Used Jeep Cherokee for Sale near Chicago, IL

Summary

• With 4,947 currently listed for sale on CarGurus and an average price of $15,815.40, 33.2% of 2019 Jeep Cherokees for sale on CarGurus are rated as good or great deals.
• Favorably reviewed: Owners rated the 2019 Jeep Cherokee 4.5 / 5 stars and CarGurus experts gave it an 8 / 10.
• 68% of 2019 Cherokee models on CarGurus are accident free.
• The 2019 Jeep Cherokee excelled with its off-road capability, featuring advanced four-wheel-drive systems for tackling diverse terrains with confidence.

Why it stands out

The Jeep Cherokee stands out in the compact crossover market due to its exceptional off-road capabilities, particularly in the Trailhawk trim, which rivals even the legendary Jeep Wrangler. Its advanced 4-wheel-drive and terrain-management systems offer both rugged performance and enhanced on-road comfort, making it a versatile option for those who seek adventure without sacrificing daily usability. Additionally, with a more affordable price point than the Grand Cherokee, it presents a compelling choice for Jeep enthusiasts looking for an accessible SUV that doesn't compromise on capability.

Other model years to consider

The 2020 Jeep Cherokee stands out as a great option with a competitive average price of $17,818.45 and an impressive user rating of 4.6 out of 5, alongside a solid 34% of listings categorized as good or great deals. The 2018 model also offers significant value at an average price of $13,934.89 and a user rating of 4.4 out of 5, making it another moderately suitable alternative with a similar proportion of good deals available. Additionally, the 2015 model presents an appealing option for budget-conscious buyers, featuring an average price of just $10,008.02 and a respectable user rating of 4.5 out of 5, with about 32% classified as good or great deals.

Model years to approach with caution

In analyzing the Jeep Cherokee model years, several factors come into play. The 1998 and 2000 models stand out as the most suitable options, both receiving strong user ratings and typically commanding reasonable prices in the marketplace. On the other hand, while the 2014 model is available at a lower average price, it shows a decline in customer satisfaction, with many users rating it below previous generations. Overall, potential buyers should consider these aspects carefully to make an informed decision that aligns with their preferences for value and satisfaction.

These recommendations are based on CarGurus' proprietary market data from December 3, 2025, CarGurus experts' opinions, and generative AI.