Used 2020 Toyota Highlander for Sale near Chicago, IL
195 results
CarGurus Analysis:
2020 Toyota Highlander
With 195 currently listed for sale near Chicago, IL and an average price of $28,470.00, 40.5% of 2020 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
Favorably reviewed: Owners rated the 2020 Toyota Highlander 4.6 / 5 stars.
100.0% of 2020 Highlander models on CarGurus are accident free.
The 2020 Toyota Highlander stands out for its spacious interior, impressive advanced safety features, and comfortable ride, making it a great choice for families.
CarGurus Analysis: 2020 Toyota Highlander
overall
Summary
With 195 currently listed for sale near Chicago, IL and an average price of $28,470.00, 40.5% of 2020 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
Favorably reviewed: Owners rated the 2020 Toyota Highlander 4.6 / 5 stars.
100.0% of 2020 Highlander models on CarGurus are accident free.
The 2020 Toyota Highlander stands out for its spacious interior, impressive advanced safety features, and comfortable ride, making it a great choice for families.
Why it stands out
The 2020 Toyota Highlander is distinctively designed for families seeking comfort and reliability. This all-new model features refined aesthetics, advanced technology, and significant enhancements in passenger comfort. With its smooth operation and pristine riding experience, the Highlander offers features reminiscent of luxury vehicles, such as the Lexus. Its spacious cabin accommodates up to eight passengers and boasts an impressive cargo capacity. Although some users mention the front seat comfort and material quality could be better, the vehicle compensates with effective noise insulation and a soft suspension that make it ideal for long-distance travels. Notably, it includes a comprehensive suite of standard safety technologies, ensuring peace of mind for drivers and passengers alike.
Other model years to consider
- Average price: $35,435.00
- Good/great deal percentage: 60.2%
- User rating: 5 / 5
- Total listings: 196
- Average price: $35,196.00
- Good/great deal percentage: 69.4%
- User rating: 4.67 / 5
- Total listings: 209
- Average price: $24,401.00
- Good/great deal percentage: 29.6%
- User rating: 4.76 / 5
- Total listings: 189
This analysis is based on CarGurus' proprietary market data from April 21, 2026, CarGurus experts' opinions, and generative AI.
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4.6 Overall rating
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Sarah T
Reviewed a 2020 Toyota Highlander on Dec 7, 2025
It’s well-equipped, comfortable, and family-friendly SUV with strong safety tech, a smooth ride, and premium touches (thanks to the platinum trim) like a panoramic moonroof, leather seating, and 12” touchscreen. Its V6 offers solid power and decent fuel efficiency for a 3-row SUV, and overall it feels modern, quiet, and refined. It’s a great value if you want a reliable, upscale daily driver! The main thing it’s missing is more usable third-row and cargo space. The 3rd row is tight for adults and cargo behind it is limited. Otherwise, it’s a strong all-around pick and fits exactly what I was looking for. I would compare this to the Kia Telluride, Hyundai Palisade, Honda Pilot, and the Ford Explorer.
Anonymous
Reviewed a 2020 Toyota Highlander on Nov 8, 2020
Most comfortable riding vehicle that we have ever purchased. Great features and a great looking vehicle as well.
Kris B
Reviewed a 2020 Toyota Highlander on May 22, 2023
Absolutely love this car. Great comfortable family vehicle with plenty of space, and features
Lee W
Reviewed a 2020 Toyota Highlander on Feb 28, 2020
The ride was smooth, the Highlander is quick and very quiet. I loved many of the features it had, like the posted speed limit on the instrument cluster. What really disappointed me was the passenger seat comfort. The seat bottom only adjusts fron-to-rear, not up or down so I wasn’t as comfortable in it as I was the Hyundai Palisade or the Kia Telluride. It’s still a really good vehicle.
2020 Toyota Highlander Trims
| Trim type | MSRP |
|---|---|
| L AWD | $36,200 |
| LE FWD | $36,800 |
| Limited FWD | $43,650 |
| LE AWD | $38,400 |
| Limited AWD | $45,600 |
| Platinum AWD | $48,800 |
| XLE FWD | $39,600 |
| XLE AWD | $41,200 |
2020 Toyota Highlander Price Trends
CarGurus tracks the prices of millions of used car listings every year. See how the average price of 2020 Toyota Highlander prices has changed over time.
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