New & Used 2025 Toyota Highlander for Sale near Chicago, IL
133 results
CarGurus Analysis:
2025 Toyota Highlander
With 108 currently listed for sale near Chicago, IL and an average price of $45,801.00, 48.1% of 2025 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
100.0% of 2025 Highlander models on CarGurus are accident free.
The 2025 Toyota Highlander continues to impress with its reliability and spacious interior, making it an excellent family SUV choice.
CarGurus Analysis: 2025 Toyota Highlander
Summary
With 108 currently listed for sale near Chicago, IL and an average price of $45,801.00, 48.1% of 2025 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
100.0% of 2025 Highlander models on CarGurus are accident free.
The 2025 Toyota Highlander continues to impress with its reliability and spacious interior, making it an excellent family SUV choice.
Why it stands out
The 2025 Toyota Highlander stands out in the competitive midsize SUV segment due to its exceptional reputation for reliability and its spacious, family-friendly interior. As a pioneer in the crossover SUV market, the Highlander combines the efficiency of a unibody construction with the capabilities of a traditional SUV, offering a smooth ride and versatile seating options. The model maintains a strong emphasis on safety, boasting a 100% accident-free record among current listings. While it may not be the most exhilarating vehicle to drive, buyers appreciate its practical features, robust safety ratings, and substantial cargo space, making it ideal for families and commuters alike.
Other model years to consider
- Average price: $34,752.00
- Good/great deal percentage: 64.1%
- User rating: 5 / 5
- Total listings: 198
- Average price: $35,668.00
- Good/great deal percentage: 70.2%
- User rating: 4.75 / 5
- Total listings: 225
- Average price: $24,235.00
- Good/great deal percentage: 36.9%
- User rating: 4.76 / 5
- Total listings: 187
This analysis is based on CarGurus' proprietary market data from May 12, 2026, CarGurus experts' opinions, and generative AI.
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2025 Toyota Highlander Trims
| Trim type | MSRP |
|---|---|
| LE FWD | $40,320 |
| Limited FWD | $47,575 |
| Limited AWD | $49,525 |
| LE AWD | $41,920 |
| Platinum AWD | $52,725 |
| XSE AWD | $47,140 |
| XLE AWD | $45,070 |
| XLE FWD | $43,470 |
2025 Toyota Highlander Price Trends
CarGurus tracks the prices of millions of used car listings every year. See how the average price of 2025 Toyota Highlander prices has changed over time.
See more price trends2025 Toyota 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 commands an average price of $47,180, likely due to lower inventory and higher demand.
- Best Value in Rockford, IL: Rockford offers the lowest average price at $39,506, suggesting higher inventory levels and competitive market conditions.
- Price Variability: Cities like Aurora and Palatine show moderate average prices around $45K, indicating stable demand and inventory levels.
City-Level Pricing
| City | Total Listings | Avg Price |
|---|---|---|
| Holland, MI | 60 | $47,180 |
| Aurora, IL | 101 | $45,771 |
| Palatine, IL | 99 | $44,876 |
| South Bend, IN | 65 | $45,199 |
| Kenosha, WI | 121 | $42,632 |
| Milwaukee, WI | 88 | $40,819 |
| Janesville, WI | 64 | $40,692 |
| Lafayette, IN | 86 | $41,359 |
| Rockford, IL | 67 | $39,506 |
Pricing by Trim Packages
Key Insights
- XLE AWD Leads in Supply: The XLE AWD trim shows strong market position with 209 listings, suggesting robust consumer preference for this model.
- Price Differences Across Trims: There is a noticeable price range; the Limited AWD ($49,525 MSRP) is priced significantly higher than the LE FWD ($40,320 MSRP), reflecting premium features and luxury.
- AWD Popularity: AWD trims dominate listings, aligning with consumer demand for improved performance and handling in various driving conditions.
Trim-Level Details
| Trim | Listings | MSRP | Drivetrain | Engine |
|---|---|---|---|---|
| XLE AWD | 209 | $45,070 | AWD | 2.4L 265 hp I4 |
| Limited AWD | 104 | $49,525 | AWD | 2.4L 265 hp I4 |
| XLE FWD | 45 | $43,470 | FWD | 2.4L 265 hp I4 |
| LE FWD | 50 | $40,320 | FWD | 2.4L 265 hp I4 |
| LE AWD | 76 | $41,920 | AWD | 2.4L 265 hp I4 |
| XSE AWD | 37 | $47,140 | AWD | 2.4L 265 hp I4 |
| Platinum AWD | 34 | $52,725 | AWD | 2.4L 265 hp I4 |
| Limited FWD | 21 | $47,575 | FWD | 2.4L 265 hp I4 |
Pricing Analysis by Model Year
Key Insights
- Recent Models Retain Value: The 2026 Highlander currently leads in pricing at $50,960, indicating strong demand for newer models and limited supply.
- Significant Depreciation for Older Models: The 2015 model shows substantial depreciation with an average price of $16,945, reflecting nearly 43% drop from its original MSRP.
- Value Opportunities in Mid-Age Models: Models from 2021 and 2022 provide a balance of pricing and feature set, with prices just slightly below their MSRPs, indicating reasonable value for buyers.
Model Year Pricing
| Model Year | Original MSRP | Avg Price | Price vs MSRP |
|---|---|---|---|
| 2026 Toyota Highlander | $45,870 | $50,960 | +11.7% |
| 2024 Toyota Highlander | $39,270 | $35,124 | -10.9% |
| 2023 Toyota Highlander | $36,620 | $35,854 | -2.1% |
| 2022 Toyota Highlander | $35,855 | $34,095 | -4.9% |
| 2021 Toyota Highlander | $35,085 | $30,630 | -12.7% |
| 2020 Toyota Highlander | $34,600 | $29,316 | -15.3% |
| 2019 Toyota Highlander | $31,830 | $24,202 | -23.9% |
| 2018 Toyota Highlander | $31,230 | $23,501 | -24.8% |
| 2017 Toyota Highlander | $30,630 | $20,395 | -33.5% |
| 2016 Toyota Highlander | $30,490 | $20,558 | -32.6% |
| 2015 Toyota Highlander | $29,765 | $16,945 | -43.1% |
These recommendations are based on CarGurus' proprietary market data from May 14, 2026, CarGurus experts' opinions, and generative AI.
