Used cars/Toyota Grand Highlander/Chicago

Used Toyota Grand Highlander in Chicago

74 used Toyota Grand Highlander are for sale at 36 dealers within 40 miles of downtown Chicago. The median price is $43,815 at 36,821 mi.

74For sale
$43,815Median price
36,821 miMedian mileage
18%Under market
36Dealers

Ranked among 72 used Toyota Grand Highlander

Best used Grand Highlander deals in Chicago

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Great deal #1 of 13

$52,998 $4,071 under market (7.1%) 2026 Toyota Grand Highlander Limited 4,885 mi · Used · Ruby Flare Pearl Market price $57,069 · Score 76/100 At AutoNation Hyundai O'Hare

Good deal #2 of 32

$44,903 $2,239 under market (4.8%) 2024 Toyota Grand Highlander Limited 23,030 mi · Used · Celestial Silver Metallic Market price $47,142 · Score 68/100 At Chicago Northside Toyota

Good deal #2 of 13

$56,427 $2,301 under market (3.9%) 2026 Toyota Grand Highlander Platinum 5,000 mi · Used · Pearl Market price $58,728 · Score 66/100 At Zeigler Chrysler Dodge Jeep Ram of Downers Grove

Good deal #2 of 27

$41,603 $2,725 under market (6.1%) 2025 Toyota Grand Highlander XLE 29,779 mi · Used · Celestial Silver Metallic Market price $44,328 · Score 65/100 At Elgin Toyota

Good deal #4 of 13

$47,304 $2,698 under market (5.4%) 2026 Toyota Grand Highlander XLE 17,891 mi · Used · Storm Cloud Market price $50,002 · Score 63/100 At Zeigler Chrysler Dodge Jeep Ram of Downers Grove

Good deal #6 of 13

$48,376 $2,111 under market (4.2%) 2026 Toyota Grand Highlander XLE 12,925 mi · Used · Midnight Black Market price $50,487 · Score 60/100 At AutoNation Hyundai O'Hare

Deals against the market

About 7% under market

The best-ranked used Toyota Grand Highlander in Chicago this week is at AutoNation Hyundai O'Hare. 18% of the 72 ranked cars here are advertised under market.

How a used car is ranked

Market price comes from every used Toyota Grand 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 years with at least 3 cars for sale. Advertised price is the dealer's own figure, before tax, title and registration. 8 of the 74 are certified pre-owned.
Model year	For sale	Median price	Median mileage
2026 Toyota Grand Highlander	14	$55,897	12,925 mi
2025 Toyota Grand Highlander	27	$43,373	42,426 mi
2024 Toyota Grand Highlander	33	$41,299	37,908 mi

Dealers with the most used Grand Highlander

All Chicago dealers

Quick answers

How many used Toyota Grand Highlander are for sale in Chicago?

74 used Toyota Grand Highlander, model years 2024 to 2026, are advertised by 36 dealers within 40 miles of downtown Chicago, as of November 13, 2026. 8 are certified pre-owned.

What does a used Toyota Grand Highlander cost in Chicago?

The median advertised price for a used Toyota Grand Highlander in Chicago is $43,815, from 73 advertised prices ranging from $27,843 to $61,666. Median mileage is 36,821 mi. Prices are before tax, title and registration.

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

The best-ranked used Toyota Grand Highlander in Chicago this week is at AutoNation Hyundai O'Hare, about 7% under market for its age and mileage. 18% of the 72 ranked cars are advertised at least 3% under market.

Which Chicago dealers have the most used Toyota Grand Highlander?

Elgin Toyota in Streamwood (7), Oakbrook Toyota in Westmont in Westmont (6), Zeigler Chrysler Dodge Jeep Ram of Downers Grove in Downers Grove (5).

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 November 6, 2026 and November 13, 2026.