New & Used 2026 Toyota Grand Highlander for Sale near Chicago, IL
123 results
CarGurus Analysis:
2026 Toyota Grand Highlander
With 660 currently listed for sale and an average price of $52,748.00, 34.5% of 2026 Toyota Grand Highlanders for sale on CarGurus are rated as good or great deals.
96.7% of 2026 Grand Highlander models on CarGurus are accident free.
The 2026 Toyota Grand Highlander offers a spacious third row, standard advanced safety features, and multiple powertrain options.
CarGurus Analysis: 2026 Toyota Grand Highlander
overall
Summary
With 660 currently listed for sale and an average price of $52,748.00, 34.5% of 2026 Toyota Grand Highlanders for sale on CarGurus are rated as good or great deals.
96.7% of 2026 Grand Highlander models on CarGurus are accident free.
The 2026 Toyota Grand Highlander offers a spacious third row, standard advanced safety features, and multiple powertrain options.
Why it stands out
The 2026 Toyota Grand Highlander distinguishes itself in the crowded three-row crossover market with its combination of spaciousness and practicality. As an option for families needing extra room, it provides ample legroom, especially in the third row, making it comfortable for all passengers—even on long trips. The availability of hybrid powertrain options appeals to those looking for better fuel efficiency, with the standard hybrid achieving up to 36 mpg combined. Additionally, its roster of advanced safety features, part of Toyota Safety Sense 3.0, ensures that families can travel with peace of mind.
Despite some limitations, such as uninspired exterior styling and certain technology features being tied to subscriptions, the Grand Highlander remains a top contender for buyers prioritizing safety, efficiency, and interior space. It adeptly fulfills the needs of active families while offering a well-rounded experience.
Other model years to consider
- Average price: $46,480.00
- Good/great deal percentage: 35.3%
- User rating: 5 / 5
- Total listings: 1,391
- Average price: $47,803.00
- Good/great deal percentage: 34.5%
- Total listings: 1,556
This analysis is based on CarGurus' proprietary market data from May 18, 2026, CarGurus experts' opinions, and generative AI.
Relevant articles
2026 CarGurus Confidence Awards — Best Family Upgrade: Toyota Grand Highlander
The Toyota Grand Highlander wins the 2026 CarGurus Confidence Award for Best Family Upgrade. A usable third row, 98 cu ft of cargo space, and three powertrains for every family.
The Best Toyota SUVs of 2026
Toyota is one of the world's largest and most popular automakers, and it builds a huge array of vehicles. In the U.S., it offers no fewer than nine different SUVs, many of which are built in America. Here, we detail how they stack up.
The Best Crossover SUVs of 2026
Over the past decade, crossover SUVs have come to dominate American roads. With more than eight different models on offer, choosing the right one can be daunting, but there’s a good fit for almost every purse and purpose if you do your research.
2026 Toyota Grand Highlander Trims
| Trim type | MSRP |
|---|---|
| Platinum AWD | $55,045 |
| LE AWD | $43,460 |
| LE FWD | $41,860 |
| Limited AWD | $50,960 |
| Limited FWD | $49,360 |
| XLE AWD | $46,230 |
| XLE FWD | $44,630 |
2026 Toyota Grand Highlander Price Trends
CarGurus tracks the prices of millions of used car listings every year. See how the average price of 2026 Toyota Grand Highlander prices has changed over time.
See more price trends2026 Toyota Grand Highlander Pricing Analysis: Chicago, IL Market Report
Pricing by Nearby Locations
Market Area: Chicago, IL
Key Insights
- Highest Prices in Holland, MI: The market in Holland has the highest average price at $60,104, likely driven by limited inventory or higher demand for premium features.
- Lowest Prices in Palatine and Kenosha: Both Palatine, IL and Kenosha, WI have the lowest average price at $49,487, suggesting stronger competition or better value offerings.
- Inventory Variability: Listings in Lafayette, IN (36) and Aurora, IL (26) show how inventory levels correlate with prices, indicating regional consumer preferences and demand.
City-Level Pricing
| City | Total Listings | Avg Price |
|---|---|---|
| Holland, MI | 29 | $60,104 |
| Lafayette, IN | 36 | $59,222 |
| Aurora, IL | 26 | $51,742 |
| Kalamazoo, MI | 29 | $60,104 |
| Palatine, IL | 33 | $49,487 |
| Kenosha, WI | 34 | $49,487 |
Pricing by Trim Packages
Key Insights
- Inventory Concentration in AWD Trims: The XLE AWD with 36 listings makes it the most available trim, confirming its popularity among consumers.
- Price Disparity Among Trims: The Platinum AWD has the highest MSRP at $55,045, reflecting its additional luxury features that justify the higher cost.
- Limited Inventory in FWD Options: The Limited FWD trim, with only 3 listings, illustrates the less demand for front-wheel drive options compared to all-wheel drive.
Trim-Level Details
| Trim | Listings | MSRP | Drivetrain | Engine |
|---|---|---|---|---|
| XLE AWD | 36 | $46,230 | AWD | 2.4L 265 hp I4 |
| Platinum AWD | 20 | $55,045 | AWD | 2.4L 265 hp I4 |
| XLE FWD | 13 | $44,630 | FWD | 2.4L 265 hp I4 |
| Limited AWD | 19 | $50,960 | AWD | 2.4L 265 hp I4 |
| Limited FWD | 3 | $49,360 | FWD | 2.4L 265 hp I4 |
| LE FWD | 5 | $41,860 | FWD | 2.4L 265 hp I4 |
| LE AWD | 1 | $43,460 | AWD | 2.4L 265 hp I4 |
These recommendations are based on CarGurus' proprietary market data from May 14, 2026, CarGurus experts' opinions, and generative AI.
