New & Used 2025 Toyota Highlander for Sale near Chicago, IL

## Summary - With 110 currently listed for sale near Chicago, IL and an **average price of $39,356.00**, 38.2% of 2025 Toyota Highlanders for sale on CarGurus are rated as good or great deals. - **83.6% of 2025 Highlander models on CarGurus are accident free**. - The 2025 Toyota Highlander features a spacious and comfortable interior, an available hybrid model, and impressive safety ratings. ## Why it stands out The 2025 Toyota Highlander distinguishes itself in the crowded SUV market with its roomy and versatile interior, perfect for families or those needing extra cargo space. The Highlander offers a smooth, car-like ride thanks to its unibody construction, which contributes to better fuel efficiency compared to traditional body-on-frame SUVs. While it may not excite driving enthusiasts with its uninspired dynamics, its reliability, safety, and practicality are standout features. The introduction of advanced safety tech and a new turbocharged engine has improved overall efficiency while maintaining a competitive edge among midsize SUVs. The Highlander's robust reputation for longevity and family-friendly features makes it a wise choice for buyers seeking a dependable used vehicle. ## 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.