Used 2021 Toyota Highlander for Sale near Chicago, IL
176 results
CarGurus Analysis:
2021 Toyota Highlander
With 180 currently listed for sale near Chicago, IL and an average price of $30,961.00, 54.4% of 2021 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
Favorably reviewed: Owners rated the 2021 Toyota Highlander 4.86 / 5 stars.
100.0% of 2021 Highlander models on CarGurus are accident free.
The 2021 Toyota Highlander features a smooth ride, ample interior space, and a suite of advanced safety technologies.
CarGurus Analysis: 2021 Toyota Highlander
overall
Summary
With 180 currently listed for sale near Chicago, IL and an average price of $30,961.00, 54.4% of 2021 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
Favorably reviewed: Owners rated the 2021 Toyota Highlander 4.86 / 5 stars.
100.0% of 2021 Highlander models on CarGurus are accident free.
The 2021 Toyota Highlander features a smooth ride, ample interior space, and a suite of advanced safety technologies.
Why it stands out
The 2021 Toyota Highlander is designed for families who prioritize safety, comfort, and reliability in their vehicles. With an excellent user rating of 4.86, it has captured the attention of drivers looking for a spacious three-row SUV. Its robust 3.5-liter V6 engine delivers 295 horsepower and works seamlessly with an eight-speed automatic transmission, providing both efficiency and capable performance. The Highlander also stands out with a 100% accident-free rate in listings, reinforcing its reputation for reliability.
The introduction of advanced safety features under the Toyota Safety Sense 2.5+ suite enhances driver confidence, making it a great choice for family transport. Additionally, the Highlander maintains modern styling that distinguishes it from typical rivals while offering a comfortable and tech-savvy interior. However, potential buyers should be aware of its less sporty driving dynamics and a somewhat uninspired base engine.
Other model years to consider
- Average price: $34,107.00
- Good/great deal percentage: 59.7%
- User rating: 5 / 5
- Total listings: 196
- Average price: $35,886.00
- Good/great deal percentage: 64.7%
- User rating: 4.75 / 5
- Total listings: 224
- Average price: $23,966.00
- Good/great deal percentage: 36.6%
- User rating: 4.76 / 5
- Total listings: 194
This analysis is based on CarGurus' proprietary market data from May 5, 2026, CarGurus experts' opinions, and generative AI.
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4.9 Overall rating
Filter by rating
Julie W
Reviewed a 2021 Toyota Highlander on Jul 20, 2024
I loved my Highlander. I give my 2021 Toyota Highlander a 100 out of 10 on its safety. My car was a limited and it had most bells and whistles which I loved but what I loved most was that we all walked away from a collision where we were traveling 40 miles an hour and thanks to the safety design , we’re here.
Jimmy K
Reviewed a 2021 Toyota Highlander on May 31, 2024
Drives great and has all the tech you need. I have a limited V6.
Terry S
Reviewed a 2021 Toyota Highlander on May 29, 2024
They seem to be good from all other reviews but this particular one had a very bad smoke smell might be able to get the smell out dont know but seems ok other than that
Tony T
Reviewed a 2021 Toyota Highlander on Jul 5, 2022
Love this 2021 Highlander SXE model, got all the bells and whistles. No complaints. Can’t go wrong with Toyota. Out of the 20 SUV with 5000 lbs towing, this one is top IMO.
2021 Toyota Highlander Trims
| Trim type | MSRP |
|---|---|
| LE FWD | $37,285 |
| LE AWD | $38,885 |
| XSE FWD | $41,680 |
| XSE AWD | $43,630 |
| Limited AWD | $45,990 |
| Platinum AWD | $49,190 |
| XLE FWD | $40,085 |
| XLE AWD | $41,685 |
2021 Toyota Highlander Price Trends
CarGurus tracks the prices of millions of used car listings every year. See how the average price of 2021 Toyota Highlander prices has changed over time.
See more price trends2021 Toyota Highlander Pricing Analysis: Chicago, IL Market Report
Pricing by Nearby Locations
Market Area: Chicago, IL
Key Insights
- Highest Price in Janesville: The average price in Janesville, WI ($31,585) stands out as the highest, likely reflecting a premium market due to limited availability.
- Lowest Prices in South Bend: In contrast, South Bend, IN ($29,823) presents the most budget-friendly option, suggesting a more price-sensitive local demand.
- Price Consistency Among Cities: Most nearby locations maintain an average price range of approximately $30,000 to $32,000, indicating stable pricing across the region.
City-Level Pricing
| City | Total Listings | Avg Price |
|---|---|---|
| Janesville, WI | 135 | $31,585 |
| Palatine, IL | 180 | $31,412 |
| Aurora, IL | 179 | $31,024 |
| Rockford, IL | 134 | $30,757 |
| Kenosha, WI | 166 | $30,284 |
| Milwaukee, WI | 148 | $30,074 |
| Holland, MI | 138 | $30,796 |
| Kalamazoo, MI | 139 | $32,245 |
| Lafayette, IN | 166 | $31,859 |
| South Bend, IN | 139 | $29,823 |
Pricing by Trim Packages
Key Insights
- Dominant Trim: The XLE AWD (209 listings) is the most common trim, highlighting its desirability and likely reflecting regional preferences for all-wheel drive capabilities.
- Price Variation Among Trims: The Limited AWD ($45,990 MSRP) is significantly more expensive, indicating a premium associated with luxury features such as leather seats and advanced tech.
- Popularity of AWD: Trims equipped with AWD see higher inventory, reinforcing trends towards all-weather functionality in buyer preferences.
Trim-Level Details
| Trim | Listings | MSRP | Drivetrain | Engine |
|---|---|---|---|---|
| XLE AWD | 209 | $41,685 | AWD | 3.5L 295 hp V6 |
| Limited AWD | 96 | $45,990 | AWD | 3.5L 295 hp V6 |
| LE AWD | 80 | $38,885 | AWD | 3.5L 295 hp V6 |
| XLE FWD | 52 | $40,085 | FWD | 3.5L 295 hp V6 |
| LE FWD | 59 | $37,285 | FWD | 3.5L 295 hp V6 |
| XSE AWD | 33 | $43,630 | AWD | 3.5L 295 hp V6 |
| Platinum AWD | 34 | $49,190 | AWD | 3.5L 295 hp V6 |
| Limited FWD | 21 | $44,040 | FWD | 3.5L 295 hp V6 |
Pricing Analysis by Model Year
Key Insights
- 2026 Model Premium: The 2026 Toyota Highlander shows a current average price of $51,495, which is approximately 12.2% above MSRP, indicating strong demand for the latest model.
- Depreciation Trends: Older models experience significant depreciation, with the 2019 Highlander priced at $24,199, which is about -24.5% vs MSRP.
- Best Value Years: The 2022 and 2023 models offer moderate depreciation, making them appealing choices with prices around $33,550 to $36,517, reflecting a good balance of price and features.
Model Year Pricing
| Model Year | Original MSRP | Avg Price | Price vs MSRP |
|---|---|---|---|
| 2026 Toyota | $45,870 | $51,495 | +12.2% |
| 2025 Toyota | $40,320 | $45,796 | +13.7% |
| 2024 Toyota | $39,270 | $34,603 | -11.9% |
| 2023 Toyota | $36,620 | $36,517 | -0.3% |
| 2022 Toyota | $35,855 | $33,550 | -6.4% |
| 2020 Toyota | $34,600 | $28,681 | -17.1% |
| 2019 Toyota | $31,830 | $24,199 | -24.5% |
| 2018 Toyota | $31,230 | $23,427 | -25.0% |
| 2017 Toyota | $30,630 | $20,404 | -33.4% |
| 2016 Toyota | $30,490 | $19,530 | -35.9% |
| 2015 Toyota | $29,765 | $18,510 | -37.7% |
These recommendations are based on CarGurus' proprietary market data from May 8, 2026, CarGurus experts' opinions, and generative AI.
