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Used Toyota Highlander for Sale in Chicago, IL

Highlanders for Sale at Dealers

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2015 Toyota Highlander XLE AWD photo
Price Drop
2015 Toyota Highlander XLE AWD • West Allis, WI
Blue • 3.5L V6 Engine
$14,995 • 172.8k miles
•••

#230 2015-2023 Toyota Highlander

CoPilot AI: It’s a “F” Buy

  • $1,000 Price Drop
  • Dealer Rating - 4.6 stars
More details
2015 Toyota Highlander XLE AWD photo
Price Drop
2015 Toyota Highlander XLE AWD • Crown Point, IN
White • 3.5L V6 Engine
$15,500 • 148.9k miles
•••

#134 2015-2023 Toyota Highlander

CoPilot AI: It’s a “C+” Buy

  • $400 Price Drop
  • Fair Price - $4 Below Market
  • CARFAX: One Owner
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
•••

#225 2015-2023 Toyota Highlander

CoPilot AI: It’s a “D-” Buy

  • Includes $168 Premium Upgrades
  • Motivation to Negotiate - Very High
  • Below Average Mileage
More details
2022 Toyota Highlander Hybrid XLE AWD photo
2022 Toyota Highlander Hybrid XLE AWD • Waukesha, WI
Silver • 2.5L I4 Engine
$31,379 • 96.8k miles
•••

#147 2015-2023 Toyota Highlander

CoPilot AI: It’s a “C+” Buy

  • Fair Price - $462 Above Market
  • CARFAX: One Owner
  • Motivation to Negotiate - Increasing
More details
2016 Toyota Highlander Limited AWD photo
Price Drop
2016 Toyota Highlander Limited AWD • Morton Grove, IL
Black • 3.5L V6 Engine
$24,979 • 58.9k miles
•••

#165 2015-2023 Toyota Highlander

CoPilot AI: It’s a “C-” Buy

  • $19 Price Drop
  • CARFAX: One Owner
  • Very Low Mileage
More details
2016 Toyota Highlander XLE AWD photo
2016 Toyota Highlander XLE AWD • West Allis, WI
Gray • 3.5L V6 Engine
$18,999 • 121.8k miles
•••

#183 2015-2023 Toyota Highlander

CoPilot AI: It’s a “D+” Buy

  • CARFAX: One Owner
  • Motivation to Negotiate - Increasing
  • Average Mileage
More details
2018 Toyota Highlander Limited AWD photo
2018 Toyota Highlander Limited AWD • Naperville, IL
White • 3.5L V6 Engine
$24,431 • 94.7k miles
•••

#108 2015-2023 Toyota Highlander

CoPilot AI: It’s a “C+” Buy

  • Fair Price - $697 Below Market
  • Includes $511 Premium Upgrades
  • CARFAX: One Owner
More details
2023 Toyota Highlander Hybrid Bronze Edition AWD photo
2023 Toyota Highlander Hybrid Bronze Edition AWD • Dixon, IL
White • 2.5L I4 Engine
$39,995 • 55.1k miles
•••

#282 2015-2023 Toyota Highlander

CoPilot AI: It’s a “F” Buy

  • Dealer Rating - 4.6 stars
More details
2019 Toyota Highlander XLE AWD photo
2019 Toyota Highlander XLE AWD • Barrington, IL
Silver • 3.5L V6 Engine
$24,912 • 83.3k miles
•••

#116 2015-2023 Toyota Highlander

CoPilot AI: It’s a “C+” Buy

  • Fair Price - $386 Below Market
  • Includes $161 Premium Upgrades
  • CARFAX: One Owner
More details
2016 Toyota Highlander Limited AWD photo
2016 Toyota Highlander Limited AWD • Hodgkins, IL
Silver • 3.5L V6 Engine
$24,997 • 38.2k miles
•••

#34 2015-2023 Toyota Highlander

CoPilot AI: It’s a “B” Buy

  • Good Price - $775 Below Market
  • CARFAX: One Owner
  • Very Low Mileage
More details
2016 Toyota Highlander Limited Platinum AWD photo
2016 Toyota Highlander Limited Platinum AWD • Naperville, IL
Black • 3.5L V6 Engine
$20,900 • 115.7k miles
•••

#142 2015-2023 Toyota Highlander

CoPilot AI: It’s a “C+” Buy

  • Fair Price - $272 Above Market
  • Below Average Mileage
  • Dealer Rating - 4.8 stars
More details
2022 Toyota Highlander LE AWD photo
12
2022 Toyota Highlander LE AWD • Chicago, IL
Red • 3.5L V6 Engine
$28,995 • 56.7k miles
•••

#12 2015-2023 Toyota Highlander

CoPilot AI: It’s a “B+” Buy

  • Great Price - $2,067 Below Market
  • CARFAX: One Owner
  • Average Mileage
More details
2021 Toyota Highlander Limited AWD photo
2021 Toyota Highlander Limited AWD • Brookfield, WI
Black • 3.5L V6 Engine
$27,492 • 115.9k miles
•••

#238 2015-2023 Toyota Highlander

CoPilot AI: It’s a “F” Buy

  • Includes $373 Premium Upgrades
  • CARFAX: One Owner
  • Dealer Rating - 4.7 stars
More details
2022 Toyota Highlander LE FWD photo
2022 Toyota Highlander LE FWD • Schaumburg, IL
White • 3.5L V6 Engine
$29,245 • 59.4k miles
•••

#144 2015-2023 Toyota Highlander

CoPilot AI: It’s a “C+” Buy

  • Fair Price - $353 Above Market
  • Motivation to Negotiate - Very High
  • Average Mileage
More details
2016 Toyota Highlander XLE AWD photo
2016 Toyota Highlander XLE AWD • Bensenville, IL
Silver • 3.5L V6 Engine
$23,000 • 66.3k miles
•••

#215 2015-2023 Toyota Highlander

CoPilot AI: It’s a “D-” Buy

  • Very Low Mileage
  • Dealer Rating - 4.7 stars
More details
2022 Toyota Highlander Platinum AWD photo
2022 Toyota Highlander Platinum AWD • West Allis, WI
Gray • 3.5L V6 Engine
$27,995 • 129.9k miles
•••

#159 2015-2023 Toyota Highlander

CoPilot AI: It’s a “C” Buy

  • Fair Price - $609 Below Market
  • Includes $392 Premium Upgrades
  • CARFAX: One Owner
More details
2020 Toyota Highlander XLE AWD photo
4
Price Drop
2020 Toyota Highlander XLE AWD • Janesville, WI
Gray • 3.5L V6 Engine
$26,900 • 45.1k miles
•••

#4 2015-2023 Toyota Highlander

CoPilot AI: It’s a “B+” Buy

  • $1,000 Price Drop
  • Great Price - $4,257 Below Market
  • Motivation to Negotiate - Very High
More details
2022 Toyota Highlander XLE AWD photo
1
2022 Toyota Highlander XLE AWD • Naperville, IL
Red • 3.5L V6 Engine
$32,500 • 56.4k miles
•••

#1 2015-2023 Toyota Highlander

CoPilot AI: It’s a “B+” Buy

  • Great Price - $6,800 Below Market
  • CARFAX: One Owner
  • 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
•••

#123 2015-2023 Toyota Highlander

CoPilot AI: It’s a “C+” Buy

  • Fair Price - $277 Below Market
  • Includes $123 Premium Upgrades
  • Average Mileage
More details
2022 Toyota Highlander Limited AWD photo
2022 Toyota Highlander Limited AWD • Tinley Park, IL
Gray • 3.5L V6 Engine
$32,990 • 75k miles
•••

#27 2015-2023 Toyota Highlander

CoPilot AI: It’s a “B” Buy

  • Good Price - $1,573 Below Market
  • Includes $1,203 Premium Upgrades
  • CARFAX: One Owner
More details
2023 Toyota Highlander LE FWD photo
Price Drop
2023 Toyota Highlander LE FWD • Oak Park, IL
Gray • 2.4L I4 Engine
$28,495 • 46k miles
•••

#160 2015-2023 Toyota Highlander

CoPilot AI: It’s a “C” Buy

  • $500 Price Drop
  • Fair Price - $346 Below Market
  • Motivation to Negotiate - Increasing
More details
2017 Toyota Highlander Limited FWD photo
2017 Toyota Highlander Limited FWD • Mokena, IL
Gray • 3.5L V6 Engine
$32,985 • 36.8k miles
•••

#227 2015-2023 Toyota Highlander

CoPilot AI: It’s a “D-” Buy

  • CARFAX: One Owner
  • Very Low Mileage
  • Dealer Rating - 4.7 stars
More details
2016 Toyota Highlander Limited AWD photo
2016 Toyota Highlander Limited AWD • Germantown, WI
Black • 3.5L V6 Engine
$23,500 • 80.3k miles
•••

#167 2015-2023 Toyota Highlander

CoPilot AI: It’s a “C-” Buy

  • Motivation to Negotiate - High
  • Very Low Mileage
  • Dealer Rating - 4.2 stars
More details
2023 Toyota Highlander XLE AWD photo
2023 Toyota Highlander XLE AWD • Dixon, IL
Gray • 2.4L I4 Engine
$38,995 • 39.2k miles
•••

#171 2015-2023 Toyota Highlander

CoPilot AI: It’s a “C-” Buy

  • CARFAX: One Owner
  • Below Average Mileage
  • Dealer Rating - 4.6 stars
More details
2022 Toyota Highlander Hybrid Limited AWD photo
Price Drop
2022 Toyota Highlander Hybrid Limited AWD • Downers Grove, IL
Gold • 2.5L I4 Engine
$33,499 • 94k miles
•••

#33 2015-2023 Toyota Highlander

CoPilot AI: It’s a “B” Buy

  • $900 Price Drop
  • Good Price - $1,212 Below Market
  • Includes $714 Premium Upgrades
More details
1-25 of 361 results
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