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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 • Lincolnwood, IL
Blue • 2.5L I4 Engine
$37,373 • 115.8k miles
•••

#278 2015-2023 Toyota Highlander

CoPilot AI: It’s a “F” Buy

  • Includes $1,358 Premium Upgrades
  • CARFAX: One Owner
  • Dealer Rating - 4.3 stars
More details
2021 Toyota Highlander Platinum AWD photo
Price Drop
2021 Toyota Highlander Platinum AWD • Greenfield, WI
Silver • 3.5L V6 Engine
$37,994 • 65.8k miles
•••

#223 2015-2023 Toyota Highlander

CoPilot AI: It’s a “D+” Buy

  • $140 Price Drop
  • CARFAX: One Owner
  • Below Average Mileage
More details
2019 Toyota Highlander XLE AWD photo
2019 Toyota Highlander XLE AWD • Elgin, IL
Red • 3.5L V6 Engine
$28,554 • 65.2k miles
•••

#231 2015-2023 Toyota Highlander

CoPilot AI: It’s a “D-” Buy

  • CARFAX: One Owner
  • Very Low Mileage
  • Dealer Rating - 4.4 stars
More details
2022 Toyota Highlander Hybrid XLE AWD photo
2022 Toyota Highlander Hybrid XLE AWD • Naperville, IL
Silver • 2.5L I4 Engine
$33,995 • 103.2k miles
•••

#307 2015-2023 Toyota Highlander

CoPilot AI: It’s a “F” Buy

  • CARFAX: One Owner
  • Motivation to Negotiate - Increasing
  • Dealer Rating - 4.8 stars
More details
2022 Toyota Highlander XLE AWD photo
2022 Toyota Highlander XLE AWD • Plymouth, IN
Gold • 3.5L V6 Engine
$35,637 • 52.7k miles
•••

#219 2015-2023 Toyota Highlander

CoPilot AI: It’s a “D+” Buy

  • Includes $541 Premium Upgrades
  • Motivation to Negotiate - High
  • Below Average Mileage
More details
2023 Toyota Highlander XLE AWD photo
2023 Toyota Highlander XLE AWD • Calumet City, IL
Black • 2.4L I4 Engine
$40,733 • 10.7k miles
•••

#83 2015-2023 Toyota Highlander

CoPilot AI: It’s a “B-” Buy

  • Fair Price - $517 Below Market
  • CARFAX: One Owner
  • Very Low Mileage
More details
2023 Toyota Highlander XLE AWD photo
2023 Toyota Highlander XLE AWD • Naperville, IL
Black • 2.4L I4 Engine
$32,709 • 129.2k miles
•••

#308 2015-2023 Toyota Highlander

CoPilot AI: It’s a “F” Buy

  • CARFAX: One Owner
  • Dealer Rating - 4.8 stars
More details
2021 Toyota Highlander XLE AWD photo
2021 Toyota Highlander XLE AWD • Glendale Heights, IL
Silver • 3.5L V6 Engine
$29,548 • 77.2k miles
•••

#154 2015-2023 Toyota Highlander

CoPilot AI: It’s a “C+” Buy

  • Fair Price - $114 Below Market
  • Motivation to Negotiate - Increasing
  • Average Mileage
More details
2016 Toyota Highlander XLE AWD photo
2016 Toyota Highlander XLE AWD • Racine, WI
White • 3.5L V6 Engine
$18,995 • 160.1k miles
•••

#269 2015-2023 Toyota Highlander

CoPilot AI: It’s a “F” Buy

  • CARFAX: One Owner
  • Dealer Rating - 4.7 stars
More details
2022 Toyota Highlander XLE AWD photo
2022 Toyota Highlander XLE AWD • McHenry, IL
Gold • 3.5L V6 Engine
$38,250 • 28.7k miles
•••

#235 2015-2023 Toyota Highlander

CoPilot AI: It’s a “D-” Buy

  • CARFAX: One Owner
  • Very Low Mileage
  • Dealer Rating - 5.0 stars
More details
2019 Toyota Highlander Limited Platinum AWD photo
Price Drop
2019 Toyota Highlander Limited Platinum AWD • Dixon, IL
Silver • 3.5L V6 Engine
$30,515 • 75.6k miles
•••

#201 2015-2023 Toyota Highlander

CoPilot AI: It’s a “C-” Buy

  • $2,080 Price Drop
  • Includes $408 Premium Upgrades
  • CARFAX: One Owner
More details
2019 Toyota Highlander XLE AWD photo
23
Price Drop
2019 Toyota Highlander XLE AWD • Merrillville, IN
Black • 3.5L V6 Engine
$21,950 • 114.3k miles
•••

#23 2015-2023 Toyota Highlander

CoPilot AI: It’s a “B+” Buy

  • $250 Price Drop
  • Great Price - $1,566 Below Market
  • Includes $148 Premium Upgrades
More details
2022 Toyota Highlander XLE AWD photo
Price Drop
2022 Toyota Highlander XLE AWD • Milwaukee, WI
Gray • 3.5L V6 Engine
$31,901 • 81.8k miles
•••

#185 2015-2023 Toyota Highlander

CoPilot AI: It’s a “C+” Buy

  • $536 Price Drop
  • Fair Price - $738 Above Market
  • Includes $496 Premium Upgrades
More details
2023 Toyota Highlander L FWD photo
Price Drop
2023 Toyota Highlander L FWD • Delavan, WI
2.4L I4 Engine
$33,218 • 70.7k miles
•••

#276 2015-2023 Toyota Highlander

CoPilot AI: It’s a “F” Buy

  • $1,360 Price Drop
  • CARFAX: One Owner
  • Motivation to Negotiate - Very High
More details
2018 Toyota Highlander SE AWD photo
2018 Toyota Highlander SE AWD • Ottawa, IL
Red • 3.5L V6 Engine
$17,986 • 149.2k miles
•••

#33 2015-2023 Toyota Highlander

CoPilot AI: It’s a “B+” Buy

  • Great Price - $1,157 Below Market
  • Motivation to Negotiate - Increasing
  • Dealer Rating - 4.2 stars
More details
2022 Toyota Highlander Hybrid Platinum AWD photo
2022 Toyota Highlander Hybrid Platinum AWD • Milwaukee, WI
Blue • 2.5L I4 Engine
$42,463 • 57.6k miles
•••

#145 2015-2023 Toyota Highlander

CoPilot AI: It’s a “C+” Buy

  • Fair Price - $270 Below Market
  • Includes $559 Premium Upgrades
  • CARFAX: One Owner
More details
2017 Toyota Highlander SE AWD photo
Price Drop
2017 Toyota Highlander SE AWD • Naperville, IL
Gray • 3.5L V6 Engine
$16,990 • 151.1k miles
•••

#31 2015-2023 Toyota Highlander

CoPilot AI: It’s a “B+” Buy

  • $400 Price Drop
  • Great Price - $1,222 Below Market
  • CARFAX: One Owner
More details
2023 Toyota Highlander Hybrid XLE AWD photo
Price Drop
2023 Toyota Highlander Hybrid XLE AWD • Valparaiso, IN
Red • 2.5L I4 Engine
$37,528 • 66.2k miles
•••

#174 2015-2023 Toyota Highlander

CoPilot AI: It’s a “C+” Buy

  • $371 Price Drop
  • Fair Price - $368 Above Market
  • Includes $595 Premium Upgrades
More details
2023 Toyota Highlander Platinum AWD photo
2023 Toyota Highlander Platinum AWD • Schaumburg, IL
White • 2.4L I4 Engine
$40,168 • 66.9k miles
•••

#193 2015-2023 Toyota Highlander

CoPilot AI: It’s a “C” Buy

  • Fair Price - $957 Above Market
  • Dealer Rating - 4.4 stars
More details
2021 Toyota Highlander L AWD photo
Price Drop
2021 Toyota Highlander L AWD • Palatine, IL
Gray • 3.5L V6 Engine
$26,911 • 65.8k miles
•••

#179 2015-2023 Toyota Highlander

CoPilot AI: It’s a “C+” Buy

  • $895 Price Drop
  • Fair Price - $521 Above Market
  • Motivation to Negotiate - Increasing
More details
2019 Toyota Highlander Limited Platinum AWD photo
2019 Toyota Highlander Limited Platinum AWD • Naperville, IL
Black • 3.5L V6 Engine
$25,595 • 113.7k miles
•••

#140 2015-2023 Toyota Highlander

CoPilot AI: It’s a “C+” Buy

  • Fair Price - $341 Below Market
  • Includes $142 Premium Upgrades
  • CARFAX: One Owner
More details
2021 Toyota Highlander Hybrid XLE AWD photo
Price Drop
2021 Toyota Highlander Hybrid XLE AWD • Arlington Heights, IL
Black • 2.5L I4 Engine
$22,495 • 166.7k miles
•••

#120 2015-2023 Toyota Highlander

CoPilot AI: It’s a “C+” Buy

  • $500 Price Drop
  • Good Price - $830 Below Market
  • Motivation to Negotiate - Increasing
More details
2018 Toyota Highlander XLE AWD photo
2018 Toyota Highlander XLE AWD • Lansing, IL
Red • 3.5L V6 Engine
$18,212 • 131.1k miles
•••

#32 2015-2023 Toyota Highlander

CoPilot AI: It’s a “B+” Buy

  • Great Price - $1,184 Below Market
  • Includes $369 Premium Upgrades
  • CARFAX: One Owner
More details
2019 Toyota Highlander LE AWD photo
2019 Toyota Highlander LE AWD • Benton Harbor, MI
White • 3.5L V6 Engine
$22,990 • 104.5k miles
•••

#265 2015-2023 Toyota Highlander

CoPilot AI: It’s a “F” Buy

  • Motivation to Negotiate - Increasing
  • Dealer Rating - 4.2 stars
More details
2016 Toyota Highlander XLE AWD photo
18
Price Drop
2016 Toyota Highlander XLE AWD • Bensenville, IL
Black • 3.5L V6 Engine
$18,495 • 93.5k miles
•••

#18 2015-2023 Toyota Highlander

CoPilot AI: It’s a “B+” Buy

  • $1,502 Price Drop
  • Great Price - $1,981 Below Market
  • Motivation to Negotiate - Increasing
More details
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2026 Toyota Highlander

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