New & Used 2026 Toyota Highlander for Sale nearChicago, IL

Is the 2026 Toyota Highlander a good car?

The 2026 Toyota Highlander is a comfortable, practical midsize SUV that puts everyday usefulness ahead of excitement. Toyota says all-wheel drive is standard across the lineup for 2026, and the Highlander’s core strengths remain a smooth ride, strong practicality, and a reputation for reliability and safety.

It also gives you up to 84.3 cubic feet of cargo space with the seats folded, which supports its role as a sensible family hauler. Standard equipment includes an 8-inch touchscreen, USB inputs, Apple CarPlay, Android Auto, Amazon Alexa, and Toyota Safety Sense, so you get a well-rounded feature set without having to move up the lineup.

The tradeoff is that it still isn’t especially engaging to drive, and Toyota’s tech can be frustrating to use. Even so, if you want comfort, efficiency, and a family-friendly SUV that covers the basics well, the Highlander makes a strong case for itself. Market availability is also decent, with 35.0% of listings marked as good or great deals.

Is the 2026 Toyota Highlander reliable?

The 2026 Toyota Highlander is presented as a reliability-minded SUV with a reputation for safety and long-term dependability. Toyota’s emphasis on practicality, comfort, and a well-rounded ownership experience supports that image, and the model continues to lean on the same strengths that have long made it appealing to families.

It also comes with Toyota Safety Sense and a straightforward standard equipment set, which fits the Highlander’s low-drama character. For used buyers, that usually points to lower long-term ownership risk than you might expect from a more complicated or performance-focused SUV.

What should I look for when buying a used 2026 Toyota Highlander?

Accident-free inventory is excellent at 94.9% — clean inventory, standard diligence applies.

You should still run a vehicle history report and prioritize a pre-purchase inspection, especially if you’re comparing multiple listings. Focus on overall condition, maintenance records, and whether the vehicle’s features and equipment work as expected, since a clean history does not replace a careful mechanical check.

Is now a good time to buy a used 2026 Toyota Highlander?

This looks like a moderate, selective buyer’s market, so you have room to shop carefully rather than rush.

• Deal availability: 35.0% of listings are priced as good or great deals.
• Inventory: There are 809 listings available.
• Clean inventory: 94.9% of listings are accident-free.

Should I buy a 2026 Toyota Highlander or consider a different year?

If you're weighing the 2026 against nearby model years, here's how to think about it:

Choose the 2026 if:

• 35.0% of listings are priced as good or great deals.
• Accident-free inventory is excellent at 94.9% — clean inventory, standard diligence applies.

The bottom line: If you want the strongest mix of standard all-wheel drive, family-friendly practicality, and current-year availability, the 2026 Toyota Highlander is the primary path to consider. If you’re more price-sensitive, a nearby model year may give you a lower entry point while still keeping the Highlander’s core comfort-and-utility formula intact.

These recommendations are based on CarGurus' proprietary market data from September 15, 2026, CarGurus experts' opinions, and generative AI.