New & Used 2025 Toyota Grand Highlander for Sale near Chicago, IL
160 results
CarGurus Analysis:
2025 Toyota Grand Highlander
With 1,629 currently listed for sale and an average price of $47,917.00, 34.3% of 2025 Toyota Grand Highlanders for sale on CarGurus are rated as good or great deals.
93.1% of 2025 Grand Highlander models on CarGurus are accident free.
The 2025 Toyota Grand Highlander offers spacious seating for seven, impressive fuel efficiency with hybrid options, and practicality that appeals to families.
CarGurus Analysis: 2025 Toyota Grand Highlander
Summary
With 1,629 currently listed for sale and an average price of $47,917.00, 34.3% of 2025 Toyota Grand Highlanders for sale on CarGurus are rated as good or great deals.
93.1% of 2025 Grand Highlander models on CarGurus are accident free.
The 2025 Toyota Grand Highlander offers spacious seating for seven, impressive fuel efficiency with hybrid options, and practicality that appeals to families.
Why it stands out
The 2025 Toyota Grand Highlander is a striking addition to Toyota’s SUV lineup, positioned perfectly between the midsize Highlander and the larger Sequoia. With its distinctive design and spacious "adult-sized" third row, it caters especially well to families needing comfort without compromising on style or security. Built on the TNGA-K platform, the Grand Highlander distinguishes itself from the standard Highlander, offering larger dimensions and a modern aesthetic that elevates its interior and exterior looks. It showcases remarkable space where families can enjoy a comfortable ride, alongside impressive fuel efficiency offered by its four-cylinder powertrains, including two hybrid variants. While it presents certain handling drawbacks and some reported early reliability issues, the overall value as a roomy family crossover remains appealing, especially with its strong safety ratings and high accident-free percentage.
Other model years to consider
- Average price: $46,458.00
- Good/great deal percentage: 34.5%
- User rating: 5 / 5
- Total listings: 1,453
- Average price: $52,602.00
- Good/great deal percentage: 33.5%
- Total listings: 677
This analysis is based on CarGurus' proprietary market data from May 25, 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.
2025 Toyota Grand Highlander Trims
| Trim type | MSRP |
|---|---|
| LE AWD | $42,460 |
| Limited FWD | $48,360 |
| Platinum AWD | $54,045 |
| LE FWD | $40,860 |
| XLE FWD | $43,630 |
| Limited AWD | $49,960 |
| XLE AWD | $45,230 |
2025 Toyota Grand Highlander Price Trends
CarGurus tracks the prices of millions of used car listings every year. See how the average price of 2025 Toyota Grand Highlander prices has changed over time.
See more price trends2025 Toyota Grand Highlander Pricing Analysis: Chicago, IL Market Report
Pricing by Nearby Locations
Market Area: Chicago, IL
Key Insights
- Highest Price in Milwaukee: With an average price of $56,499, Milwaukee stands out as the most expensive market, likely driven by lower inventory and higher demand in urban areas.
- Competitive Pricing in Palatine and Aurora: Both cities present the same average price of $47,700 while maintaining a healthy inventory of 65 listings each, suggesting a competitive market balance.
- Kenosha Offers a Premium: Averaging $53,519, Kenosha's slightly elevated price reflects possible regional demand and less availability compared to other surrounding markets.
City-Level Pricing
| City | Total Listings | Avg Price |
|---|---|---|
| Milwaukee, WI | 51 | $56,499 |
| Kenosha, WI | 65 | $53,519 |
| Rockford, IL | 52 | $50,539 |
| Holland, MI | 53 | $57,302 |
| Kalamazoo, MI | 61 | $57,302 |
| Palatine, IL | 65 | $47,700 |
| Aurora, IL | 64 | $47,700 |
Pricing by Trim Packages
Key Insights
- AWD Variants Dominate Inventory: AWD trims, particularly the XLE AWD with 36 listings, represent strong demand, aligning with consumer preferences for utility vehicles.
- Premium Trim Price Gap: The Platinum AWD trim commands the highest MSRP at $54,045, indicating significant markup due to luxury features and exclusive options.
- Limited Availability of Base Trims: Both FWD trims (LE FWD and LE AWD) show minimal listings (1 each), suggesting limited retail strategy for lower-priced options in the current market.
Trim-Level Details
| Trim | Listings | MSRP | Drivetrain | Engine |
|---|---|---|---|---|
| XLE AWD | 36 | $45,230 | AWD | 2.4L 265 hp I4 |
| Platinum AWD | 16 | $54,045 | AWD | 2.4L 265 hp I4 |
| Limited AWD | 19 | $49,960 | AWD | 2.4L 265 hp I4 |
| XLE FWD | 11 | $43,630 | FWD | 2.4L 265 hp I4 |
| Limited FWD | 7 | $48,360 | FWD | 2.4L 265 hp I4 |
| LE FWD | 1 | $40,860 | FWD | 2.4L 265 hp I4 |
| LE AWD | 1 | $42,460 | AWD | 2.4L 265 hp I4 |
These recommendations are based on CarGurus' proprietary market data from May 28, 2026, CarGurus experts' opinions, and generative AI.
