Used 2019 Toyota Highlander for Sale near Chicago, IL

Summary

• With 3,154 currently listed for sale on CarGurus and an average price of $24,132.80, 36.8% 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.
• 66.5% of 2019 Highlander models on CarGurus are accident free.
• The 2019 Toyota Highlander was a stylish midsize SUV that provided seating for up to eight passengers, advanced safety features like adaptive cruise control and automatic emergency braking, and a choice of powerful V6 or hybrid powertrains, all while maintaining high reliability and resale value.

Why it stands out

The 2019 Toyota Highlander excelled in delivering a combination of style, safety, and reliability for family-oriented buyers. With its redesigned muscular shape and spacious interior accommodating up to eight passengers, it provided both comfort and practicality. Additionally, the inclusion of advanced safety features such as adaptive cruise control and automatic emergency braking made it a standout choice in the midsize SUV market, earning top safety ratings year after year.

Other model years to consider

• 2022 Toyota Highlander: This year offers $33,925.22 average price, 34% good/great deals, 4.6/5 user rating, 8.2/10 expert rating, 6,414 listings.
• 2021 Toyota Highlander: This year offers $30,564.27 average price, 35% good/great deals, 4.8/5 user rating, 7.5/10 expert rating, 4,592 listings.
• 2016 Toyota Highlander: This year offers $18,380.51 average price, 38% good/great deals, 4.6/5 user rating, 1,975 listings.

This analysis is based on CarGurus' proprietary market data from December 3, 2025, CarGurus experts' opinions, and generative AI.