Used Toyota Highlander for Sale near Chicago, IL
24 results
2027 Toyota Highlander Price Trends
CarGurus tracks the prices of millions of used car listings every year. See how the average price of 2027 Toyota Highlander prices has changed over time.
See more price trendsAVG Price
Not Available
2027 Toyota Highlander
Index Price
$29,207
0.7%
All used vehicles
2027 Toyota Highlander Pricing Analysis: Chicago, IL Market Report
Pricing Analysis by Model Year
Key Insights
- Current Premium for New Models: The 2026 Highlander is priced at $50,380, about 9.3% above its original MSRP of $45,870, indicating strong market demand for newer generations.
- Significant Depreciation in Older Models: The 2019 Highlander shows a price decline of ~21%, underscoring steep depreciation over time.
- Best Value Exists in Recent Models: Models from 2020 to 2022 offer a balance of value and price stability, with depreciation rates below ~10%; specifically, 2021 is down ~13.4% vs MSRP.
Model Year Pricing
| Model Year | Original MSRP | Avg Price | Price vs MSRP |
|---|---|---|---|
| 2026 Toyota Highlander | $45,870 | $50,380 | +9.3% |
| 2025 Toyota Highlander | $40,320 | $41,070 | +1.9% |
| 2024 Toyota Highlander | $39,270 | $36,614 | -6.8% |
| 2023 Toyota Highlander | $36,620 | $35,926 | -1.9% |
| 2022 Toyota Highlander | $35,855 | $34,885 | -3.0% |
| 2021 Toyota Highlander | $35,085 | $30,375 | -13.4% |
| 2020 Toyota Highlander | $34,600 | $28,000 | -19.3% |
| 2019 Toyota Highlander | $31,830 | $25,176 | -21.0% |
| 2018 Toyota Highlander | $31,230 | $23,254 | -25.5% |
| 2017 Toyota Highlander | $30,630 | $20,373 | -33.5% |
| 2016 Toyota Highlander | $30,490 | $19,520 | -35.9% |
| 2015 Toyota Highlander | $29,765 | $17,324 | -41.7% |
These recommendations are based on CarGurus' proprietary market data from June 11, 2026, CarGurus experts' opinions, and generative AI.
FAQs
How many 2027 Toyota Highlander vehicles in Chicago, IL have no reported accidents or damage?
6 out of 6 for sale near Chicago, IL have no reported accidents or damage.
What is the fuel economy of the 2027 Toyota Highlander?
Depending on the engine and options, the 2027 Toyota Highlander gets between 24 and 24 MPG (or EV battery range).
What fuel types are available?
Gasoline engines are available.
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