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Used Toyota Highlander for Sale in Chicago, IL

Highlanders for Sale at Dealers

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2023 Toyota Highlander Platinum AWD photo
Price Drop
2023 Toyota Highlander Platinum AWD • Milwaukee, WI
Black • 2.4L I4 Engine
$33,324 • 74.1k miles
•••

#123 2015-2023 Toyota Highlander

CoPilot AI: It’s a “C+” Buy

  • $666 Price Drop
  • Good Price - $1,869 Below Market
  • Motivation to Negotiate - Increasing
More details
2021 Toyota Highlander Hybrid Limited AWD photo
Price Drop
2021 Toyota Highlander Hybrid Limited AWD • Waukesha, WI
Red • 2.5L I4 Engine
$33,998 • 77k miles
•••

#227 2015-2023 Toyota Highlander

CoPilot AI: It’s a “D+” Buy

  • $343 Price Drop
  • CARFAX: One Owner
  • Motivation to Negotiate - Very High
More details
2017 Toyota Highlander XLE AWD photo
2017 Toyota Highlander XLE AWD • Dixon, IL
Green • 3.5L V6 Engine
$23,595 • 98.6k miles
•••

#234 2015-2023 Toyota Highlander

CoPilot AI: It’s a “D-” Buy

  • Includes $134 Premium Upgrades
  • Below Average Mileage
  • Dealer Rating - 4.6 stars
More details
2019 Toyota Highlander Limited AWD photo
2019 Toyota Highlander Limited AWD • Barrington, IL
White • 3.5L V6 Engine
$23,881 • 107.9k miles
•••

#75 2015-2023 Toyota Highlander

CoPilot AI: It’s a “B-” Buy

  • Good Price - $866 Below Market
  • CARFAX: One Owner
  • Dealer Rating - 4.1 stars
More details
2019 Toyota Highlander XLE AWD photo
2019 Toyota Highlander XLE AWD • Des Plaines, IL
Black • 3.5L V6 Engine
$24,895 • 80.2k miles
•••

#158 2015-2023 Toyota Highlander

CoPilot AI: It’s a “C+” Buy

  • Fair Price - $133 Below Market
  • Includes $158 Premium Upgrades
  • Motivation to Negotiate - Increasing
More details
2019 Toyota Highlander XLE AWD photo
Price Drop
2019 Toyota Highlander XLE AWD • East Dundee, IL
Blue • 3.5L V6 Engine
$21,495 • 112.5k miles
•••

#145 2015-2023 Toyota Highlander

CoPilot AI: It’s a “C+” Buy

  • $500 Price Drop
  • Fair Price - $355 Below Market
  • Motivation to Negotiate - Very High
More details
2023 Toyota Highlander XLE AWD photo
2023 Toyota Highlander XLE AWD • Libertyville, IL
Black • 2.4L I4 Engine
$36,525 • 26.5k miles • Certified
•••

#56 2015-2023 Toyota Highlander

CoPilot AI: It’s a “B-” Buy

  • Good Price - $2,305 Below Market
  • Very Low Mileage
  • Dealer Rating - 4.3 stars
More details
2021 Toyota Highlander Hybrid XLE AWD photo
2021 Toyota Highlander Hybrid XLE AWD • Naperville, IL
Black • 2.5L I4 Engine
$33,489 • 54.7k miles
•••

#201 2015-2023 Toyota Highlander

CoPilot AI: It’s a “C-” Buy

  • Below Average Mileage
  • Dealer Rating - 4.6 stars
More details
2023 Toyota Highlander Platinum AWD photo
Price Drop
2023 Toyota Highlander Platinum AWD • Mishawaka, IN
White • 2.4L I4 Engine
$42,465 • 14.8k miles
•••

#43 2015-2023 Toyota Highlander

CoPilot AI: It’s a “B” Buy

  • $501 Price Drop
  • Good Price - $1,765 Below Market
  • CARFAX: One Owner
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
•••

#104 2015-2023 Toyota Highlander

CoPilot AI: It’s a “B-” Buy

  • $900 Price Drop
  • Fair Price - $8 Below Market
  • Includes $689 Premium Upgrades
More details
2021 Toyota Highlander XLE AWD photo
Price Drop
2021 Toyota Highlander XLE AWD • Milwaukee, WI
Black • 3.5L V6 Engine
$28,850 • 93.3k miles
•••

#217 2015-2023 Toyota Highlander

CoPilot AI: It’s a “D+” Buy

  • $346 Price Drop
  • Motivation to Negotiate - Increasing
  • Dealer Rating - 4.3 stars
More details
2020 Toyota Highlander XLE AWD photo
20
Price Drop
2020 Toyota Highlander XLE AWD • Schaumburg, IL
Blue • 3.5L V6 Engine
$24,322 • 101.2k miles
•••

#20 2015-2023 Toyota Highlander

CoPilot AI: It’s a “B+” Buy

  • $1,033 Price Drop
  • Great Price - $2,118 Below Market
  • CARFAX: One Owner
More details
2023 Toyota Highlander LE AWD photo
Price Drop
2023 Toyota Highlander LE AWD • Park Ridge, IL
Red • 2.4L I4 Engine
$34,500 • 32.4k miles • Certified
•••

#87 2015-2023 Toyota Highlander

CoPilot AI: It’s a “B-” Buy

  • $400 Price Drop
  • Fair Price - $589 Below Market
  • CARFAX: One Owner
More details
2021 Toyota Highlander Hybrid Platinum AWD photo
2021 Toyota Highlander Hybrid Platinum AWD • Peru, IL
White • 2.5L I4 Engine
$36,772 • 72k miles
•••

#182 2015-2023 Toyota Highlander

CoPilot AI: It’s a “C+” Buy

  • Fair Price - $425 Above Market
  • CARFAX: One Owner
  • Average Mileage
More details
2018 Toyota Highlander XLE AWD photo
2018 Toyota Highlander XLE AWD • Morton Grove, IL
Gray • 3.5L V6 Engine
$23,526 • 76.9k miles
•••

#82 2015-2023 Toyota Highlander

CoPilot AI: It’s a “B-” Buy

  • Fair Price - $674 Below Market
  • Includes $143 Premium Upgrades
  • Very Low Mileage
More details
2018 Toyota Highlander SE AWD photo
2018 Toyota Highlander SE AWD • Racine, WI
Red • 3.5L V6 Engine
$22,999 • 116.3k miles
•••

#264 2015-2023 Toyota Highlander

CoPilot AI: It’s a “F” Buy

  • Includes $121 Premium Upgrades
  • Average Mileage
  • Dealer Rating - 4.7 stars
More details
2022 Toyota Highlander Platinum AWD photo
2022 Toyota Highlander Platinum AWD • Elmhurst, IL
Red • 3.5L V6 Engine
$41,988 • 52.1k miles • Certified
•••

#272 2015-2023 Toyota Highlander

CoPilot AI: It’s a “F” Buy

  • CARFAX: One Owner
  • Below Average Mileage
  • Dealer Rating - 4.5 stars
More details
2015 Toyota Highlander XLE AWD photo
Price Drop
2015 Toyota Highlander XLE AWD • Chicago, IL
3.5L V6 Engine
$16,690 • 112.3k miles
•••

#31 2015-2023 Toyota Highlander

CoPilot AI: It’s a “B+” Buy

  • $300 Price Drop
  • Great Price - $1,431 Below Market
  • CARFAX: One Owner
More details
2021 Toyota Highlander XLE AWD photo
Price Drop
2021 Toyota Highlander XLE AWD • Libertyville, IL
White • 3.5L V6 Engine
$29,490 • 63.1k miles
•••

#59 2015-2023 Toyota Highlander

CoPilot AI: It’s a “B-” Buy

  • $260 Price Drop
  • Good Price - $1,488 Below Market
  • Motivation to Negotiate - Increasing
More details
2020 Toyota Highlander XLE AWD photo
2020 Toyota Highlander XLE AWD • Waukesha, WI
Blue • 3.5L V6 Engine
$26,998 • 77.9k miles
•••

#62 2015-2023 Toyota Highlander

CoPilot AI: It’s a “B-” Buy

  • Good Price - $1,172 Below Market
  • Average Mileage
  • Dealer Rating - 4.6 stars
More details
2022 Toyota Highlander XLE AWD photo
2022 Toyota Highlander XLE AWD • Milton, WI
Blue • 3.5L V6 Engine
$32,979 • 57.2k miles
•••

#140 2015-2023 Toyota Highlander

CoPilot AI: It’s a “C+” Buy

  • Fair Price - $398 Below Market
  • CARFAX: One Owner
  • Average Mileage
More details
2019 Toyota Highlander XLE AWD photo
2019 Toyota Highlander XLE AWD • Arlington Heights, IL
Gray • 3.5L V6 Engine
$21,995 • 98.6k miles
•••

#61 2015-2023 Toyota Highlander

CoPilot AI: It’s a “B-” Buy

  • Good Price - $1,244 Below Market
  • Includes $147 Premium Upgrades
  • Motivation to Negotiate - Increasing
More details
2018 Toyota Highlander Limited AWD photo
Price Drop
2018 Toyota Highlander Limited AWD • Hoffman Estates, IL
White • 3.5L V6 Engine
$23,399 • 105.1k miles
•••

#155 2015-2023 Toyota Highlander

CoPilot AI: It’s a “C+” Buy

  • $300 Price Drop
  • Fair Price - $182 Below Market
  • Includes $433 Premium Upgrades
More details
2021 Toyota Highlander Hybrid Limited AWD photo
2021 Toyota Highlander Hybrid Limited AWD • Elmhurst, IL
Black • 2.5L I4 Engine
$35,555 • 69.4k miles
•••

#220 2015-2023 Toyota Highlander

CoPilot AI: It’s a “D+” Buy

  • CARFAX: One Owner
  • Average Mileage
  • Dealer Rating - 4.5 stars
More details
2022 Toyota Highlander XLE AWD photo
2022 Toyota Highlander XLE AWD • Tinley Park, IL
Gray • 3.5L V6 Engine
$34,950 • 42.4k miles
•••

#81 2015-2023 Toyota Highlander

CoPilot AI: It’s a “B-” Buy

  • Fair Price - $693 Below Market
  • Includes $545 Premium Upgrades
  • CARFAX: One Owner
More details
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