Used 2019 Toyota Highlander for Sale near Chicago, IL

Summary

• With 3,041 currently listed for sale on CarGurus and an average price of $23,940.50, 35.6% of 2019 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
• Favorably reviewed: Owners rated the 2019 Toyota Highlander 4.6 / 5 stars.
• 66.3% of 2019 Highlander models on CarGurus are accident free.
• The 2019 Toyota Highlander featured a stylish design, offered spacious seating for up to eight, and included advanced safety technology, making it a reliable choice for families.

Why it stands out

The 2019 Toyota Highlander distinguished itself in the midsize SUV segment with its combination of stylish design and family-friendly features, offering an eight-passenger seating option for larger families. It provided a suite of advanced safety technologies, including adaptive cruise control and automatic emergency braking, making it a standout choice for safety-conscious buyers. Additionally, its reliable performance, bolstered by a powerful V6 engine and competitive fuel efficiency, ensured that it maintained strong resale value in the market.

Other model years to consider

• 2022 Toyota Highlander: This year offers $33,572.41 average price, 36% good/great deals, 4.6/5 user rating, 8.2/10 expert rating, 6,308 listings.
• 2021 Toyota Highlander: This year offers $30,215.79 average price, 36% good/great deals, 4.8/5 user rating, 7.5/10 expert rating, 4,417 listings.
• 2016 Toyota Highlander: This year offers $18,438.19 average price, 39% good/great deals, 4.6/5 user rating, 1,955 listings.

This analysis is based on CarGurus' proprietary market data from December 16, 2025, CarGurus experts' opinions, and generative AI.