Used 2019 Toyota Highlander for Sale near Chicago, IL

## Summary - With 2,357 currently listed for sale on CarGurus and an **average price of $23,246.00**, 36.3% of 2019 Toyota Highlanders for sale on CarGurus are rated as good or great deals. - **Favorably reviewed:** Owners rated the 2019 Toyota Highlander 4.57 / 5 stars. - **64.9% of 2019 Highlander models on CarGurus are accident free**. - The 2019 Toyota Highlander is appreciated for its comfort, spaciousness, and reliability, with notable safety features and solid engine performance. ## Why it stands out The 2019 Toyota Highlander remains a strong contender in the midsize SUV segment, offering a blend of comfort and practicality that appeals to families. This model is particularly known for its spacious interior, providing ample room for passengers and cargo alike, which is a significant advantage for those needing a family vehicle. Customers have praised its reliable performance, with a user-friendly engine that delivers a smooth drive. While it isn't characterized by sporty handling, the Highlander excels in comfort, making it a favorite for everyday use. However, potential buyers should take note that some reviews indicate a desire for more rear seat space and a higher price point relative to competitors, which could influence purchasing decisions. ## Other model years to consider - **[2022 Toyota Highlander](https://www.cargurus.com/Cars/l-Used-2022-Toyota-Highlander-c31996)** - Average price: $32,510.00 - Good/great deal percentage: 32.3% - User rating: 4.58 / 5 - Total listings: 4,192 - **[2021 Toyota Highlander](https://www.cargurus.com/Cars/l-Used-2021-Toyota-Highlander-c30910)** - Average price: $29,334.00 - Good/great deal percentage: 33.5% - User rating: 4.82 / 5 - Total listings: 2,772 - **[2015 Toyota Highlander](https://www.cargurus.com/Cars/l-Used-2015-Toyota-Highlander-c24608)** - Average price: $16,511.00 - Good/great deal percentage: 36.8% - User rating: 4.76 / 5 - Total listings: 1,203 --- This analysis is based on CarGurus' proprietary market data from March 2, 2026, CarGurus experts' opinions, and generative AI.