Used 2021 Jeep Cherokee for Sale near Chicago, IL

## Summary - With 241 currently listed for sale near Chicago, IL and an **average price of $18,243.00**, 33.6% of 2021 Jeep Cherokees for sale on CarGurus are rated as good or great deals. - **Favorably reviewed:** Owners rated the 2021 Jeep Cherokee 4.81 / 5 stars. - **90.9% of 2021 Cherokee models on CarGurus are accident free.** - The 2021 Jeep Cherokee features impressive technology, ease of use in its infotainment system, and notable off-road capabilities especially in the Trailhawk trim. ## Why it stands out The 2021 Jeep Cherokee stands out in the compact SUV segment for its balance of style, capability, and advanced features. Drivers appreciate its smooth ride quality and robust safety technologies, making it a competitive choice for those looking for both comfort and practicality. The Cherokee is particularly appealing for buyers seeking off-road capabilities, especially with the Trailhawk trim, which includes features like Jeep Active Drive Lock and Selec-Speed Crawl Control. Although some might find its cargo space somewhat lacking compared to rivals, the Cherokee compensates with tech-savvy interiors and a unique aesthetic that differentiates it from the crowded SUV market. Additionally, the generous user rating reflects overall satisfaction among owners, enhancing its appeal as a family-friendly option. ## Other model years to consider - **[2019 Jeep Cherokee](https://www.cargurus.com/Cars/l-Used-2019-Jeep-Cherokee-Chicago-c27481_L7510)** - Average price: $14,321.00 - Good/great deal percentage: 35.7% - User rating: 4.47 / 5 - Total listings: 345 - **[2018 Jeep Cherokee](https://www.cargurus.com/Cars/l-Used-2018-Jeep-Cherokee-Chicago-c27056_L7510)** - Average price: $13,077.00 - Good/great deal percentage: 31.8% - User rating: 4.39 / 5 - Total listings: 327 - **[2020 Jeep Cherokee](https://www.cargurus.com/Cars/l-Used-2020-Jeep-Cherokee-Chicago-c29396_L7510)** - Average price: $16,070.00 - Good/great deal percentage: 44.4% - User rating: 4.62 / 5 - Total listings: 187 This analysis is based on CarGurus' proprietary market data from March 24, 2026, CarGurus experts' opinions, and generative AI.