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Used Toyota Highlander for Sale in Chicago, IL

Highlanders for Sale at Dealers

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2023 Toyota Highlander Hybrid Limited AWD photo
2023 Toyota Highlander Hybrid Limited AWD • Ottawa, IL
Gray • 2.5L I4 Engine
$36,997 • 86.3k miles
•••

#169 2015-2023 Toyota Highlander

CoPilot AI: It’s a “C” Buy

  • Fair Price - $354 Above Market
  • Includes $615 Premium Upgrades
  • CARFAX: One Owner
More details
2022 Toyota Highlander Hybrid XLE AWD photo
Price Drop
2022 Toyota Highlander Hybrid XLE AWD • Palatine, IL
2.5L I4 Engine
$31,400 • 80.5k miles
•••

#111 2015-2023 Toyota Highlander

CoPilot AI: It’s a “C+” Buy

  • $90 Price Drop
  • Fair Price - $727 Below Market
  • CARFAX: One Owner
More details
2019 Toyota Highlander Hybrid XLE AWD photo
24
2019 Toyota Highlander Hybrid XLE AWD • Highland, IN
Gray • 3.5L V6 Engine
$21,800 • 129.4k miles
•••

#24 2015-2023 Toyota Highlander

CoPilot AI: It’s a “B+” Buy

  • Great Price - $1,510 Below Market
  • Includes $789 Premium Upgrades
  • CARFAX: One Owner
More details
2022 Toyota Highlander Hybrid XLE AWD photo
Price Drop
2022 Toyota Highlander Hybrid XLE AWD • Waukesha, WI
Silver • 2.5L I4 Engine
$31,259 • 96.8k miles
•••

#197 2015-2023 Toyota Highlander

CoPilot AI: It’s a “D+” Buy

  • $320 Price Drop
  • CARFAX: One Owner
  • Motivation to Negotiate - Increasing
More details
2022 Toyota Highlander XLE AWD photo
17
2022 Toyota Highlander XLE AWD • Calumet City, IL
White • 3.5L V6 Engine
$34,903 • 33.9k miles
•••

#17 2015-2023 Toyota Highlander

CoPilot AI: It’s a “B+” Buy

  • Great Price - $2,365 Below Market
  • Includes $1,391 Premium Upgrades
  • CARFAX: One Owner
More details
2018 Toyota Highlander XLE AWD photo
2018 Toyota Highlander XLE AWD • Milwaukee, WI
Black • 3.5L V6 Engine
$20,461 • 114k miles
•••

#65 2015-2023 Toyota Highlander

CoPilot AI: It’s a “B-” Buy

  • Good Price - $762 Below Market
  • Includes $127 Premium Upgrades
  • Average Mileage
More details
2019 Toyota Highlander XLE AWD photo
2019 Toyota Highlander XLE AWD • Milwaukee, WI
White • 3.5L V6 Engine
$26,698 • 75k miles
•••

#174 2015-2023 Toyota Highlander

CoPilot AI: It’s a “C-” Buy

  • Includes $163 Premium Upgrades
  • Below Average Mileage
  • Dealer Rating - 4.4 stars
More details
2023 Toyota Highlander Hybrid Limited AWD photo
2023 Toyota Highlander Hybrid Limited AWD • Tinley Park, IL
Black • 2.5L I4 Engine
$41,999 • 43.1k miles
•••

#53 2015-2023 Toyota Highlander

CoPilot AI: It’s a “B-” Buy

  • Good Price - $1,969 Below Market
  • Includes $607 Premium Upgrades
  • CARFAX: One Owner
More details
2018 Toyota Highlander Limited Platinum AWD photo
2018 Toyota Highlander Limited Platinum AWD • Germantown, WI
Black • 3.5L V6 Engine
$25,995 • 92.8k miles
•••

#177 2015-2023 Toyota Highlander

CoPilot AI: It’s a “C-” Buy

  • Includes $658 Premium Upgrades
  • CARFAX: One Owner
  • Motivation to Negotiate - Increasing
More details
2021 Toyota Highlander Hybrid LE FWD photo
Price Drop
2021 Toyota Highlander Hybrid LE FWD • Hodgkins, IL
Black • 2.5L I4 Engine
$28,574 • 83k miles
•••

#202 2015-2023 Toyota Highlander

CoPilot AI: It’s a “D+” Buy

  • $424 Price Drop
  • CARFAX: One Owner
  • Motivation to Negotiate - Increasing
More details
2019 Toyota Highlander XLE AWD photo
13
Price Drop
2019 Toyota Highlander XLE AWD • Arlington Heights, IL
Gray • 3.5L V6 Engine
$20,995 • 98.6k miles
•••

#13 2015-2023 Toyota Highlander

CoPilot AI: It’s a “B+” Buy

  • $500 Price Drop
  • Great Price - $2,683 Below Market
  • Includes $150 Premium Upgrades
More details
2015 Toyota Highlander Limited AWD photo
Price Drop
2015 Toyota Highlander Limited AWD • Plainfield, IL
Blue • 3.5L V6 Engine
$17,485 • 117.7k miles
•••

#33 2015-2023 Toyota Highlander

CoPilot AI: It’s a “B+” Buy

  • $507 Price Drop
  • Great Price - $1,117 Below Market
  • CARFAX: One Owner
More details
2016 Toyota Highlander Limited AWD photo
2016 Toyota Highlander Limited AWD • Milwaukee, WI
White • 3.5L V6 Engine
$17,997 • 148.6k miles
•••

#193 2015-2023 Toyota Highlander

CoPilot AI: It’s a “D+” Buy

  • CARFAX: One Owner
  • Dealer Rating - 4.2 stars
More details
2021 Toyota Highlander Hybrid Limited AWD photo
Price Drop
2021 Toyota Highlander Hybrid Limited AWD • Milwaukee, WI
Gray • 2.5L I4 Engine
$29,332 • 106.5k miles
•••

#140 2015-2023 Toyota Highlander

CoPilot AI: It’s a “C+” Buy

  • $188 Price Drop
  • Fair Price - $94 Above Market
  • Includes $414 Premium Upgrades
More details
2017 Toyota Highlander Limited AWD photo
2017 Toyota Highlander Limited AWD • Elgin, IL
White • 3.5L V6 Engine
$19,999 • 145.3k miles
•••

#228 2015-2023 Toyota Highlander

CoPilot AI: It’s a “F” Buy

  • Dealer Rating - 4.4 stars
More details
2023 Toyota Highlander XSE AWD photo
Price Drop
2023 Toyota Highlander XSE AWD • Milwaukee, WI
Gray • 2.4L I4 Engine
$40,853 • 27.2k miles
•••

#171 2015-2023 Toyota Highlander

CoPilot AI: It’s a “C” Buy

  • $609 Price Drop
  • Includes $1,100 Premium Upgrades
  • CARFAX: One Owner
More details
2022 Toyota Highlander XSE AWD photo
2022 Toyota Highlander XSE AWD • Shorewood, IL
Black • 3.5L V6 Engine
$34,294 • 64.9k miles
•••

#162 2015-2023 Toyota Highlander

CoPilot AI: It’s a “C+” Buy

  • Fair Price - $610 Above Market
  • CARFAX: One Owner
  • Average Mileage
More details
2021 Toyota Highlander XLE AWD photo
Price Drop
2021 Toyota Highlander XLE AWD • Milwaukee, WI
Black • 3.5L V6 Engine
$27,947 • 93.3k miles
•••

#151 2015-2023 Toyota Highlander

CoPilot AI: It’s a “C+” Buy

  • $301 Price Drop
  • Fair Price - $274 Above Market
  • Motivation to Negotiate - Increasing
More details
2021 Toyota Highlander XSE AWD photo
2021 Toyota Highlander XSE AWD • Downers Grove, IL
White • 3.5L V6 Engine
$38,888 • 40.7k miles
•••

#224 2015-2023 Toyota Highlander

CoPilot AI: It’s a “D-” Buy

  • Includes $524 Premium Upgrades
  • Very Low Mileage
  • Dealer Rating - 4.1 stars
More details
2020 Toyota Highlander XLE AWD photo
2020 Toyota Highlander XLE AWD • Westmont, IL
Black • 3.5L V6 Engine
$30,999 • 65.7k miles
•••

#216 2015-2023 Toyota Highlander

CoPilot AI: It’s a “D-” Buy

  • CARFAX: One Owner
  • Below Average Mileage
  • Dealer Rating - 4.6 stars
More details
2023 Toyota Highlander XLE AWD photo
Price Drop
2023 Toyota Highlander XLE AWD • Libertyville, IL
Gray • 2.4L I4 Engine
$35,861 • 40.7k miles
•••

#114 2015-2023 Toyota Highlander

CoPilot AI: It’s a “C+” Buy

  • $169 Price Drop
  • Fair Price - $577 Below Market
  • CARFAX: One Owner
More details
2023 Toyota Highlander Hybrid XLE AWD photo
Price Drop
2023 Toyota Highlander Hybrid XLE AWD • Mt Pleasant, WI
White • 2.5L I4 Engine
$28,749 • 127.5k miles
•••

#172 2015-2023 Toyota Highlander

CoPilot AI: It’s a “C-” Buy

  • $2,241 Price Drop
  • Fair Price - $617 Above Market
  • Dealer Rating - 4.6 stars
More details
2019 Toyota Highlander Limited AWD photo
2019 Toyota Highlander Limited AWD • Carol Stream, IL
White • 3.5L V6 Engine
$28,995 • 84.3k miles
•••

#205 2015-2023 Toyota Highlander

CoPilot AI: It’s a “D+” Buy

  • Includes $162 Premium Upgrades
  • CARFAX: One Owner
  • Motivation to Negotiate - Increasing
More details
2023 Toyota Highlander L FWD photo
Price Drop
2023 Toyota Highlander L FWD • West Allis, WI
Gray • 2.4L I4 Engine
$32,955 • 11.3k miles
•••

#87 2015-2023 Toyota Highlander

CoPilot AI: It’s a “B-” Buy

  • $955 Price Drop
  • Fair Price - $137 Below Market
  • CARFAX: One Owner
More details
2023 Toyota Highlander Hybrid Limited AWD photo
2023 Toyota Highlander Hybrid Limited AWD • Dixon, IL
White • 2.5L I4 Engine
$43,888 • 24k miles
•••

#88 2015-2023 Toyota Highlander

CoPilot AI: It’s a “B-” Buy

  • Fair Price - $114 Below Market
  • CARFAX: One Owner
  • Very Low Mileage
More details
1-25 of 347 results
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