Used 2020 Chrysler 300 for Sale near Chicago, IL
62 results
CarGurus Analysis:
2020 Chrysler 300
With 68 currently listed for sale near Chicago, IL and an average price of $17,108.00, 26.5% of 2020 Chrysler 300s for sale on CarGurus are rated as good or great deals.
Favorably reviewed: Owners rated the 2020 Chrysler 300 4.56 / 5 stars.
75.0% of 2020 Chrysler 300 models on CarGurus are accident free.
The 2020 Chrysler 300 is noted for its spacious interior, strong engines, and smooth ride, making it a standout in the full-size sedan market.
CarGurus Analysis: 2020 Chrysler 300

Summary
With 68 currently listed for sale near Chicago, IL and an average price of $17,108.00, 26.5% of 2020 Chrysler 300s for sale on CarGurus are rated as good or great deals.
Favorably reviewed: Owners rated the 2020 Chrysler 300 4.56 / 5 stars.
75.0% of 2020 Chrysler 300 models on CarGurus are accident free.
The 2020 Chrysler 300 is noted for its spacious interior, strong engines, and smooth ride, making it a standout in the full-size sedan market.
Why it stands out
The 2020 Chrysler 300 is a compelling choice for buyers seeking a full-size sedan that blends classic American styling with modern comforts. Its well-built structure, smooth ride, and choice of powerful engines, including the robust 5.7-liter Hemi V8, contribute to its appeal. While the 300 delivers ample space for both passengers and cargo, it is often lauded for its affordability compared to competitors. However, some drivers have raised concerns about its safety features and cramped foot space for taller occupants. Overall, the Chrysler 300 manages to strike a balance between luxury and practicality, making it a desirable option for many sedan shoppers.
Other model years to consider
- Average price: $13,686.00
- Good/great deal percentage: 14.9%
- User rating: 4.6 / 5
- Total listings: 87
- Average price: $15,400.00
- Good/great deal percentage: 26.1%
- User rating: 4.58 / 5
- Total listings: 88
- Average price: $26,406.00
- Good/great deal percentage: 23.3%
- User rating: 4.93 / 5
- Total listings: 73
This analysis is based on CarGurus' proprietary market data from April 7, 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
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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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