CoPilot AI-Assisted Car Shopping

 New Search
 Save
 Sort
 Share

Used 2019 Toyota Highlander for Sale in Chicago, IL

Highlanders for Sale at Dealers

Filters
Price
Year
Mileage
Trim
2020 Toyota Highlander XLE AWD photo
2020 Toyota Highlander XLE AWD • Milwaukee, WI
Blue • 3.5L V6 Engine
$32,995 • 36.1k miles
•••

#36 2018-2020 Toyota Highlander

CoPilot AI: It’s a “B-” Buy

  • Fair Price - $736 Above Market
  • Motivation to Negotiate - Increasing
  • Very Low Mileage
More details
2019 Toyota Highlander SE AWD photo
Price Drop
2019 Toyota Highlander SE AWD • Oak Forest, IL
Black • 3.5L V6 Engine
$22,600 • 122.5k miles
•••

#53 2018-2020 Toyota Highlander

CoPilot AI: It’s a “C+” Buy

  • $300 Price Drop
  • Fair Price - $65 Above Market
  • Includes $493 Premium Upgrades
More details
2020 Toyota Highlander XLE FWD photo
17
2020 Toyota Highlander XLE FWD • Barrington, IL
Black • 3.5L V6 Engine
$30,744 • 36.1k miles
•••

#17 2018-2020 Toyota Highlander

CoPilot AI: It’s a “B” Buy

  • Fair Price - $139 Above Market
  • Includes $870 Premium Upgrades
  • Motivation to Negotiate - Very High
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
•••

#50 2018-2020 Toyota Highlander

CoPilot AI: It’s a “C+” Buy

  • $2,000 Price Drop
  • Fair Price - $27 Above Market
  • Includes $465 Premium Upgrades
More details
2018 Toyota Highlander XLE AWD photo
2018 Toyota Highlander XLE AWD • Morton Grove, IL
Black • 3.5L V6 Engine
$22,999 • 88k miles
•••

#30 2018-2020 Toyota Highlander

CoPilot AI: It’s a “B-” Buy

  • Fair Price - $295 Below Market
  • Includes $139 Premium Upgrades
  • CARFAX: One Owner
More details
2018 Toyota Highlander Limited FWD photo
Price Drop
2018 Toyota Highlander Limited FWD • Naperville, IL
3.5L V6 Engine
$26,495 • 58.7k miles
•••

#32 2018-2020 Toyota Highlander

CoPilot AI: It’s a “B-” Buy

  • $100 Price Drop
  • Fair Price - $68 Above Market
  • Includes $134 Premium Upgrades
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
•••

#55 2018-2020 Toyota Highlander

CoPilot AI: It’s a “C+” Buy

  • $300 Price Drop
  • Fair Price - $264 Above Market
  • Includes $424 Premium Upgrades
More details
2018 Toyota Highlander Limited AWD photo
Price Drop
2018 Toyota Highlander Limited AWD • Crystal Lake, IL
Green • 3.5L V6 Engine
$19,998 • 151.2k miles
•••

#78 2018-2020 Toyota Highlander

CoPilot AI: It’s a “F” Buy

  • $1 Price Drop
  • Motivation to Negotiate - Very High
  • Dealer Rating - 4.4 stars
More details
2020 Toyota Highlander XLE AWD photo
7
Price Drop
2020 Toyota Highlander XLE AWD • Janesville, WI
Gray • 3.5L V6 Engine
$27,900 • 45.1k miles
•••

#7 2018-2020 Toyota Highlander

CoPilot AI: It’s a “B+” Buy

  • $1,000 Price Drop
  • Great Price - $2,613 Below Market
  • Motivation to Negotiate - Very High
More details
2019 Toyota Highlander Hybrid Limited AWD photo
Price Drop
2019 Toyota Highlander Hybrid Limited AWD • Libertyville, IL
White • 3.5L V6 Engine
$25,479 • 97.5k miles
•••

#39 2018-2020 Toyota Highlander

CoPilot AI: It’s a “C+” Buy

  • $1,011 Price Drop
  • Fair Price - $587 Below Market
  • Includes $521 Premium Upgrades
More details
2018 Toyota Highlander Limited AWD photo
2018 Toyota Highlander Limited AWD • Naperville, IL
Black • 3.5L V6 Engine
$23,995 • 95.7k miles
•••

#65 2018-2020 Toyota Highlander

CoPilot AI: It’s a “D+” Buy

  • Includes $129 Premium Upgrades
  • CARFAX: One Owner
  • Below Average Mileage
More details
2019 Toyota Highlander Limited Platinum AWD photo
20
Price Drop
2019 Toyota Highlander Limited Platinum AWD • Villa Park, IL
Silver • 3.5L V6 Engine
$24,555 • 97.1k miles
•••

#20 2018-2020 Toyota Highlander

CoPilot AI: It’s a “B-” Buy

  • $60 Price Drop
  • Good Price - $1,286 Below Market
  • Includes $458 Premium Upgrades
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
•••

#61 2018-2020 Toyota Highlander

CoPilot AI: It’s a “C” Buy

  • $500 Price Drop
  • Fair Price - $102 Below Market
  • Includes $90 Premium Upgrades
More details
2019 Toyota Highlander LE Plus FWD photo
Price Drop
2019 Toyota Highlander LE Plus FWD • Waukegan, IL
Silver • 3.5L V6 Engine
$18,499 • 125.4k miles
•••

#45 2018-2020 Toyota Highlander

CoPilot AI: It’s a “C+” Buy

  • $500 Price Drop
  • Fair Price - $429 Below Market
  • Motivation to Negotiate - Very High
More details
2019 Toyota Highlander XLE AWD photo
15
2019 Toyota Highlander XLE AWD • Elmhurst, IL
Gray • 3.5L V6 Engine
$24,163 • 76k miles
•••

#15 2018-2020 Toyota Highlander

CoPilot AI: It’s a “B” Buy

  • Good Price - $1,134 Below Market
  • Includes $579 Premium Upgrades
  • Motivation to Negotiate - Very High
More details
2020 Toyota Highlander Limited AWD photo
16
Price Drop
2020 Toyota Highlander Limited AWD • Libertyville, IL
Gray • 3.5L V6 Engine
$29,920 • 56.6k miles
•••

#16 2018-2020 Toyota Highlander

CoPilot AI: It’s a “B” Buy

  • $431 Price Drop
  • Fair Price - $802 Below Market
  • Includes $659 Premium Upgrades
More details
2019 Toyota Highlander XLE AWD photo
5
2019 Toyota Highlander XLE AWD • Lincolnwood, IL
Gray • 3.5L V6 Engine
$15,373 • 155.3k miles
•••

#5 2018-2020 Toyota Highlander

CoPilot AI: It’s a “B+” Buy

  • Great Price - $2,689 Below Market
  • Includes $116 Premium Upgrades
  • Motivation to Negotiate - High
More details
2019 Toyota Highlander XLE AWD photo
Price Drop
2019 Toyota Highlander XLE AWD • Cary, IL
Black • 3.5L V6 Engine
$17,999 • 157.5k miles
•••

#60 2018-2020 Toyota Highlander

CoPilot AI: It’s a “C” Buy

  • $500 Price Drop
  • Fair Price - $106 Below Market
  • Includes $114 Premium Upgrades
More details
2018 Toyota Highlander XLE FWD photo
2018 Toyota Highlander XLE FWD • Chicago, IL
Silver • 3.5L V6 Engine
$17,995 • 153k miles
•••

#57 2018-2020 Toyota Highlander

CoPilot AI: It’s a “C+” Buy

  • Fair Price - $502 Above Market
  • Motivation to Negotiate - Increasing
  • Dealer Rating - 4.0 stars
More details
2020 Toyota Highlander XLE AWD photo
Price Drop
2020 Toyota Highlander XLE AWD • Schaumburg, IL
Blue • 3.5L V6 Engine
$25,955 • 101.2k miles
•••

#44 2018-2020 Toyota Highlander

CoPilot AI: It’s a “C+” Buy

  • $1 Price Drop
  • Fair Price - $466 Below Market
  • CARFAX: One Owner
More details
2019 Toyota Highlander LE Plus AWD photo
2019 Toyota Highlander LE Plus AWD • West Allis, WI
Green • 3.5L V6 Engine
$21,995 • 97.8k miles
•••

#42 2018-2020 Toyota Highlander

CoPilot AI: It’s a “C+” Buy

  • Fair Price - $492 Below Market
  • Includes $485 Premium Upgrades
  • Average Mileage
More details
2020 Toyota Highlander Hybrid XLE AWD photo
14
2020 Toyota Highlander Hybrid XLE AWD • McHenry, IL
Gray • 2.5L I4 Engine
$36,999 • 32.2k miles
•••

#14 2018-2020 Toyota Highlander

CoPilot AI: It’s a “B” Buy

  • Good Price - $2,013 Below Market
  • CARFAX: One Owner
  • Very Low Mileage
More details
2020 Toyota Highlander XLE AWD photo
18
Price Drop
2020 Toyota Highlander XLE AWD • Gurnee, IL
Black • 3.5L V6 Engine
$27,499 • 72.6k miles
•••

#18 2018-2020 Toyota Highlander

CoPilot AI: It’s a “B-” Buy

  • $396 Price Drop
  • Good Price - $1,349 Below Market
  • CARFAX: One Owner
More details
2018 Toyota Highlander Hybrid Limited AWD photo
2018 Toyota Highlander Hybrid Limited AWD • Brookfield, WI
Red • 3.5L V6 Engine
$19,992 • 143.7k miles
•••

#54 2018-2020 Toyota Highlander

CoPilot AI: It’s a “C+” Buy

  • Fair Price - $113 Above Market
  • CARFAX: One Owner
  • Dealer Rating - 4.6 stars
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
•••

#37 2018-2020 Toyota Highlander

CoPilot AI: It’s a “C+” Buy

  • $1,000 Price Drop
  • Fair Price - $736 Below Market
  • CARFAX: One Owner
More details
1-25 of 108 results
HomeToyotaHighlander

2019 Toyota Highlander

Mid-size Crossover
Seats
8
Fuel Economy
20City MPG
24Hwy MPG
NHTSA Rating Summary
Copilot Rating
Dimensions
Most Popular Models like Highlander
Other Years
Research More Models
View more SUVs

© 2026 CoPilot. All Rights Reserved.