Used 2020 Jeep Grand Cherokee for Sale near Chicago, IL

## Summary - With 252 currently listed for sale near Chicago, IL and an **average price of $23,360.00**, 37.7% 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 4.66 / 5 stars. - **100.0% of 2020 Grand Cherokee models on CarGurus are accident free**. - The 2020 Jeep Grand Cherokee boasts a stylish design with excellent off-road capabilities and provides an array of powerful engine options, including a highly praised V8. ## Why it stands out The 2020 Jeep Grand Cherokee is celebrated for its versatility as a midsize SUV, adept in both rugged terrains and luxurious settings alike. It showcases traditional Jeep styling with its iconic 7-slot grille and trapezoidal fenders, creating an attractive appearance suitable for various social settings. Notably, the Grand Cherokee offers numerous engine choices, including a formidable 707-horsepower supercharged V8 in the Trackhawk variant, making it a thrilling option for performance enthusiasts. Although praised for its off-road capabilities and luxurious features, some owners have expressed concerns over fuel efficiency and certain interior build quality aspects. Expert reviews indicate that its driving dynamics can be a mixed bag, often leading to a less comfortable ride on bumpy roads. However, the 2020 model's impressive technology, including the Uconnect system and various advanced safety features, helps maintain its position as a standout SUV. ## Other model years to consider - **[2022 Jeep Grand Cherokee](https://www.cargurus.com/Cars/l-Used-2022-Jeep-Grand-Cherokee-Chicago-c31991_L7510)** - Average price: $29,393.00 - Good/great deal percentage: 55.1% - User rating: 4.73 / 5 - Total listings: 283 - **[2015 Jeep Grand Cherokee](https://www.cargurus.com/Cars/l-Used-2015-Jeep-Grand-Cherokee-Chicago-c24473_L7510)** - Average price: $13,158.00 - Good/great deal percentage: 30.3% - User rating: 4.68 / 5 - Total listings: 277 - **[2016 Jeep Grand Cherokee](https://www.cargurus.com/Cars/l-Used-2016-Jeep-Grand-Cherokee-Chicago-c25592_L7510)** - Average price: $14,983.00 - Good/great deal percentage: 27.1% - User rating: 4.77 / 5 - Total listings: 329 This analysis is based on CarGurus' proprietary market data from March 24, 2026, CarGurus experts' opinions, and generative AI.