New & Used 2026 Toyota Highlander for Sale near Chicago, IL
54 results
CarGurus Analysis:
2026 Toyota Highlander
With 37 currently listed for sale near Chicago, IL and an average price of $50,380.00, 43.2% of 2026 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
97.3% of 2026 Highlander models on CarGurus are accident free.
The 2026 Toyota Highlander continues to offer a spacious and comfortable interior, with available hybrid models delivering exceptional fuel efficiency.
CarGurus Analysis: 2026 Toyota Highlander
Summary
With 37 currently listed for sale near Chicago, IL and an average price of $50,380.00, 43.2% of 2026 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
97.3% of 2026 Highlander models on CarGurus are accident free.
The 2026 Toyota Highlander continues to offer a spacious and comfortable interior, with available hybrid models delivering exceptional fuel efficiency.
Why it stands out
The 2026 Toyota Highlander stands out for its combination of comfort, practicality, and safety features. As a pioneer of the midsize crossover segment, it has consistently provided buyers with a reliable vehicle that balances family-friendly attributes with a smooth ride. The latest iteration maintains this reputation, showcasing refined interior styling and advanced safety technology. Notably, the Highlander offers an optional hybrid powertrain that ranks among the most efficient in its class, attracting eco-conscious buyers. Although the driving dynamics may not excite every enthusiast — with a softer suspension that prioritizes comfort — the Highlander's overall reliability, spaciousness, and impressive safety ratings make it an appealing choice for families and individuals alike.
Other model years to consider
- Average price: $37,140.00
- Good/great deal percentage: 52.8%
- User rating: 5 / 5
- Total listings: 214
- Average price: $35,729.00
- Good/great deal percentage: 50.4%
- User rating: 4.75 / 5
- Total listings: 270
- Average price: $30,052.00
- Good/great deal percentage: 39.9%
- User rating: 4.86 / 5
- Total listings: 223
This analysis is based on CarGurus' proprietary market data from June 9, 2026, CarGurus experts' opinions, and generative AI.
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2026 Toyota Highlander Trims
| Trim type | MSRP |
|---|---|
| Platinum AWD | $53,525 |
| XLE AWD | $45,870 |
| XSE AWD | $47,940 |
| Limited AWD | $50,325 |
2026 Toyota Highlander Price Trends
CarGurus tracks the prices of millions of used car listings every year. See how the average price of 2026 Toyota Highlander prices has changed over time.
See more price trends2026 Toyota Highlander Pricing Analysis: Chicago, IL Market Report
Pricing by Nearby Locations
Market Area: Chicago, IL
Key Insights
- Highest Prices in Suburban Areas: Both Palatine, IL ($51,882) and Aurora, IL ($51,882) command the highest prices, reflecting affluent suburban demand for family vehicles.
- Lower Pricing in Nearby Cities: Cities like Rockford, IL ($43,899) and Janesville, WI ($43,899) offer more affordable options, indicating price sensitivity or higher inventory turnover.
- Consistent Pricing Across Locations: The average prices in cities like Kenosha, WI ($49,394) and Holland, MI ($46,196) are relatively stable, suggesting balanced supply and demand.
City-Level Pricing
| City | Total Listings | Avg Price |
|---|---|---|
| Palatine, IL | 36 | $51,882 |
| Aurora, IL | 35 | $51,882 |
| Kenosha, WI | 55 | $49,394 |
| Rockford, IL | 27 | $43,899 |
| Janesville, WI | 30 | $43,899 |
| Holland, MI | 30 | $46,196 |
| Kalamazoo, MI | 34 | $46,196 |
Pricing by Trim Packages
Key Insights
- AWD Trims Dominate Listings: AWD trims like the XLE AWD (238 listings) have the highest availability, reflecting the demand for all-weather vehicles.
- Price Variation: The Platinum AWD ($53,525 MSRP) is the most expensive trim, offering luxury features, while the XLE AWD ($45,870 MSRP) serves as the benchmark for pricing in the segment.
- Feature-Rich Offerings Lead to Demand: Trims such as Limited AWD and Platinum AWD with advanced features like leather seats and navigation are showing good inventory, indicating buyer preference towards well-equipped models.
Trim-Level Details
| Trim | Listings | MSRP | Drivetrain | Engine |
|---|---|---|---|---|
| XLE AWD | 238 | $45,870 | AWD | 2.4L 265 hp I4 |
| Limited AWD | 104 | $50,325 | AWD | 2.4L 265 hp I4 |
| XSE AWD | 34 | $47,940 | AWD | 2.4L 265 hp I4 |
| Platinum AWD | 47 | $53,525 | AWD | 2.4L 265 hp I4 |
Pricing Analysis by Model Year
Key Insights
- Depreciation Trends Over Time: The 2015 Highlander shows the steepest price drop, with an average price of $17,112, reflecting a -42.2% depreciation from its original MSRP.
- Stronger Retention for Newer Models: The 2025 Highlander is currently valued at $41,202, slightly above its MSRP, indicating steady demand for the latest model.
- Value in Recent Models: Models from 2021 ($29,916) and 2022 ($34,735) present a sweet spot of value with minimal depreciation compared to older years.
Model Year Pricing
| Model Year | Original MSRP | Avg Price | Price vs MSRP |
|---|---|---|---|
| 2025 Toyota Highlander | $40,320 | $41,202 | +2.2% |
| 2024 Toyota Highlander | $39,270 | $37,088 | -5.6% |
| 2023 Toyota Highlander | $36,620 | $36,348 | -0.7% |
| 2022 Toyota Highlander | $35,855 | $34,735 | -3.1% |
| 2021 Toyota Highlander | $35,085 | $29,916 | -14.5% |
| 2020 Toyota Highlander | $34,600 | $28,312 | -18.2% |
| 2019 Toyota Highlander | $31,830 | $25,407 | -20.2% |
| 2018 Toyota Highlander | $31,230 | $23,030 | -26.3% |
| 2017 Toyota Highlander | $30,630 | $20,186 | -34.1% |
| 2016 Toyota Highlander | $30,490 | $19,546 | -35.9% |
| 2015 Toyota Highlander | $29,765 | $17,112 | -42.2% |
These recommendations are based on CarGurus' proprietary market data from June 4, 2026, CarGurus experts' opinions, and generative AI.
