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Used 2019 Toyota Highlander for Sale in Chicago, IL

Highlanders for Sale at Dealers

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2019 Toyota Highlander Limited AWD photo
Price Drop
2019 Toyota Highlander Limited AWD • Fort Atkinson, WI
Black • 3.5L V6 Engine
$32,878 • 44.4k miles
•••

#72 2018-2020 Toyota Highlander

CoPilot AI: It’s a “D-” Buy

  • $22 Price Drop
  • Very Low Mileage
  • Dealer Rating - 4.7 stars
More details
2019 Toyota Highlander XLE FWD photo
18
2019 Toyota Highlander XLE FWD • Elgin, IL
Red • 3.5L V6 Engine
$19,999 • 114k miles
•••

#18 2018-2020 Toyota Highlander

CoPilot AI: It’s a “B-” Buy

  • Good Price - $1,027 Below Market
  • CARFAX: One Owner
  • Motivation to Negotiate - Very High
More details
2020 Toyota Highlander Platinum AWD photo
2020 Toyota Highlander Platinum AWD • Delafield, WI
Black • 3.5L V6 Engine
$29,997 • 98.7k miles
•••

#61 2018-2020 Toyota Highlander

CoPilot AI: It’s a “C+” Buy

  • Fair Price - $854 Above Market
More details
2019 Toyota Highlander XLE AWD photo
2019 Toyota Highlander XLE AWD • Hodgkins, IL
White • 3.5L V6 Engine
$26,998 • 74.3k miles • Certified
•••

#63 2018-2020 Toyota Highlander

CoPilot AI: It’s a “C-” Buy

  • Includes $164 Premium Upgrades
  • Below Average Mileage
  • Dealer Rating - 4.5 stars
More details
2019 Toyota Highlander Hybrid XLE AWD photo
Price Drop
2019 Toyota Highlander Hybrid XLE AWD • Elmhurst, IL
3.5L V6 Engine
$14,499 • 263k miles
•••

#84 2018-2020 Toyota Highlander

CoPilot AI: It’s a “F” Buy

  • $500 Price Drop
  • Includes $82 Premium Upgrades
  • CARFAX: One Owner
More details
2018 Toyota Highlander Limited AWD photo
7
Price Drop
2018 Toyota Highlander Limited AWD • Waukesha, WI
Brown • 3.5L V6 Engine
$18,000 • 138.6k miles
•••

#7 2018-2020 Toyota Highlander

CoPilot AI: It’s a “B+” Buy

  • $690 Price Drop
  • Great Price - $1,343 Below Market
  • Includes $107 Premium Upgrades
More details
2018 Toyota Highlander LE AWD photo
6
Price Drop
2018 Toyota Highlander LE AWD • Mundelein, IL
White • 3.5L V6 Engine
$16,998 • 124.2k miles
•••

#6 2018-2020 Toyota Highlander

CoPilot AI: It’s a “B+” Buy

  • $397 Price Drop
  • Great Price - $1,383 Below Market
  • Includes $127 Premium Upgrades
More details
2019 Toyota Highlander XLE AWD photo
2019 Toyota Highlander XLE AWD • Elgin, IL
Black • 3.5L V6 Engine
$25,777 • 77k miles
•••

#31 2018-2020 Toyota Highlander

CoPilot AI: It’s a “B-” Buy

  • Fair Price - $327 Above Market
  • Includes $162 Premium Upgrades
  • CARFAX: One Owner
More details
2020 Toyota Highlander Limited AWD photo
Price Drop
2020 Toyota Highlander Limited AWD • Summit, IL
Black • 3.5L V6 Engine
$23,990 • 123.9k miles
•••

#46 2018-2020 Toyota Highlander

CoPilot AI: It’s a “C+” Buy

  • $1,000 Price Drop
  • Fair Price - $53 Below Market
  • CARFAX: One Owner
More details
2018 Toyota Highlander Hybrid Limited AWD photo
2018 Toyota Highlander Hybrid Limited AWD • Palatine, IL
Red • 3.5L V6 Engine
$24,990 • 94.4k miles
•••

#58 2018-2020 Toyota Highlander

CoPilot AI: It’s a “C+” Buy

  • Fair Price - $513 Above Market
  • Below Average Mileage
  • Dealer Rating - 4.5 stars
More details
2018 Toyota Highlander XLE AWD photo
2018 Toyota Highlander XLE AWD • Kenosha, WI
Red • 3.5L V6 Engine
$22,970 • 87.4k miles
•••

#30 2018-2020 Toyota Highlander

CoPilot AI: It’s a “B-” Buy

  • Fair Price - $179 Above Market
  • Includes $139 Premium Upgrades
  • CARFAX: One Owner
More details
2019 Toyota Highlander XLE AWD photo
11
Price Drop
2019 Toyota Highlander XLE AWD • Naperville, IL
White • 3.5L V6 Engine
$25,477 • 65.6k miles
•••

#11 2018-2020 Toyota Highlander

CoPilot AI: It’s a “B” Buy

  • $300 Price Drop
  • Good Price - $1,162 Below Market
  • Includes $169 Premium Upgrades
More details
2018 Toyota Highlander Hybrid Limited Platinum AWD photo
2018 Toyota Highlander Hybrid Limited Platinum AWD • Mundelein, IL
Blue • 3.5L V6 Engine
$19,498 • 146.4k miles
•••

#48 2018-2020 Toyota Highlander

CoPilot AI: It’s a “C+” Buy

  • Fair Price - $92 Above Market
  • Includes $97 Premium Upgrades
  • Motivation to Negotiate - Increasing
More details
2018 Toyota Highlander XLE AWD photo
Price Drop
2018 Toyota Highlander XLE AWD • Antioch, IL
Black • 3.5L V6 Engine
$19,999 • 122.6k miles
•••

#44 2018-2020 Toyota Highlander

CoPilot AI: It’s a “C+” Buy

  • $461 Price Drop
  • Fair Price - $200 Below Market
  • Includes $122 Premium Upgrades
More details
2018 Toyota Highlander XLE AWD photo
5
Price Drop
2018 Toyota Highlander XLE AWD • Downers Grove, IL
White • 3.5L V6 Engine
$20,000 • 110.2k miles
•••

#5 2018-2020 Toyota Highlander

CoPilot AI: It’s a “B+” Buy

  • $250 Price Drop
  • Great Price - $1,506 Below Market
  • Includes $127 Premium Upgrades
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
•••

#69 2018-2020 Toyota Highlander

CoPilot AI: It’s a “D+” Buy

  • Includes $161 Premium Upgrades
  • CARFAX: One Owner
  • Motivation to Negotiate - Increasing
More details
2019 Toyota Highlander Limited AWD photo
16
Price Drop
2019 Toyota Highlander Limited AWD • Mishawaka, IN
Silver • 3.5L V6 Engine
$24,997 • 98.2k miles
•••

#16 2018-2020 Toyota Highlander

CoPilot AI: It’s a “B-” Buy

  • $601 Price Drop
  • Good Price - $1,331 Below Market
  • Includes $550 Premium Upgrades
More details
2018 Toyota Highlander XLE FWD photo
2018 Toyota Highlander XLE FWD • Chicago, IL
Silver • 3.5L V6 Engine
$19,995 • 153k miles
•••

#76 2018-2020 Toyota Highlander

CoPilot AI: It’s a “F” Buy

  • Motivation to Negotiate - High
  • Dealer Rating - 4.0 stars
More details
2019 Toyota Highlander SE AWD photo
9
2019 Toyota Highlander SE AWD • Plainfield, IL
Red • 3.5L V6 Engine
$27,890 • 56.5k miles
•••

#9 2018-2020 Toyota Highlander

CoPilot AI: It’s a “B” Buy

  • Good Price - $1,215 Below Market
  • Includes $636 Premium Upgrades
  • Very Low Mileage
More details
2019 Toyota Highlander XLE AWD photo
2019 Toyota Highlander XLE AWD • East Dundee, IL
Blue • 3.5L V6 Engine
$21,195 • 112.5k miles
•••

#67 2018-2020 Toyota Highlander

CoPilot AI: It’s a “D+” Buy

  • Includes $141 Premium Upgrades
  • Motivation to Negotiate - Very High
  • Dealer Rating - 4.1 stars
More details
2018 Toyota Highlander Limited AWD photo
2018 Toyota Highlander Limited AWD • Hampshire, IL
White • 3.5L V6 Engine
$19,995 • 135k miles
•••

#42 2018-2020 Toyota Highlander

CoPilot AI: It’s a “C+” Buy

  • Fair Price - $234 Below Market
  • Includes $362 Premium Upgrades
  • Dealer Rating - 4.8 stars
More details
2018 Toyota Highlander XLE AWD photo
Price Drop
2018 Toyota Highlander XLE AWD • McHenry, IL
White • 3.5L V6 Engine
$20,995 • 122.8k miles
•••

#53 2018-2020 Toyota Highlander

CoPilot AI: It’s a “C+” Buy

  • $2,000 Price Drop
  • Fair Price - $196 Above Market
  • Includes $461 Premium Upgrades
More details
2020 Toyota Highlander Hybrid XLE AWD photo
15
Price Drop
2020 Toyota Highlander Hybrid XLE AWD • Naperville, IL
Red • 2.5L I4 Engine
$29,652 • 83.2k miles
•••

#15 2018-2020 Toyota Highlander

CoPilot AI: It’s a “B-” Buy

  • $347 Price Drop
  • Good Price - $1,592 Below Market
  • Average Mileage
More details
2018 Toyota Highlander XLE AWD photo
23
2018 Toyota Highlander XLE AWD • Milwaukee, WI
Black • 3.5L V6 Engine
$20,461 • 114k miles
•••

#23 2018-2020 Toyota Highlander

CoPilot AI: It’s a “B-” Buy

  • Good Price - $719 Below Market
  • Includes $126 Premium Upgrades
  • Average Mileage
More details
2019 Toyota Highlander XLE AWD photo
25
Price Drop
2019 Toyota Highlander XLE AWD • Addison, IL
White • 3.5L V6 Engine
$27,950 • 45.3k miles
•••

#25 2018-2020 Toyota Highlander

CoPilot AI: It’s a “B-” Buy

  • $800 Price Drop
  • Fair Price - $568 Below Market
  • Includes $181 Premium Upgrades
More details
1-25 of 105 results
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2019 Toyota Highlander

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