Used 2020 Jeep Grand Cherokee for Sale near Chicago, IL
250 results
CarGurus Analysis:
2020 Jeep Grand Cherokee
With 248 currently listed for sale near Chicago, IL and an average price of $23,315.00, 39.9% of 2020 Jeep Grand Cherokees for sale on CarGurus are rated as good or great deals.
Favorably reviewed: Owners rated the 2020 Jeep Grand Cherokee 4.58 / 5 stars.
100.0% of 2020 Grand Cherokee models on CarGurus are accident free.
The 2020 Jeep Grand Cherokee is known for its comfort, powerful engine options, and advanced safety features, making it a popular choice for both off-road adventures and daily driving.
CarGurus Analysis: 2020 Jeep Grand Cherokee
overall
Summary
With 248 currently listed for sale near Chicago, IL and an average price of $23,315.00, 39.9% of 2020 Jeep Grand Cherokees for sale on CarGurus are rated as good or great deals.
Favorably reviewed: Owners rated the 2020 Jeep Grand Cherokee 4.58 / 5 stars.
100.0% of 2020 Grand Cherokee models on CarGurus are accident free.
The 2020 Jeep Grand Cherokee is known for its comfort, powerful engine options, and advanced safety features, making it a popular choice for both off-road adventures and daily driving.
Why it stands out
The 2020 Jeep Grand Cherokee remains a compelling option in the midsize SUV segment, known for its stylish design and impressive off-road capabilities. With a variety of engine options including a robust V8 that delivers spirited performance, it caters to a wide range of buyers looking for power and versatility. The spacious interior offers seating for five and practical cargo space, although some may find the seating uncomfortable for longer trips. Notable features like the advanced Uconnect infotainment system and various safety technologies enhance its appeal. Moreover, the Grand Cherokee thrives in both urban settings and more rugged terrains, which is a rare combination in today’s SUV marketplace. However, prospective buyers should be aware of the trade-offs, including advanced safety features that are not standard and relatively high operating costs compared to more efficient rivals.
Other model years to consider
- Average price: $31,977.00
- Good/great deal percentage: 76.8%
- User rating: 5 / 5
- Total listings: 310
- Average price: $29,346.00
- Good/great deal percentage: 73.7%
- User rating: 4.86 / 5
- Total listings: 297
- Average price: $34,288.00
- Good/great deal percentage: 79.2%
- User rating: 5 / 5
- Total listings: 293
This analysis is based on CarGurus' proprietary market data from April 28, 2026, CarGurus experts' opinions, and generative AI.
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4.6 Overall rating
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Anonymous
Reviewed a 2020 Jeep Limited 4WD on Jul 30, 2025
I love all the features on this car. I think it was a great value. Its the JGC X, which has a little more options than regular. Love the slate blue color.
Samuel M
Reviewed a 2020 Jeep Grand Cherokee on Dec 19, 2025
2nd Jeep Cherokee we have bought and they are great vehicles and very reliable.
Jennifer V
Reviewed a 2020 Jeep Grand Cherokee on May 5, 2024
Vehicle spent time in rusty states. Rust on the hood latch. Rust spots on the rotors.
Tristan H
Reviewed a 2020 Jeep Grand Cherokee on Jan 10, 2025
Great car loads of features! Amazing platform plenty of power and capability.
2020 Jeep Grand Cherokee Trims
| Trim type | MSRP |
|---|---|
| High Altitude 4WD | $52,440 |
| Trailhawk 4WD | $45,155 |
| Limited RWD | $39,955 |
| Limited X 4WD | $47,050 |
| Overland 4WD | $49,695 |
| Laredo E 4WD | $36,000 |
| Altitude 4WD | $40,540 |
| Limited 4WD | $41,955 |
2020 Jeep Grand Cherokee Price Trends
CarGurus tracks the prices of millions of used car listings every year. See how the average price of 2020 Jeep Grand Cherokee prices has changed over time.
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