Used 2016 Toyota Highlander for Sale near Chicago, IL

Summary

• With 1,975 currently listed for sale on CarGurus and an average price of $18,380.50, 37.6% of 2016 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
• Favorably reviewed: Owners rated the 2016 Toyota Highlander 4.6 / 5 stars.
• 60% of 2016 Highlander models on CarGurus are accident free.
• The 2016 Toyota Highlander featured a stylish redesign, offered up to eight-passenger seating, and included advanced safety and technology features that set it apart in the midsize SUV segment.

Why it stands out

The 2016 Toyota Highlander stood out in the marketplace by combining stylish design with a robust array of safety features, earning consistent "Top Safety Pick" ratings from IIHS throughout its production. Its generous seating capacity of up to eight passengers and the availability of a powerful yet efficient V6 engine provided families with both versatility and performance. Additionally, the inclusion of advanced technology, even in lower trims, positioned the Highlander as a value-driven choice for those seeking reliability and modern amenities in a midsize SUV.

Other model years to consider

• 2015 Toyota Highlander: This year offers $16,847.20 average price, 34% good/great deals, 4.8/5 user rating, 1,470 listings.
• 2019 Toyota Highlander: This year offers $24,132.82 average price, 37% good/great deals, 4.6/5 user rating, 3,154 listings.
• 2017 Toyota Highlander: This year offers $20,535.56 average price, 39% good/great deals, 4.7/5 user rating, 7.2/10 expert rating, 2,335 listings.

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