Used 2020 Toyota Highlander for Sale near Chicago, IL
189 results
CarGurus Analysis:
2020 Toyota Highlander
With 181 currently listed for sale near Chicago, IL and an average price of $28,383.00, 40.3% 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.
116.0% of 2020 Highlander models on CarGurus are accident-free.
The 2020 Toyota Highlander offers a spacious interior, advanced safety features, and a comfortable ride.
CarGurus Analysis: 2020 Toyota Highlander
overall
Summary
With 181 currently listed for sale near Chicago, IL and an average price of $28,383.00, 40.3% 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.
116.0% of 2020 Highlander models on CarGurus are accident-free.
The 2020 Toyota Highlander offers a spacious interior, advanced safety features, and a comfortable ride.
Why it stands out
The 2020 Toyota Highlander is a well-rounded midsize SUV that excels in passenger comfort and safety. Redesigned for 2020, it features an upscale interior that rivals luxury vehicles, with quality materials and various technology enhancements that bolster its appeal. Notably, the Highlander offers a smooth ride courtesy of its 3.5-liter V6 engine, which delivers 295 horsepower, providing brisk acceleration. Despite some criticisms regarding handling and insulation from the road, the Highlander is celebrated for its spaciousness and user-friendly technology. Safety is a significant focus, with Toyota Safety Sense 2.0 as standard, enhancing confidence for family outings. While it may not be the most exciting driving experience, it certainly prioritizes comfort and convenience, making it an attractive choice for families seeking a reliable SUV.
Other model years to consider
- Average price: $35,589.00
- Good/great deal percentage: 63.0%
- User rating: 5 / 5
- Total listings: 184
- Average price: $35,287.00
- Good/great deal percentage: 71.3%
- User rating: 4.67 / 5
- Total listings: 202
- Average price: $34,688.00
- Good/great deal percentage: 68.1%
- User rating: 4.44 / 5
- Total listings: 207
This analysis is based on CarGurus' proprietary market data from April 14, 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 |
| LE AWD | $38,400 |
| Limited FWD | $43,650 |
| 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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