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Used 2019 Toyota Highlander for Sale in Chicago, IL

Highlanders for Sale at Dealers

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Trim
2018 Toyota Highlander SE AWD photo
2018 Toyota Highlander SE AWD • Hinsdale, IL
Red • 3.5L V6 Engine
$26,999 • 58.8k miles
•••

#31 2018-2020 Toyota Highlander

CoPilot AI: It’s a “B-” Buy

  • Fair Price - $369 Above Market
  • Includes $493 Premium Upgrades
  • Motivation to Negotiate - Increasing
More details
2019 Toyota Highlander Limited AWD photo
2019 Toyota Highlander Limited AWD • Tinley Park, IL
White • 3.5L V6 Engine
$31,999 • 74.8k miles
•••

#74 2018-2020 Toyota Highlander

CoPilot AI: It’s a “D-” Buy

  • Includes $169 Premium Upgrades
  • Motivation to Negotiate - Very High
  • Below Average Mileage
More details
2019 Toyota Highlander XLE AWD photo
Price Drop
2019 Toyota Highlander XLE AWD • Elgin, IL
3.5L V6 Engine
$26,000 • 80.9k miles
•••

#59 2018-2020 Toyota Highlander

CoPilot AI: It’s a “C+” Buy

  • Fair Price - $634 Above Market
  • CARFAX: One Owner
  • Below Average Mileage
More details
2018 Toyota Highlander XLE AWD photo
2018 Toyota Highlander XLE AWD • Milwaukee, WI
Silver • 3.5L V6 Engine
$19,995 • 116.8k miles
•••

#38 2018-2020 Toyota Highlander

CoPilot AI: It’s a “C+” Buy

  • Fair Price - $450 Below Market
  • Includes $124 Premium Upgrades
  • Motivation to Negotiate - Increasing
More details
2018 Toyota Highlander LE Plus AWD photo
20
Price Drop
2018 Toyota Highlander LE Plus AWD • Morton Grove, IL
White • 3.5L V6 Engine
$21,410 • 88.9k miles
•••

#20 2018-2020 Toyota Highlander

CoPilot AI: It’s a “B-” Buy

  • $1 Price Drop
  • Fair Price - $597 Below Market
  • Motivation to Negotiate - Increasing
More details
2019 Toyota Highlander SE AWD photo
22
2019 Toyota Highlander SE AWD • Mishawaka, IN
White • 3.5L V6 Engine
$26,499 • 79k miles
•••

#22 2018-2020 Toyota Highlander

CoPilot AI: It’s a “B-” Buy

  • Fair Price - $439 Below Market
  • Includes $164 Premium Upgrades
  • Below Average Mileage
More details
2018 Toyota Highlander Limited AWD photo
Price Drop
2018 Toyota Highlander Limited AWD • Greenfield, WI
3.5L V6 Engine
$25,384 • 92.6k miles
•••

#70 2018-2020 Toyota Highlander

CoPilot AI: It’s a “D+” Buy

  • $107 Price Drop
  • Motivation to Negotiate - Increasing
  • Below Average Mileage
More details
2019 Toyota Highlander Limited AWD photo
Price Drop
2019 Toyota Highlander Limited AWD • Milwaukee, WI
White • 3.5L V6 Engine
$29,364 • 71.6k miles
•••

#29 2018-2020 Toyota Highlander

CoPilot AI: It’s a “B-” Buy

  • $183 Price Drop
  • Fair Price - $260 Above Market
  • Includes $171 Premium Upgrades
More details
2019 Toyota Highlander XLE AWD photo
Price Drop
2019 Toyota Highlander XLE AWD • DeKalb, IL
Gray • 3.5L V6 Engine
$23,488 • 110.8k miles • Certified
•••

#47 2018-2020 Toyota Highlander

CoPilot AI: It’s a “C+” Buy

  • $1,500 Price Drop
  • Fair Price - $11 Above Market
  • Includes $149 Premium Upgrades
More details
2018 Toyota Highlander XLE AWD photo
16
2018 Toyota Highlander XLE AWD • Lansing, IL
Red • 3.5L V6 Engine
$18,500 • 131.1k miles
•••

#16 2018-2020 Toyota Highlander

CoPilot AI: It’s a “B-” Buy

  • Good Price - $1,042 Below Market
  • Includes $372 Premium Upgrades
  • CARFAX: One Owner
More details
2018 Toyota Highlander SE AWD photo
18
2018 Toyota Highlander SE AWD • Ottawa, IL
Red • 3.5L V6 Engine
$17,986 • 149.2k miles
•••

#18 2018-2020 Toyota Highlander

CoPilot AI: It’s a “B-” Buy

  • Good Price - $651 Below Market
  • Motivation to Negotiate - Increasing
  • Dealer Rating - 4.2 stars
More details
2020 Toyota Highlander Limited AWD photo
13
Price Drop
2020 Toyota Highlander Limited AWD • St. Charles, IL
Silver • 3.5L V6 Engine
$28,500 • 74.4k miles
•••

#13 2018-2020 Toyota Highlander

CoPilot AI: It’s a “B-” Buy

  • $500 Price Drop
  • Good Price - $1,617 Below Market
  • CARFAX: One Owner
More details
2019 Toyota Highlander XLE AWD photo
17
Price Drop
2019 Toyota Highlander XLE AWD • Lemont, IL
Gray • 3.5L V6 Engine
$26,400 • 71.7k miles
•••

#17 2018-2020 Toyota Highlander

CoPilot AI: It’s a “B-” Buy

  • $500 Price Drop
  • Fair Price - $790 Below Market
  • Includes $551 Premium Upgrades
More details
2018 Toyota Highlander XLE FWD photo
10
2018 Toyota Highlander XLE FWD • Michigan City, IN
White • 3.5L V6 Engine
$18,995 • 135.6k miles
•••

#10 2018-2020 Toyota Highlander

CoPilot AI: It’s a “B+” Buy

  • Great Price - $1,302 Below Market
  • Motivation to Negotiate - Very High
  • Dealer Rating - 4.4 stars
More details
2019 Toyota Highlander Hybrid Limited Platinum AWD photo
12
Price Drop
2019 Toyota Highlander Hybrid Limited Platinum AWD • DeKalb, IL
White • 3.5L V6 Engine
$23,898 • 115.6k miles
•••

#12 2018-2020 Toyota Highlander

CoPilot AI: It’s a “B” Buy

  • $90 Price Drop
  • Good Price - $843 Below Market
  • Includes $750 Premium Upgrades
More details
2019 Toyota Highlander XLE AWD photo
2
Price Drop
2019 Toyota Highlander XLE AWD • Lincolnwood, IL
Gray • 3.5L V6 Engine
$15,363 • 155.3k miles
•••

#2 2018-2020 Toyota Highlander

CoPilot AI: It’s a “B+” Buy

  • $10 Price Drop
  • Great Price - $4,199 Below Market
  • Includes $125 Premium Upgrades
More details
2018 Toyota Highlander LE Plus AWD photo
2018 Toyota Highlander LE Plus AWD • Princeton, IL
White • 3.5L V6 Engine
$17,999 • 157.2k miles
•••

#65 2018-2020 Toyota Highlander

CoPilot AI: It’s a “D+” Buy

  • Dealer Rating - 5.0 stars
More details
2020 Toyota Highlander XLE FWD photo
2020 Toyota Highlander XLE FWD • Oak Forest, IL
Silver • 3.5L V6 Engine
$25,980 • 83.1k miles
•••

#43 2018-2020 Toyota Highlander

CoPilot AI: It’s a “C+” Buy

  • Fair Price - $178 Below Market
  • Average Mileage
  • Dealer Rating - 4.5 stars
More details
2018 Toyota Highlander XLE AWD photo
19
Price Drop
2018 Toyota Highlander XLE AWD • Naperville, IL
Red • 3.5L V6 Engine
$22,810 • 86.3k miles
•••

#19 2018-2020 Toyota Highlander

CoPilot AI: It’s a “B-” Buy

  • $180 Price Drop
  • Fair Price - $635 Below Market
  • Includes $140 Premium Upgrades
More details
2020 Toyota Highlander XLE FWD photo
Price Drop
2020 Toyota Highlander XLE FWD • Morton Grove, IL
Black • 3.5L V6 Engine
$27,201 • 80.3k miles
•••

#56 2018-2020 Toyota Highlander

CoPilot AI: It’s a “C+” Buy

  • $110 Price Drop
  • Fair Price - $460 Above Market
  • Motivation to Negotiate - Increasing
More details
2019 Toyota Highlander XLE AWD photo
Price Drop
2019 Toyota Highlander XLE AWD • Chicago, IL
Red • 3.5L V6 Engine
$24,984 • 87.9k miles
•••

#36 2018-2020 Toyota Highlander

CoPilot AI: It’s a “C+” Buy

  • $856 Price Drop
  • Fair Price - $539 Below Market
  • Includes $162 Premium Upgrades
More details
2020 Toyota Highlander Hybrid XLE AWD photo
Price Drop
2020 Toyota Highlander Hybrid XLE AWD • Janesville, WI
Blue • 2.5L I4 Engine
$27,127 • 125.7k miles
•••

#80 2018-2020 Toyota Highlander

CoPilot AI: It’s a “F” Buy

  • $500 Price Drop
  • Motivation to Negotiate - Very High
  • Dealer Rating - 4.3 stars
More details
2019 Toyota Highlander XLE AWD photo
6
2019 Toyota Highlander XLE AWD • Dwight, IL
Black • 3.5L V6 Engine
$20,900 • 112.4k miles
•••

#6 2018-2020 Toyota Highlander

CoPilot AI: It’s a “B+” Buy

  • Great Price - $2,105 Below Market
  • Includes $454 Premium Upgrades
  • CARFAX: One Owner
More details
2018 Toyota Highlander Limited Platinum AWD photo
2018 Toyota Highlander Limited Platinum AWD • Michigan City, IN
White • 3.5L V6 Engine
$22,977 • 132.4k miles
•••

#68 2018-2020 Toyota Highlander

CoPilot AI: It’s a “D+” Buy

  • Includes $358 Premium Upgrades
  • CARFAX: One Owner
  • Dealer Rating - 4.6 stars
More details
2020 Toyota Highlander Limited AWD photo
2020 Toyota Highlander Limited AWD • Ottawa, IL
3.5L V6 Engine
$29,597 • 84.8k miles
•••

#62 2018-2020 Toyota Highlander

CoPilot AI: It’s a “C-” Buy

  • Includes $642 Premium Upgrades
  • CARFAX: One Owner
  • Average Mileage
More details
1-25 of 106 results
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2019 Toyota Highlander

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