Used 2021 Chrysler 300 for Sale nearChicago, IL

How much does the 2021 Chrysler 300 cost?

Prices have softened 9.88% compared to this time last year, making it a favorable time to shop this model year.

There are 511 listings available, which gives you a meaningful 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 7.67/10 expert rating. The standout strength is Technology at 9/10.

Owners repeatedly praise the luxurious look, smooth ride, strong handling, acceleration, and comfort. In practical terms, that lines up with a sedan that feels upscale, quiet, and easy to live with.

The main trade-off is that it can feel like poor value for money, and the design is aging. Even so, the 300 still makes sense if you want a comfortable, rear-wheel-drive luxury sedan with available all-wheel drive or V8 power.

With 29.7% of listings marked as good or great deals, you have 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 a generally trouble-free ownership experience. That kind of feedback matters when you’re shopping used, because it suggests the car can be counted on for regular driving rather than just short-term appeal.

The expert evaluation also describes it as quiet, capable, and comfortable on the road, which supports the idea that it remains a solid long-term cruiser. If you’re buying used, the bigger risk is less about the basic drivetrain concept and more about finding a well-kept example with the right equipment and condition.

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

At 66.7% 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-mileage car or one with optional safety equipment. Focus on condition, maintenance records, and whether the features you want are actually present on the trim you’re looking at.

Key things to evaluate:

• Trim level: The base 300 Touring uses 17-inch silver alloys, cloth upholstery, and an eight-way power driver’s seat, while the 300 Touring L adds Nappa leather upholstery and 18-inch polished alloys. The 300S brings standard 20-inch Black Noise wheels, perforated inserts, accent stitching, and a more upscale feel, so the lower trim is the one most likely to feel stripped down.
• Powertrain: The 3.6-liter Pentastar V6 makes 292 horsepower and 260 pound-feet of torque in the Touring and Touring L, while the 300S gets 300 horsepower and 264 pound-feet. The 300S also offers a 5.7-liter V8 with 363 horsepower and 394 pound-feet, and all versions use an eight-speed automatic.
• 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 only available on 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 easy to use, and 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. AWD 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 value play if you want the Chrysler 300 experience at the lowest entry point. You still get the 8.4-inch touchscreen, Apple CarPlay, Android Auto, and the core rear-wheel-drive luxury-sedan character, but it’s the trim most likely to feel basic on wheels and upholstery.
• 300 Touring L: This is the best-value trim for most shoppers because it adds Nappa leather upholstery and a more upscale cabin without jumping all the way to the V8-focused 300S. If you want the strongest mix of comfort and price, this is the one to target.
• 300S: Choose this if you want the sportier look and feel, plus the option of the 5.7-liter V8. It adds standard 20-inch wheels, perforated inserts, accent stitching, and paddle shifters, but it’s the least budget-friendly route.

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

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

This is a moderate market, so you can shop selectively without expecting every listing to be a bargain.

• Deal availability: 29.7% of listings are priced as good or great deals.
• Inventory: There are 511 listings available.
• Price trend: Prices have softened 9.88% compared with last year.
• Clean inventory: 66.7% of listings are accident-free.

If you find a listing below $20,205, 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 $20,206 sits slightly below last year's $22,421.

That decline suggests the market has already adjusted downward, which can help you as a buyer but may limit upside if you plan to resell soon. For a future seller, the key takeaway is that this model year is holding value more through niche appeal than broad-market demand.

Because the 300 still offers a distinctive rear-drive luxury-sedan formula, well-kept examples should remain easier to move than more ordinary large sedans. Strong equipment, clean history, and desirable trims should matter more than mileage alone when you eventually 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 received top "Good" scores in all Insurance Institute for Highway Safety (IIHS) crash tests except the small overlap tests, where it received a "Marginal" score. It also received a "Poor" rating for headlights. Over at the National Highway Traffic Safety Administration (NHTSA), the 300 received a four-star overall crash test rating, with four-star driver and passenger side crash test ratings, and a four-star rollover rating. On the plus side, it received a five-star rating for NHTSA's combined side barrier and side pole crash test.

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

All Chrysler 300s offer active head restraints, an arsenal of airbags, traction and stability control with brake assist, rain brake support, ready alert braking, and hill start assist.

Advanced safety equipment is not evenly spread across the lineup. Blind-spot monitoring and rear cross-traffic alert are only available on the Touring L or 300S trims, 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 Marginal small-overlap result and Poor headlight rating are the main caveats to keep in mind if safety is a top priority.

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:

• 29.7% of listings are priced as good or great deals.
• At 66.7% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.
• Price trend: Prices have softened 9.88% compared with last year.
• Owners rate it 4.6/5 — a strong satisfaction signal.
• You want a rare, rear-wheel-drive luxury sedan with available all-wheel drive or a 5.7-liter Hemi V8.

The bottom line: The 2021 Chrysler 300 makes the most sense if you want a distinctive full-size sedan with comfort, strong road manners, and a traditional luxury feel. If you’re price-sensitive, the current market gives you room to shop carefully, but you should prioritize condition and equipment because the best examples will be the ones that age most gracefully.

These recommendations are based on CarGurus' proprietary market data from September 22, 2026, CarGurus experts' opinions, and generative AI.