New Toyota Highlander for Sale near Chicago, IL
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Customer summary
Overall, the Toyota Highlander has built a strong reputation across its model years for reliability, comfort, and family-friendly features. Drivers appreciate its spacious interiors and smooth rides, often highlighting its impressive safety features as a key asset. Many also enjoy the performance and power of the engines. However, some common criticisms include a lack of advanced infotainment options in older models, tight third-row seating, and varying cargo space depending on configuration. Overall, the Highlander is seen as a dependable choice for families and an excellent value in the SUV market.
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4.7 Overall rating
Customers say
Overall, the Toyota Highlander has built a strong reputation across its model years for reliability, comfort, and family-friendly features. Drivers appreciate its spacious interiors and smooth rides, often highlighting its impressive safety features as a key asset. Many also enjoy the performance and power of the engines. However, some common criticisms include a lack of advanced infotainment options in older models, tight third-row seating, and varying cargo space depending on configuration. Overall, the Highlander is seen as a dependable choice for families and an excellent value in the SUV market.
AI generated from the text of customer reviews.
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Anonymous
Reviewed a 2024 Toyota XLE AWD on Dec 10, 2025
The 2024 Toyota Highlander XLE offers insane cabin room, comfort and luxury feel. The chassis makes an absolute smooth, dream and comfortable ride. Cabin rear chairs makes four adults feel like your in a Sequoia with room. Absolute beautiful and enjoyable ride and purchase
Jamey F
Reviewed a 2024 Toyota Highlander on Sep 6, 2025
I truly like everything about this vehicle. All the features are very easy to use and very comfortable.
Toyota Highlander Trims
| Trim type | MSRP |
|---|---|
| 2026 Platinum AWD | $53,525 |
| 2026 XLE AWD | $45,870 |
| 2026 XSE AWD | $47,940 |
| 2026 Limited AWD | $50,325 |
Toyota Highlander Price Trends
CarGurus tracks the prices of millions of car listings every year. See how the average price of prices has changed over time.
See more price trendsToyota Highlander Pricing Analysis: Chicago, IL Market Report
Pricing Analysis by Model Year
Key Insights
- Premium for Latest Models: The 2026 Highlander is priced at $51,280, showing a high demand with a depreciation of only +11.0% above MSRP.
- Sharp Decline in Older Model Pricing: The 2019 Highlander shows a significant depreciation at -24.4%, priced at $24,080, reflecting a steep drop in value as models age.
- Stable Pricing Around Recent Models: The 2023 Highlander maintains a close average to its MSRP at $36,714, with only +0.3% depreciation, indicating a solid demand for newer models.
Model Year Pricing
| Model Year | Original MSRP | Avg Price | Price vs MSRP |
|---|---|---|---|
| 2026 Toyota Highlander | $45,870 | $51,280 | +11.0% |
| 2025 Toyota Highlander | $40,320 | $43,002 | +6.7% |
| 2024 Toyota Highlander | $39,270 | $35,242 | -10.5% |
| 2023 Toyota Highlander | $36,620 | $36,714 | +0.3% |
| 2022 Toyota Highlander | $35,855 | $34,995 | -2.4% |
| 2021 Toyota Highlander | $35,085 | $30,352 | -13.4% |
| 2020 Toyota Highlander | $34,600 | $29,898 | -13.5% |
| 2019 Toyota Highlander | $31,830 | $24,080 | -24.4% |
| 2018 Toyota Highlander | $31,230 | $23,317 | -25.4% |
| 2017 Toyota Highlander | $30,630 | $20,930 | -31.7% |
| 2016 Toyota Highlander | $30,490 | $20,458 | -32.9% |
Pricing in Nearby Cities
Market Area: Greater Chicago Region
Key Insights
- Highest Average Price in South Bend: The South Bend (IN) market reflects the highest average price of $32,155, likely due to lower inventory amidst greater demand.
- Lowest Prices in Janesville and Aurora: Cities like Janesville (WI) and Aurora (IL) offer the most competitive pricing at $25,003 and $25,323 respectively, hinting at higher inventory levels and competitive market dynamics.
- Price Variance Influenced by Inventory Levels: The broader inventory in cities like Milwaukee (WI) with 605 listings stabilizes average pricing around $27,181, showcasing how inventory influences value.
City-Level Pricing
| City | Total Listings | Avg Price |
|---|---|---|
| South Bend, IN | 616 | $32,155 |
| Milwaukee, WI | 605 | $27,181 |
| Kalamazoo, MI | 615 | $30,334 |
| Holland, MI | 588 | $28,804 |
| Lafayette, IN | 707 | $29,444 |
| Rockford, IL | 578 | $25,489 |
| Palatine, IL | 352 | $25,619 |
| Aurora, IL | 338 | $25,323 |
| Kenosha, WI | 313 | $26,325 |
| Janesville, WI | 573 | $25,003 |
Pricing by Trim Packages
Key Insights
- XLE AWD Dominates Listings: The XLE AWD trim leads with 219 listings, indicating strong demand for this feature-rich option within the market.
- Limited AWD Premium Pricing: The Limited AWD trim is priced at $50,325, representing a ~10.0% premium compared to the average MSRP across trims, reflecting higher-end features and luxury appeal.
- Variability in Trim Popularity: The spread of trim prices illustrates consumer preference, with the base trims like XLE AWD being more accessible compared to higher trims like Platinum AWD priced at $53,525.
Trim-Level Details
| Trim | Listings | MSRP | Drivetrain | Engine |
|---|---|---|---|---|
| XLE AWD | 219 | $45,870 | AWD | 2.4L 265 hp I4 |
| Limited AWD | 103 | $50,325 | AWD | 2.4L 265 hp I4 |
| XSE AWD | 34 | $47,940 | AWD | 2.4L 265 hp I4 |
| Platinum AWD | 44 | $53,525 | AWD | 2.4L 265 hp I4 |
These recommendations are based on CarGurus' proprietary market data from May 21, 2026, CarGurus experts' opinions, and generative AI.
