Used 2021 Toyota Highlander for Sale near Chicago, IL
CarGurus Analysis: 2021 Toyota Highlander
Summary
- With 4,417 currently listed for sale on CarGurus and an average price of $30,215.80, 35.7% 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.
- 79.4% of 2021 Highlander models on CarGurus are accident free.
- The 2021 Toyota Highlander combined spaciousness and comfort with improved standard safety features, making it a strong contender in the competitive three-row SUV market.
Why it stands out
The 2021 Toyota Highlander stood out in the competitive three-row SUV market with its impressive ride quality and spacious interior, making it a comfortable choice for families. It also included advanced safety technology as standard equipment, enhancing its appeal to safety-conscious buyers. While some may have found its styling uninspired and base engine performance modest, the Highlander's strong name recognition and reliability continued to attract consumers.
Other model years to consider
- 2022 Toyota Highlander: This year offers $33,572.41 average price, 36% good/great deals, 4.6/5 user rating, 8.2/10 expert rating, 6,308 listings.
- 2023 Toyota Highlander: This year offers $35,244.49 average price, 35% good/great deals, 4.4/5 user rating, 6,084 listings.
- 2019 Toyota Highlander: This year offers $23,940.47 average price, 36% good/great deals, 4.6/5 user rating, 3,041 listings.
This analysis is based on CarGurus' proprietary market data from December 16, 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.
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.
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
2021 Toyota Highlander FAQs
How much does the 2021 Toyota Highlander cost in Chicago, IL?
The average 2021 Toyota Highlander costs about $29,391.34. The average price has decreased by -8.6% since last year. The 207 for sale near Chicago, IL on CarGurus, range from $19,347 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?
207 out of 207 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 EV battery range).
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 LE FWD in Chicago IL
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Toyota Highlander Platinum AWD
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Toyota Highlander XSE AWD in Chicago IL
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Toyota Highlander XSE FWD
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Toyota Highlander in Chicago IL
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