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Used cars/Toyota Highlander/Chicago

Used Toyota Highlander in Chicago

193 used Toyota Highlander are for sale at 92 dealers within 40 miles of downtown Chicago. The median price is $31,282 at 60,513 mi.

Ranked among 174 used Toyota Highlander

Best used Highlander deals in Chicago

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Deals against the market

About 15% under market

The best-ranked used Toyota Highlander in Chicago this week is at AutoNation Hyundai O'Hare. 26% of the 174 ranked cars here are advertised under market.

How a used car is ranked

Market price comes from every used Toyota Highlander in Chicago: what price does at each year of age and each mile, then adjusted for trim, color and certified status. The score adds mileage for the car's age and whether the listing has photos. How we rank.

Prices by model year

Model yearFor saleMedian priceMedian mileage
2026 Toyota Highlander 18 $52,201 1,375 mi
2025 Toyota Highlander 13 $42,871 31,874 mi
2024 Toyota Highlander 27 $40,811 34,055 mi
2023 Toyota Highlander 24 $33,829 56,075 mi
2022 Toyota Highlander 23 $31,978 60,333 mi
2021 Toyota Highlander 15 $31,654 65,641 mi
2020 Toyota Highlander 4 Too few to state Too few to state
2019 Toyota Highlander 15 $26,612 81,565 mi
2018 Toyota Highlander 10 $24,431 89,816 mi
2017 Toyota Highlander 18 $23,151 94,178 mi
2016 Toyota Highlander 5 Too few to state Too few to state
2015 Toyota Highlander 8 $17,535 127,141 mi
2013 Toyota Highlander 4 Too few to state Too few to state
2012 Toyota Highlander 3 Too few to state Too few to state
Model years with at least 3 cars for sale. Advertised price is the dealer's own figure, before tax, title and registration. 9 of the 193 are certified pre-owned.

Dealers with the most used Highlander

All Chicago dealers

Quick answers

How many used Toyota Highlander are for sale in Chicago?

193 used Toyota Highlander, model years 2005 to 2026, are advertised by 92 dealers within 40 miles of downtown Chicago, as of November 13, 2026. 9 are certified pre-owned.

What does a used Toyota Highlander cost in Chicago?

The median advertised price for a used Toyota Highlander in Chicago is $31,282, from 180 advertised prices ranging from $8,185 to $57,866. Median mileage is 60,513 mi. Prices are before tax, title and registration.

Where is the best deal on a used Toyota Highlander in Chicago?

The best-ranked used Toyota Highlander in Chicago this week is at AutoNation Hyundai O'Hare, about 15% under market for its age and mileage. 26% of the 174 ranked cars are advertised at least 3% under market.

Which Chicago dealers have the most used Toyota Highlander?

Zeigler Chrysler Dodge Jeep Ram of Downers Grove in Downers Grove (12), Elgin Toyota in Streamwood (12), Continental Toyota in Hodgkins (7).

Carfinity reads each dealer's public website. A car listed on more than one site is counted once. Dealer sites in this summary were last read between October 17, 2026 and November 13, 2026.

Used Highlander in other markets

Other used models in Chicago