Used 2020 Chrysler 300 for Sale near Madison, WI
51 results
CarGurus Analysis:
2020 Chrysler 300
With 596 currently listed for sale and an average price of $18,669.00, 28.7% of 2020 Chrysler 300s for sale on CarGurus are rated as good or great deals.
Favorably reviewed: Owners rated the 2020 Chrysler 300 4.78 / 5 stars.
59.2% of 2020 Chrysler 300 models on CarGurus are accident free.
CarGurus Analysis: 2020 Chrysler 300

Summary
With 596 currently listed for sale and an average price of $18,669.00, 28.7% of 2020 Chrysler 300s for sale on CarGurus are rated as good or great deals.
Favorably reviewed: Owners rated the 2020 Chrysler 300 4.78 / 5 stars.
59.2% of 2020 Chrysler 300 models on CarGurus are accident free.
Why it stands out
The 2020 Chrysler 300 offers a compelling blend of classic American styling and modern performance, making it a notable entry in the full-size sedan market. Known for its spacious interior and comfortable ride, this sedan features powerful V6 and V8 engine options, appealing to buyers who seek both luxury and capability. The 300 manages to maintain a classically appealing design while integrating functional tech upgrades, including advanced infotainment systems. However, some users have raised concerns regarding its safety features and cramped foot space for taller individuals. Overall, the combination of a smooth ride, an abundance of power, and an attractive price point makes the 2020 Chrysler 300 a solid choice for those in the market for a used full-size sedan.
Other model years to consider
- Average price: $14,487.00
- Good/great deal percentage: 26.0%
- User rating: 5 / 5
- Total listings: 647
- Average price: $15,300.00
- Good/great deal percentage: 29.4%
- User rating: 4.75 / 5
- Total listings: 766
- Average price: $24,251.00
- Good/great deal percentage: 27.3%
- User rating: 4.9 / 5
- Total listings: 697
This analysis is based on CarGurus' proprietary market data from May 4, 2026, CarGurus experts' opinions, and generative AI.
Relevant articles

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.
4.8 Overall rating
Filter by rating
Philip D
Reviewed a 2020 Chrysler 300 on Mar 12, 2024
Nice features. The car is missing a warranty and a new tire.
Glen S
Reviewed a 2020 Chrysler 300 on Jul 31, 2023
It was a lovely car. Quiet and smooth riding. There were a few maintenance issues but nothing that couldnt be fixed.
MICHAEL M
Reviewed a 2020 Chrysler 300 on Nov 19, 2020
Best sedan in its category. Built well and updated but not drastically changed over time. Lot of room inside and solid construction. Very quiet ride and good power. Gets 20 MPG in city and about 28 MPG on highway. I love mine and used low mileage vehicle are a bargain.
Christopher T
Reviewed a 2020 Chrysler 300 on Jun 9, 2021
It’s a Quality Automobile which is Durable, Spacious, Reliable, with Great Value. My next Car will be a 2019 or 2020 Chrysler 300 Limited.
2020 Chrysler 300 Trims
| Trim type | MSRP |
|---|---|
| Touring L AWD | $36,065 |
| Touring L RWD | $33,315 |
| S AWD | $39,445 |
| Touring AWD | $32,790 |
| Limited AWD | $41,345 |
| Limited RWD | $38,595 |
| S RWD | $36,995 |
| Touring RWD | $30,040 |
2020 Chrysler 300 Price Trends
CarGurus tracks the prices of millions of used car listings every year. See how the average price of 2020 Chrysler 300 prices has changed over time.
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