Used 2016 Toyota Highlander for Sale near Chicago, IL

## Summary - With 101 currently listed for sale near Chicago, IL and an **average price of $18,063.00**, 25.7% of 2016 Toyota Highlanders for sale on CarGurus are rated as good or great deals. - **Favorably reviewed:** Owners rated the 2016 Toyota Highlander 4.63 / 5 stars. - **76.2% of 2016 Highlander models on CarGurus are accident free**. - The 2016 Toyota Highlander is appreciated for its comfort, reliability, and generous features, boasting a powerful V6 engine and a smooth driving experience. ## Why it stands out The 2016 Toyota Highlander continues to impress with its blend of comfort and utility, making it a top choice among midsize SUVs. Its powerful V6 engine provides ample performance for both daily driving and family adventures, combined with a refined ride that enhances passenger comfort. Critically, owners appreciate the spacious interior, accommodating up to seven passengers when the optional third row is in use, along with robust safety ratings. While some users express a desire for more advanced safety features to be standard rather than optional, the Highlander excels in reliability and practicality, core qualities that appeal to families and individuals alike. The integration of Toyota’s Safety Sense technologies further boosts its appeal, providing peace of mind on the road. ## Other model years to consider - **[2022 Toyota Highlander](https://www.cargurus.com/Cars/l-Used-2022-Toyota-Highlander-Chicago-c31996_L7510)** - Average price: $34,421.00 - Good/great deal percentage: 50.5% - User rating: 4.58 / 5 - Total listings: 220 - **[2023 Toyota Highlander](https://www.cargurus.com/Cars/l-Used-2023-Toyota-Highlander-Chicago-c32651_L7510)** - Average price: $34,557.00 - Good/great deal percentage: 49.3% - User rating: 4.36 / 5 - Total listings: 221 - **[2021 Toyota Highlander](https://www.cargurus.com/Cars/l-Used-2021-Toyota-Highlander-Chicago-c30910_L7510)** - Average price: $30,972.00 - Good/great deal percentage: 39.4% - User rating: 4.82 / 5 - Total listings: 165 This analysis is based on CarGurus' proprietary market data from March 19, 2026, CarGurus experts' opinions, and generative AI.