notice the biggest feature gaps.
• 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 but not the 300S.
• Safety package: All 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 or 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 system is a strong point, and the available Popular Equipment Group adds navigation, a premium Alpine audio setup, SiriusXM Traffic Plus, surround sound, 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 returns 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 entry point, and it gives you the core 300 experience: rear-wheel drive, the 292-hp V6, the 8.4-inch touchscreen, Apple CarPlay, Android Auto, and the car’s comfortable, quiet character. It makes sense if you want the least expensive way into the model, but it is also the trim where the feature gap versus the higher versions is most obvious.
• 300 Touring L: This is the best-value choice for most shoppers because it adds a more upscale feel with Nappa leather and more available comfort and safety equipment. If you want the 300’s traditional luxury-sedan personality without jumping to the most expensive version, this is the trim to target.
• 300S: This is the most distinctive and best-equipped version, with 20-inch wheels, perforated inserts, accent stitching, and the option of the 5.7-liter V8. It suits you best if you want the strongest performance and the most premium presentation in the lineup.

Blind-spot monitoring and rear cross-traffic alert are only available on the Touring L or 300S, and the SafetyTec Plus Group is where you get the most advanced driver-assistance features.

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

This is a moderate market for selective buyers, so it makes sense to shop carefully and compare listings.

• Deal availability: 32.0% of listings are priced as good or great deals.
• Inventory: There are 491 listings available.
• Price trend: Prices have softened 7.20% compared with last year.
• Clean inventory: 62.1% of listings are accident-free.

If you find a listing below $19,627, 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 $19,661 sits slightly below last year's $21,186.

That decline suggests the market has softened, which can work against a future seller if you buy at the wrong price. On the other hand, the lower entry cost may help you avoid overpaying up front, which matters when you are thinking about eventual resale.

Because the 300 has a distinctive formula and a loyal audience, well-kept examples should still attract interest from buyers who want a traditional full-size sedan. If you buy a clean, well-equipped car and keep it in good condition, you improve your odds of holding value better than a neglected example.

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 scores in most IIHS crash tests, but it also receives a Marginal score in the small overlap tests and a Poor rating for headlights. It earns four-star overall ratings from NHTSA, with four-star driver and passenger side crash test ratings and a four-star rollover rating, plus a five-star rating in NHTSA's combined side barrier and side pole crash test.

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

All 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, 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.

The main safety caveat is that some of the more desirable features are not standard, so you need to check the exact trim and package content carefully.

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:

• 32.0% of listings are priced as good or great deals.
• At 62.1% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.
• Price trend: Prices have softened 7.20% compared with last year.
• Owners rate it 4.6/5 — a strong satisfaction signal.
• The 2021 model keeps the 300’s traditional rear-wheel-drive luxury-sedan formula, with available all-wheel drive and a 5.7-liter Hemi V8.

The bottom line: If you want the 300’s classic full-size sedan character, the 2021 is a sensible year to target because pricing has eased and the model still delivers the comfort, quiet cabin, and easy-to-use tech that define it. If you are especially price-sensitive, you can also compare nearby years, but the 2021 remains a strong pick for shoppers who value character and comfort over the newest features.

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 has the slight edge on overall score and brings more powertrain variety and a more performance-oriented personality. The 300 counters with a quieter, more comfort-focused cabin and easier technology, which may matter more if you want a relaxed daily driver.

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.