Used 2019 Chrysler 300 for Sale nearMilwaukee, WI
Shop with transparent pricing.
Only show listings that include dealer fees- Year:
- 2018
- Make:
- Chrysler
- Model:
- 300
- Body type:
- Sedan
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 300 hp 3.6L V6
- Exterior color:
- Gray
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 79,336
- Stock #:
- 149415
- VIN:
- 2C3CCAGG6JH149415

-$998

Sponsored by Lifetime Auto Sales
2018 Chrysler 300
S AWD
79,336 mi
$17,776
$16,778
- Year:
- 2020
- Make:
- Chrysler
- Model:
- 300
- Body type:
- Sedan
- Doors:
- 4 doors
- Drivetrain:
- Rear-Wheel Drive
- Engine:
- 300 hp 3.6L V6
- Exterior color:
- White
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 66,062
- Stock #:
- 233521
- VIN:
- 2C3CCABG6LH233521

2020 Chrysler 300
S RWD
66,062 mi
$19,512
- Year:
- 2018
- Make:
- Chrysler
- Model:
- 300
- Body type:
- Sedan
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 300 hp 3.6L V6
- Exterior color:
- Gray
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 79,336
- Stock #:
- 149415
- VIN:
- 2C3CCAGG6JH149415

-$998
2018 Chrysler 300
S AWD
79,336 mi
$17,776
$16,778
- Year:
- 2018
- Make:
- Chrysler
- Model:
- 300
- Body type:
- Sedan
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 300 hp 3.6L V6
- Exterior color:
- Gloss Black
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 94,522
- Stock #:
- J250747
- VIN:
- 2C3CCAGGXJH250747

2018 Chrysler 300
S AWD
94,522 mi
$18,408
- Year:
- 2018
- Make:
- Chrysler
- Model:
- 300
- Body type:
- Sedan
- Doors:
- 4 doors
- Drivetrain:
- Rear-Wheel Drive
- Engine:
- 292 hp 3.6L V6
- Exterior color:
- Black
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 95,830
- Stock #:
- 137687
- VIN:
- 2C3CCAAG0JH137687

2018 Chrysler 300
Touring L RWD
95,830 mi
$14,676
- Year:
- 2019
- Make:
- Chrysler
- Model:
- 300
- Body type:
- Sedan
- Doors:
- 4 doors
- Drivetrain:
- Rear-Wheel Drive
- Engine:
- 300 hp 3.6L V6
- Exterior color:
- Gray
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 68,569
- Stock #:
- 22358
- VIN:
- 2C3CCABG8KH537934

-$1,428
2019 Chrysler 300
S RWD
68,569 mi
$20,924
$19,995
- Year:
- 2018
- Make:
- Chrysler
- Model:
- 300
- Body type:
- Sedan
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 292 hp 3.6L V6
- Exterior color:
- Black
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Brown (TAN)
- Transmission:
- Automatic
- Mileage:
- 55,745
- Stock #:
- 231625
- VIN:
- 2C3CCAKG1JH231625

2018 Chrysler 300
Limited AWD
55,745 mi
$17,557
- Year:
- 2018
- Make:
- Chrysler
- Model:
- 300
- Body type:
- Sedan
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 300 hp 3.6L V6
- Exterior color:
- Black
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 93,253
- Stock #:
- 141372
- VIN:
- 2C3CCAGG7JH141372

2018 Chrysler 300
S AWD
93,253 mi
$17,127
- Year:
- 2018
- Make:
- Chrysler
- Model:
- 300
- Body type:
- Sedan
- Doors:
- 4 doors
- Drivetrain:
- Rear-Wheel Drive
- Engine:
- 300 hp 3.6L V6
- Exterior color:
- Silver
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 107,975
- Stock #:
- 214500
- VIN:
- 2C3CCABG6JH214500

2018 Chrysler 300
S RWD
107,975 mi
$14,357
- Year:
- 2018
- Make:
- Chrysler
- Model:
- 300
- Body type:
- Sedan
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 300 hp 3.6L V6
- Exterior color:
- Red (BURGUNDY)
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- 8-Speed Automatic
- Mileage:
- 120,342
- Stock #:
- 1587
- VIN:
- 2C3CCAGG0JH160636

2018 Chrysler 300
S AWD
120,342 mi
$14,542
- Year:
- 2018
- Make:
- Chrysler
- Model:
- 300
- Body type:
- Sedan
- Doors:
- 4 doors
- Drivetrain:
- Rear-Wheel Drive
- Engine:
- 300 hp 3.6L V6
- Exterior color:
- Black
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 96,061
- Stock #:
- 1505
- VIN:
- 2C3CCABG7JH121159

2018 Chrysler 300
S RWD
96,061 mi
$18,885
- Year:
- 2019
- Make:
- Chrysler
- Model:
- 300
- Body type:
- Sedan
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 292 hp 3.6L V6
- Exterior color:
- Black
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 115,694
- Stock #:
- AB16890
- VIN:
- 2C3CCAKGXKH610866

2019 Chrysler 300
Limited AWD
115,694 mi
$14,255
- Year:
- 2019
- Make:
- Chrysler
- Model:
- 300
- Body type:
- Sedan
- Doors:
- 4 doors
- Drivetrain:
- Rear-Wheel Drive
- Engine:
- 292 hp 3.6L V6
- Exterior color:
- Red (Burgundy)
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 99,500
- Stock #:
- 613563
- VIN:
- 2C3CCAAG5KH613563

2019 Chrysler 300
Touring RWD
99,500 mi
$16,453
CarGurus Analysis:
2019 Chrysler 300
With 61 currently listed for sale near Milwaukee, WI and an average price of $20,924.00, 21.3% of 2019 Chrysler 300s for sale on CarGurus are rated as good or great deals.
Favorably reviewed: Owners rated the 2019 Chrysler 300 4.62 / 5 stars.
70.5% of 2019 Chrysler 300 models on CarGurus are accident free.
- Year:
- 2018
- Make:
- Chrysler
- Model:
- 300
- Body type:
- Sedan
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 292 hp 3.6L V6
- Exterior color:
- Black
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 71,757
- Stock #:
- 324863
- VIN:
- 2C3CCARG3JH324863

2018 Chrysler 300
Touring AWD
71,757 mi
$18,486
- Year:
- 2019
- Make:
- Chrysler
- Model:
- 300
- Body type:
- Sedan
- Doors:
- 4 doors
- Drivetrain:
- Rear-Wheel Drive
- Engine:
- 292 hp 3.6L V6
- Exterior color:
- Gray (Ceramic Grey Clearcoat)
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 78,378
- Stock #:
- T568949
- VIN:
- 2C3CCAAG9KH568949

2019 Chrysler 300
Touring RWD
78,378 mi
$20,771
- Year:
- 2020
- Make:
- Chrysler
- Model:
- 300
- Body type:
- Sedan
- Doors:
- 4 doors
- Drivetrain:
- Rear-Wheel Drive
- Engine:
- 292 hp 3.6L V6
- Exterior color:
- Gloss Black
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 103,380
- Stock #:
- S131551
- VIN:
- 2C3CCAAG7LH131551

2020 Chrysler 300
Touring RWD
103,380 mi
$15,845
- Year:
- 2019
- Make:
- Chrysler
- Model:
- 300
- Body type:
- Sedan
- Doors:
- 4 doors
- Drivetrain:
- Rear-Wheel Drive
- Engine:
- 292 hp 3.6L V6
- Exterior color:
- White
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Transmission:
- 8-Speed Automatic
- Mileage:
- 94,946
- Stock #:
- 2836
- VIN:
- 2C3CCAEG3KH697473

2019 Chrysler 300
Limited RWD
94,946 mi
$14,830
- Year:
- 2019
- Make:
- Chrysler
- Model:
- 300
- Body type:
- Sedan
- Doors:
- 4 doors
- Drivetrain:
- Rear-Wheel Drive
- Engine:
- 292 hp 3.6L V6
- Exterior color:
- Gloss Black
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 91,800
- Stock #:
- 740641
- VIN:
- 2C3CCAAG9KH740641

2019 Chrysler 300
Touring RWD
91,800 mi
$15,523
- Year:
- 2019
- Make:
- Chrysler
- Model:
- 300
- Body type:
- Sedan
- Doors:
- 4 doors
- Drivetrain:
- Rear-Wheel Drive
- Engine:
- 292 hp 3.6L V6
- Exterior color:
- Black
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Brown (Beige)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 165,131
- Stock #:
- TR42096
- VIN:
- 2C3CCAAG9KH555893

2019 Chrysler 300
Touring RWD
165,131 mi
$10,616
- Year:
- 2019
- Make:
- Chrysler
- Model:
- 300
- Body type:
- Sedan
- Doors:
- 4 doors
- Drivetrain:
- Rear-Wheel Drive
- Engine:
- 292 hp 3.6L V6
- Exterior color:
- Black
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 66,137
- Stock #:
- 22391
- VIN:
- 2C3CCAAG5KH565000

2019 Chrysler 300
Touring RWD
66,137 mi
$18,995
- Year:
- 2018
- Make:
- Chrysler
- Model:
- 300
- Body type:
- Sedan
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 292 hp 3.6L V6
- Exterior color:
- Black
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 146,221
- Stock #:
- JYC-302283
- VIN:
- 2C3CCAKG4JH302283

2018 Chrysler 300
Limited AWD
146,221 mi
$10,754
- Year:
- 2019
- Make:
- Chrysler
- Model:
- 300
- Body type:
- Sedan
- Doors:
- 4 doors
- Drivetrain:
- Rear-Wheel Drive
- Engine:
- 292 hp 3.6L V6
- Exterior color:
- Gray (Granite Crystal Metallic Clearcoat)
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 70,323
- Stock #:
- 25050
- VIN:
- 2C3CCAAG0KH728944

2019 Chrysler 300
Touring RWD
70,323 mi
$19,118
- Year:
- 2018
- Make:
- Chrysler
- Model:
- 300
- Body type:
- Sedan
- Doors:
- 4 doors
- Drivetrain:
- Rear-Wheel Drive
- Engine:
- 292 hp 3.6L V6
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Transmission:
- 8-Speed Automatic
- Mileage:
- 101,074
- Stock #:
- 301540
- VIN:
- 2C3CCAEGXJH301540

2018 Chrysler 300
Limited RWD
101,074 mi
$17,053
CarGurus Analysis: 2019 Chrysler 300

Summary
With 61 currently listed for sale near Milwaukee, WI and an average price of $20,924.00, 21.3% of 2019 Chrysler 300s for sale on CarGurus are rated as good or great deals.
Favorably reviewed: Owners rated the 2019 Chrysler 300 4.62 / 5 stars.
70.5% of 2019 Chrysler 300 models on CarGurus are accident free.
Why it stands out
The 2019 Chrysler 300 stands out as a big, rear-wheel-drive American sedan that still leans into classic full-size-car appeal. By this point in its run, the 300 had already settled into a familiar formula: roomy proportions, a comfortable ride, and a choice of durable V6 and V8 powertrains. It also remained one of the few cars in its class with genuine retro presence, which helps explain why it continued to attract buyers looking for something more distinctive than a typical midsize sedan.
For 2019, the 300 was essentially frozen in time after 2019, so its appeal came less from constant reinvention and more from the strength of its established package. The UConnect system had already gained Apple CarPlay and Android Auto in 2017, and the car’s available safety and infotainment features were part of what later models offered. Buyers who wanted a large sedan with a smooth ride and strong engine choices could still find plenty to like, especially since owners often praise its comfort, power, and spacious cabin.
The tradeoff is that the 2019 Chrysler 300 could feel dated next to newer rivals, and it was never the most performance-focused choice in its family. Its size also meant a big appetite for fuel. Even so, for shoppers who value space, comfort, and traditional sedan character, the 2019 300 remained a compelling used-car option.
Other model years to consider
- Average price: $17,387.00
- Good/great deal percentage: 19.7%
- User rating: 4.75 / 5
- Total listings: 71
- Average price: $20,992.00
- Good/great deal percentage: 23.2%
- User rating: 4.78 / 5
- Total listings: 56
- Average price: $23,985.00
- Good/great deal percentage: 26.2%
- User rating: 4.6 / 5
- Total listings: 42
This analysis is based on CarGurus' proprietary market data from August 18, 2026, CarGurus experts' opinions, and generative AI.
4.7 Overall rating
Filter by rating
shane h
Reviewed a 2019 Chrysler 300 on Jan 5, 2021
Perfect, it’s more than i expected. Amazing car, Drives absolutely smooth. Love it!
Ramon F
Reviewed a 2019 Chrysler 300 on Mar 5, 2021
I love the Chrysler 300 that I recently purchased. The car rides really smooth, I love the space inside of the car and I really love the upgraded sound system. The big LCD screen is a major plus.
Rudolph R
Reviewed a 2019 Chrysler 300 on Sep 8, 2020
It is a lot of car for the money. The Ltd version is a charm to drive, quiet yet powerful. With the right options, I feel it is very safe.
Anonymous
Reviewed a 2019 Chrysler 300 on Feb 13, 2024
Was looking for a comfortable ride, with plenty of room and this car has just that. Like the look inside and out.
2019 Chrysler 300 Trims
| Trim type | MSRP |
|---|---|
| C RWD | $41,695 |
| Touring AWD | $31,720 |
| Touring L RWD | $32,865 |
| Limited AWD | $40,745 |
| S AWD | $38,895 |
| Limited RWD | $38,245 |
| S RWD | $36,395 |
| Touring RWD | $29,220 |
2019 Chrysler 300 Price Trends
CarGurus tracks the prices of millions of used car listings every year. See how the average price of 2019 Chrysler 300 prices has changed over time.
See more price trends2019 Chrysler 300 Pricing Analysis: Milwaukee, WI Market Report
Pricing by Nearby Locations
Market Area: Milwaukee, WI
Key Insights
- Lowest Prices in Fond du Lac: The market in Fond du Lac, WI ($11,995) offers the most affordable options, likely due to higher inventory and lower demand.
- Highest Prices in Kenosha: Conversely, Kenosha, WI ($20,305) has the highest average price, indicating a potential scarcity of inventory or higher demand for the model.
- Inventory Variation: Cities like Chicago (72 listings) and Aurora (72 listings) show a strong inventory presence, which correlates with more competitive pricing around $15,493 to $15,253.
City-Level Pricing
| City | Total Listings | Avg Price |
|---|---|---|
| Kenosha, WI | 69 | $20,305 |
| Palatine, IL | 71 | $16,792 |
| Janesville, WI | 65 | $16,600 |
| Rockford, IL | 54 | $16,600 |
| Chicago, IL | 72 | $15,493 |
| Aurora, IL | 72 | $15,253 |
| Appleton, WI | 49 | $11,995 |
| Fond du Lac, WI | 61 | $11,995 |
Pricing by Trim Packages
Key Insights
- RWD Trims Dominate Listings: The Touring RWD (33 listings) is the most common trim, indicating strong demand for this configuration.
- Price Range Across Trims: The C RWD ($41,695 MSRP) is the highest priced trim, reflecting its premium features and V8 engine, while the Touring L AWD ($35,365 MSRP) offers a more affordable AWD option.
- Feature-Rich Options: Trims like the Limited RWD and S RWD provide a balance of luxury and performance, appealing to a broader range of buyers.
Trim-Level Details
| Trim | Listings | MSRP | Drivetrain | Engine |
|---|---|---|---|---|
| Touring RWD | 33 | $29,220 | RWD | 3.6L 292 hp V6 |
| Limited RWD | 23 | $38,245 | RWD | 3.6L 292 hp V6 |
| S RWD | 18 | $36,395 | RWD | 3.6L 300 hp V6 |
| C RWD | 15 | $41,695 | RWD | 5.7L 363 hp V8 |
| S AWD | 24 | $38,895 | AWD | 3.6L 300 hp V6 |
| Limited AWD | 18 | $40,745 | AWD | 3.6L 292 hp V6 |
| Touring L RWD | 12 | $32,865 | RWD | 3.6L 292 hp V6 |
| Touring L AWD | 7 | $35,365 | AWD | 3.6L 292 hp V6 |
Pricing Analysis by Model Year
Key Insights
- Significant Depreciation for Older Models: The 2016 Chrysler 300 shows a steep decline, priced at $9,495, which is ~70.5% below MSRP.
- Best Value in Recent Models: The 2021 model is priced at $23,985, reflecting a depreciation of only ~24.5%, making it a strong value for buyers seeking newer vehicles.
- Newer Models Retain Value: The 2023 model is currently priced at $31,733, which is about -3.3% below its MSRP, indicating strong demand for the latest model year.
Model Year Pricing
| Model Year | Original MSRP | Avg Price | Price vs MSRP |
|---|---|---|---|
| 2023 Chrysler 300 | $34,295 | $31,733 | -3.3% |
| 2021 Chrysler 300 | $31,875 | $23,985 | -24.5% |
| 2020 Chrysler 300 | $30,040 | $20,992 | -30.1% |
| 2018 Chrysler 300 | $28,995 | $17,387 | -40.1% |
| 2016 Chrysler 300 | $32,260 | $9,495 | -70.5% |
| 2015 Chrysler 300 | $31,695 | $9,225 | -70.9% |
| 2013 Chrysler 300 | $30,345 | $4,999 | -84.5% |
| 2012 Chrysler 300 | $27,470 | $3,500 | -87.3% |
| 2011 Chrysler 300 | $27,170 | $5,999 | -77.9% |
These recommendations are based on CarGurus' proprietary market data from August 20, 2026, CarGurus experts' opinions, and generative AI.
How much does the 2019 Chrysler 300 cost?
| Metric | Value |
|---|---|
| Current Average Price | $16,309 |
| Year-Round Low | $16,102.28 |
| Year-Round High | $17,530.78 |
| Average Price a Year Ago | $17,532 |
| Change vs. Last Year | −6.98% |
Prices have softened 6.98% compared to this time last year, making it a favorable time to shop this model year.
There are 699 listings available, which suggests you should have some room to compare prices and conditions.
If you find a listing below $16,102.28, that's toward the low end of the year-round range and worth acting on quickly.
Is the 2019 Chrysler 300 a good car?
Yes — the 2019 Chrysler 300 earns a 4.62/5 user rating, which points to strong owner satisfaction. Owners consistently praise its smooth ride, powerful engines, and spacious interior, and many also see it as a good value for the price. For you, that makes it a strong fit if you want a large sedan with comfort and traditional full-size character rather than a smaller, more modern-feeling alternative. With 27.6% of listings marked as good or great deals, there are still some attractive opportunities if you shop carefully.
Is the 2019 Chrysler 300 reliable?
Owners rate it 4.62/5, a strong signal of long-term satisfaction.
The owner feedback also emphasizes a dependable-feeling driving experience, with praise for the smooth ride and powerful engines that help the car feel easy to live with over time. That kind of feedback matters if you want a used sedan you can count on for regular driving without feeling like you’re constantly compromising on comfort.
For used buyers, the main long-term ownership risk is less about the core appeal and more about finding a well-kept example that has been maintained properly.
What should I look for when buying a used 2019 Chrysler 300?
At 56.4% 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 past damage. After that, prioritize a thorough pre-purchase inspection, especially if the listing price looks unusually attractive.
Focus on overall condition, maintenance records, and signs that the car has been cared for consistently. Because this model is valued for comfort and space, you’ll want to make sure the cabin, ride quality, and major mechanical systems still reflect that promise.
Is now a good time to buy a used 2019 Chrysler 300?
This looks like a moderate, selective buyer’s market, so you can shop with some leverage if you’re patient and compare listings closely.
- Deal availability: 27.6% of listings are priced as good or great deals.
- Inventory: There are 699 listings available.
- Price trend: Prices have softened 6.98% compared with last year.
- Clean inventory: 56.4% of listings are accident-free.
If you find a listing below $16,102.28, that's toward the low end of the year-round range and worth acting on quickly.
What is the 2019 Chrysler 300's resale value?
The current average of $16,309 sits slightly below last year's $17,532.
That softer pricing suggests the market has already adjusted downward, which can help you as a buyer today but may also limit upside if you plan to resell soon. If you buy at a strong price and keep the car in good condition, you’ll be better positioned to protect value later.
Vehicles with strong owner satisfaction ratings, like this model year's 4.62/5, tend to retain buyer demand, which supports resale value over time.
Should I buy a 2019 Chrysler 300 or consider a different year?
If you're weighing the 2019 against nearby model years, here's how to think about it:
Choose the 2019 if:
- 27.6% of listings are priced as good or great deals.
- At 56.4% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.
- Price trend: Prices have softened 6.98% compared with last year.
- Owners rate it 4.62/5 — a strong satisfaction signal.
The bottom line:
If you want a large, comfortable sedan with strong owner approval and you’re focused on value, the 2019 Chrysler 300 is a sensible choice. If you’re especially price-sensitive, you may want to compare it closely with nearby model years and target the cleanest, best-priced example rather than buying the first one you see.
These recommendations are based on CarGurus' proprietary market data from August 21, 2026, CarGurus experts' opinions, and generative AI.
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Chrysler 300 Buying Guide: Cost, Reliability, and the Best Years to Buy
Discover the ultimate buying guide for purchasing a used Chrysler 300, covering every generation since the modern 300 debuted in 2005. Whether you're a first-time buyer or a Chrysler enthusiast, this comprehensive overview will help you research your next pre-owned Chrysler 300.

Who Makes Chrysler Cars?
Chrysler is a long-running American legacy, founded in 1925. Though it was once a premier American luxury brand, things are quieter there now, as it only sells three variants of a minivan. It is a division of Stellantis, which is also the parent company of Jeep, Dodge, Ram, and others.