Used 2016 Toyota Highlander for Sale near Chicago, IL

## Summary - With 103 currently listed for sale near Chicago, IL and an **average price of $18,374.00**, 24.3% 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. - **78.6% of 2016 Highlander models on CarGurus are accident free**. - The 2016 Toyota Highlander is known for its comfort, reliability, and a range of features, along with a powerful V6 engine and a smooth ride. ## Why it stands out The 2016 Toyota Highlander is a standout in the midsize SUV segment for its blend of comfort, versatility, and reliable performance. Owners typically rave about its spacious interior and the optional third-row seating, accommodating up to seven passengers. It balances practicality with a solid V6 engine that delivers both power and smooth operation on various terrains. However, while it excels in comfort and versatility, some users note a desire for more advanced safety technology, which is often optional rather than standard. Overall, the Highlander earns high marks for its reputation for reliability and safety, which makes it an appealing choice for families and long-term buyers. ## Other model years to consider - **[2022 Toyota Highlander](https://www.cargurus.com/Cars/l-Used-2022-Toyota-Highlander-Chicago-c31996_L7510)** - Average price: $34,408.00 - Good/great deal percentage: 55.3% - User rating: 4.58 / 5 - Total listings: 226 - **[2023 Toyota Highlander](https://www.cargurus.com/Cars/l-Used-2023-Toyota-Highlander-Chicago-c32651_L7510)** - Average price: $34,813.00 - Good/great deal percentage: 55.8% - User rating: 4.36 / 5 - Total listings: 231 - **[2021 Toyota Highlander](https://www.cargurus.com/Cars/l-Used-2021-Toyota-Highlander-Chicago-c30910_L7510)** - Average price: $31,003.00 - Good/great deal percentage: 45.8% - User rating: 4.82 / 5 - Total listings: 166 This analysis is based on CarGurus' proprietary market data from March 24, 2026, CarGurus experts' opinions, and generative AI.