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Used 2016 Toyota Highlander for Sale in Chicago, IL

Highlanders for Sale at Dealers

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2018 Toyota Highlander XLE FWD photo
Price Drop
2018 Toyota Highlander XLE FWD • Chicago, IL
Silver • 3.5L V6 Engine
$17,237 • 153k miles
•••

Not Ranked

CoPilot AI: It’s a “B” Buy

  • $2,758 Price Drop
  • Fair Price - $242 Above Market
  • Motivation to Negotiate - Very High
More details
2017 Toyota Highlander XLE AWD photo
New Find
2017 Toyota Highlander XLE AWD • Chicago, IL
White • 3.5L V6 Engine
$17,599 • 169.1k miles
•••

Not Ranked

CoPilot AI: It’s a “C” Buy

  • Dealer Rating - 4.3 stars
More details
2015 Toyota Highlander LE FWD photo
2015 Toyota Highlander LE FWD • Chicago, IL
Black • 2.7L I4 Engine
$13,995 • 177.1k miles
•••

Not Ranked

CoPilot AI: It’s a “D” Buy

  • Motivation to Negotiate - Very High
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2016 Toyota Highlander LE Plus AWD photo
Price Drop
New Find
2016 Toyota Highlander LE Plus AWD • Evergreen Park, IL
Gray • 3.5L V6 Engine
$18,992 • 118.8k miles
•••

Not Ranked

CoPilot AI: It’s a “B” Buy

  • $353 Price Drop
  • Fair Price - $183 Below Market
  • CARFAX: One Owner
More details
2017 Toyota Highlander Hybrid Limited Platinum AWD photo
Price Drop
2017 Toyota Highlander Hybrid Limited Platinum AWD • Oak Lawn, IL
Silver • 3.5L V6 Engine
$29,294 • 78.2k miles
•••

Not Ranked

CoPilot AI: It’s a “B+” Buy

  • $459 Price Drop
  • Fair Price - $317 Above Market
  • Motivation to Negotiate - Very High
More details
2018 Toyota Highlander Limited AWD photo
New Find
2018 Toyota Highlander Limited AWD • Oak Lawn, IL
White • 3.5L V6 Engine
$26,963 • 75.6k miles
•••

Not Ranked

CoPilot AI: It’s a “B+” Buy

  • Fair Price - $765 Below Market
  • Includes $567 Premium Upgrades
  • CARFAX: One Owner
More details
2017 Toyota Highlander XLE AWD photo
Price Drop
2017 Toyota Highlander XLE AWD • Chicago, IL
Gray • 3.5L V6 Engine
$22,484 • 100.3k miles
•••

Not Ranked

CoPilot AI: It’s a “B” Buy

  • $35 Price Drop
  • Fair Price - $496 Above Market
  • Includes $136 Premium Upgrades
More details
2017 Toyota Highlander XLE AWD photo
Price Drop
New Find
2017 Toyota Highlander XLE AWD • Burbank, IL
Silver • 3.5L V6 Engine
$17,995 • 127.5k miles
•••

Not Ranked

CoPilot AI: It’s an “A” Buy

  • $1,000 Price Drop
  • Great Price - $1,830 Below Market
  • Average Mileage
More details
2018 Toyota Highlander Limited AWD photo
New Find
2018 Toyota Highlander Limited AWD • Chicago, IL
Black • 3.5L V6 Engine
$27,128 • 80.2k miles
•••

Not Ranked

CoPilot AI: It’s a “B+” Buy

  • Fair Price - $747 Above Market
  • Includes $146 Premium Upgrades
  • Very Low Mileage
More details
2015 Toyota Highlander Limited Platinum AWD photo
Price Drop
2015 Toyota Highlander Limited Platinum AWD • Hodgkins, IL
White • 3.5L V6 Engine
$20,648 • 94.9k miles
•••

Not Ranked

CoPilot AI: It’s an “A-” Buy

  • $500 Price Drop
  • Good Price - $863 Below Market
  • Motivation to Negotiate - Increasing
More details
2019 Toyota Highlander XLE AWD photo
New Find
2019 Toyota Highlander XLE AWD • Alsip, IL
White • 3.5L V6 Engine
$19,277 • 149.6k miles
•••

Not Ranked

CoPilot AI: It’s an “A” Buy

  • Great Price - $1,930 Below Market
  • Includes $469 Premium Upgrades
  • CARFAX: One Owner
More details
2019 Toyota Highlander Hybrid XLE AWD photo
New Find
2019 Toyota Highlander Hybrid XLE AWD • Palos Hills, IL
Green • 3.5L V6 Engine
$26,995 • 108k miles
•••

Not Ranked

CoPilot AI: It’s a “C” Buy

  • Includes $157 Premium Upgrades
  • CARFAX: One Owner
  • Dealer Rating - 4.5 stars
More details
2016 Toyota Highlander XLE AWD photo
New Find
2016 Toyota Highlander XLE AWD • Palos Hills, IL
Green • 3.5L V6 Engine
$16,699 • 133.5k miles
•••

Not Ranked

CoPilot AI: It’s a “B+” Buy

  • Great Price - $1,886 Below Market
  • Includes $129 Premium Upgrades
  • Average Mileage
More details
2015 Toyota Highlander LE Plus FWD photo
2015 Toyota Highlander LE Plus FWD • Chicago, IL
Silver • 3.5L V6 Engine
$11,900 • 228.7k miles
•••

Not Ranked

CoPilot AI: It’s a “D” Buy

  • Dealer Rating - 4.1 stars
More details
2015 Toyota Highlander XLE AWD photo
New Find
2015 Toyota Highlander XLE AWD • Crestwood, IL
Gray • 3.5L V6 Engine
$14,622 • 170.8k miles
•••

Not Ranked

CoPilot AI: It’s a “B” Buy

  • Fair Price - $245 Below Market
  • Dealer Rating - 4.6 stars
More details
2019 Toyota Highlander SE AWD photo
Price Drop
2019 Toyota Highlander SE AWD • Crestwood, IL
Red • 3.5L V6 Engine
$18,408 • 156.4k miles
•••

Not Ranked

CoPilot AI: It’s a “B-” Buy

  • $587 Price Drop
  • Fair Price - $489 Below Market
  • Includes $116 Premium Upgrades
More details
2018 Toyota Highlander Limited Platinum AWD photo
New Find
2018 Toyota Highlander Limited Platinum AWD • Westmont, IL
White • 3.5L V6 Engine
$23,993 • 113.5k miles
•••

Not Ranked

CoPilot AI: It’s a “B” Buy

  • Fair Price - $80 Above Market
  • Includes $123 Premium Upgrades
  • CARFAX: One Owner
More details
2017 Toyota Highlander XLE AWD photo
Price Drop
2017 Toyota Highlander XLE AWD • Clarendon Hills, IL
Silver • 3.5L V6 Engine
$17,680 • 139.5k miles
•••

Not Ranked

CoPilot AI: It’s an “A+” Buy

  • $221 Price Drop
  • Great Price - $2,285 Below Market
  • Includes $975 Premium Upgrades
More details
2015 Toyota Highlander XLE AWD photo
New Find
2015 Toyota Highlander XLE AWD • Willowbrook, IL
Gray • 3.5L V6 Engine
$18,199 • 120.1k miles
•••

Not Ranked

CoPilot AI: It’s a “B” Buy

  • Fair Price - $46 Below Market
  • Below Average Mileage
More details
2019 Toyota Highlander XLE AWD photo
Price Drop
2019 Toyota Highlander XLE AWD • Bensenville, IL
Brown • 3.5L V6 Engine
$21,495 • 116.7k miles
•••

Not Ranked

CoPilot AI: It’s an “A” Buy

  • $500 Price Drop
  • Great Price - $2,107 Below Market
  • Includes $148 Premium Upgrades
More details
2019 Toyota Highlander LE AWD photo
Price Drop
2019 Toyota Highlander LE AWD • Elmhurst, IL
Gray • 3.5L V6 Engine
$21,666 • 92.7k miles • Certified
•••

Not Ranked

CoPilot AI: It’s a “C” Buy

  • $494 Price Drop
  • Average Mileage
  • Dealer Rating - 4.5 stars
More details
2019 Toyota Highlander XLE AWD photo
2019 Toyota Highlander XLE AWD • Elmhurst, IL
Red • 3.5L V6 Engine
$23,838 • 103k miles
•••

Not Ranked

CoPilot AI: It’s a “B” Buy

  • Fair Price - $660 Below Market
  • Includes $154 Premium Upgrades
  • Average Mileage
More details
2017 Toyota Highlander XLE AWD photo
New Find
2017 Toyota Highlander XLE AWD • Park Ridge, IL
Black • 3.5L V6 Engine
$25,900 • 66.4k miles
•••

Not Ranked

CoPilot AI: It’s a “D+” Buy

  • CARFAX: One Owner
  • Very Low Mileage
More details
2019 Toyota Highlander XLE AWD photo
Price Drop
2019 Toyota Highlander XLE AWD • Des Plaines, IL
Blue • 3.5L V6 Engine
$20,376 • 123.4k miles
•••

Not Ranked

CoPilot AI: It’s an “A” Buy

  • $652 Price Drop
  • Great Price - $2,316 Below Market
  • Includes $144 Premium Upgrades
More details
2018 Toyota Highlander XLE AWD photo
Price Drop
2018 Toyota Highlander XLE AWD • Oak Forest, IL
Gray • 3.5L V6 Engine
$21,357 • 87.7k miles
•••

Not Ranked

CoPilot AI: It’s an “A+” Buy

  • $1,000 Price Drop
  • Great Price - $2,839 Below Market
  • Includes $145 Premium Upgrades
More details
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2016 Toyota Highlander

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