Used 2021 Toyota Highlander for Sale near Chicago, IL
CarGurus Analysis: 2021 Toyota Highlander
Summary
- With 4,592 currently listed for sale on CarGurus and an average price of $30,564.30, 34.6% of 2021 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
- Favorably reviewed: Owners rated the 2021 Toyota Highlander 4.8 / 5 stars and CarGurus experts gave it an 7.5 / 10.
- 80.2% of 2021 Highlander models on CarGurus are accident free.
- The 2021 Toyota Highlander provided a comfortable and spacious ride, bolstered by an array of standard safety features, though it faced some competition due to its uninspired styling and base engine performance.
Why it stands out
The 2021 Toyota Highlander stood out in the competitive three-row SUV market due to its exceptional ride quality and spacious interior, making it a comfortable choice for families. It also led the way in safety by incorporating additional technology as standard equipment, enhancing its appeal to safety-conscious buyers. While its styling and base engine received mixed reviews, the overall design offered a reliable and practical option for those seeking a versatile vehicle.
Other model years to consider
- 2022 Toyota Highlander: This year offers $33,925.22 average price, 34% good/great deals, 4.6/5 user rating, 8.2/10 expert rating, 6,414 listings.
- 2023 Toyota Highlander: This year offers $35,595.40 average price, 34% good/great deals, 4.4/5 user rating, 6,158 listings.
- 2019 Toyota Highlander: This year offers $24,132.82 average price, 37% good/great deals, 4.6/5 user rating, 3,154 listings.
This analysis is based on CarGurus' proprietary market data from December 3, 2025, CarGurus experts' opinions, and generative AI.
4.9 Overall rating
(44 reviews)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.
Toyota knocked it out of the park again with this 2021 Highlander Platinum. Luxurious quiet ride Lexus feel like. Very happy with this purchase.
I tried the 2023 Platinum Highlander and I was really disappointed in the engine performance! Thats why I stepped back to a 2021 Platinum, for the bigger, more powerful 6-cyl! With all other items being equal, I would definitely be more inclined to purchase a 21 or 22 Platinum with the 3.5L 6cyl engine. Excellent vehicle! We currently have a 2010 with 150+K miles and its been an excellent vehicle, its just time to get my wife a newer car!
Great ride. Fantastic features, its loaded. Gets very good gas mileage. Dont hear outside noises. Love the sun roof & powered lift gate. Its lacking nothing!
Drives great and has all the tech you need. I have a limited V6.
2021 Toyota Highlander FAQs
How much does the 2021 Toyota Highlander cost in Chicago, IL?
The average 2021 Toyota Highlander costs about $30,485.61. The average price has decreased by -7.8% since last year. The 294 for sale near Chicago, IL on CarGurus, range from $20,128 to $48,902 in price.
Is the 2021 Toyota Highlander a good car?
CarGurus experts gave the 2021 Toyota Highlander an overall rating of 7.5/10 and 2021 Toyota Highlander owners have rated the vehicle a 4.8/5 stars on average. If a vehicle has both strong expert and owner reviews, you can feel confident in its quality. If either expert reviews, owner reviews, or both are spotty, you might want to do some research to figure out where the car falls short.
How many 2021 Toyota Highlander vehicles in Chicago, IL have no reported accidents or damage?
294 out of 294 for sale near Chicago, IL have no reported accidents or damage.
Is the 2021 Toyota Highlander safe?
CarGurus experts gave the 2021 Toyota Highlander a safety rating of 10/10.
What is the fuel economy of the 2021 Toyota Highlander?
Depending on the engine and options, the 2021 Toyota Highlander gets between 23 and 23 MPG (or MPGe).
What fuel types are available?
Gasoline engines are available.
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Toyota Highlander XLE AWD in Chicago IL
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Toyota Highlander XLE FWD
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Toyota Highlander Limited AWD in Chicago IL
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Toyota Highlander XSE AWD in Chicago IL
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Toyota Highlander Platinum AWD
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Toyota Highlander L FWD
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Toyota Highlander Limited FWD
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Toyota Highlander XSE FWD
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Toyota Highlander in Chicago IL
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