Used Jeep Cherokee for Sale near Milwaukee, WI

Summary

• With 4,949 currently listed for sale on CarGurus and an average price of $15,711.60, 33.6% 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.
• 67.8% of 2019 Cherokee models on CarGurus are accident free.
• The 2019 Jeep Cherokee provided impressive off-road capability, with multiple four-wheel drive systems available for diverse terrain challenges.

Why it stands out

The Jeep Cherokee stands out in the compact SUV segment with its unmatched off-road capabilities, particularly in the Trailhawk trim, which is engineered to tackle rugged terrains alongside the legendary Jeep Wrangler. Its advanced 4-wheel-drive and terrain-management systems provide a competitive edge, making it an appealing choice for adventure seekers who desire both affordability and performance. Additionally, the Cherokee's recent redesign enhances its aesthetics and interior comfort, attracting buyers looking for a capable yet stylish SUV.

Other model years to consider

The 2022 Jeep Cherokee stands out as a highly viable option, featuring an average price of $24,149.72 and an impressive user rating of 4.8/5, alongside a significant proportion of good deals in the market at 35%. The 2021 model also presents a strong value proposition with a competitive price of $20,190.23 and a user satisfaction rating of 4.8/5, reflecting consistent performance and reliability among buyers. Additionally, the 2020 model offers an attractive balance with its lower price point of $17,744.56 and a solid user rating of 4.6/5, making it a well-rounded choice for those seeking both value and quality in their vehicle purchase.

Model years to approach with caution

When considering the Jeep Cherokee, buyers should carefully evaluate the 2017 and 2014 model years due to their pricing trends and user ratings. The average price for the 2017 model is relatively high at $12,225.22, yet a significant percentage of listings (68%) are categorized as not good or great deals, suggesting limited value for potential buyers. Similarly, while the 2014 model has a lower average price of $9,294.61, it also features a comparatively lower user rating of 3.8/5 and an even higher percentage (73%) of listings that are not considered good or great deals, indicating that buyers may find fewer appealing options within these years.

These recommendations are based on CarGurus' proprietary market data from December 9, 2025, CarGurus experts' opinions, and generative AI.