CoPilot AI-Assisted Car Shopping

 New Search
 Save
 Sort
 Share

Used 2018 Toyota Highlander for Sale in Chicago, IL

Highlanders for Sale at Dealers

Filters
Price
Year
Mileage
Trim
2018 Toyota Highlander XLE AWD photo
Price Drop
2018 Toyota Highlander XLE AWD Mequon, WI
Black 3.5L V6 Engine
$17,490 153.1k miles
•••

#44 2017-2019 Toyota Highlander

CoPilot AI: It’s aC+” Buy

  • $500 Price Drop
  • Fair Price - $245 Below Market
  • Includes $107 Premium Upgrades
More details
2019 Toyota Highlander XLE AWD photo
2019 Toyota Highlander XLE AWD Palatine, IL
Green 3.5L V6 Engine
$20,999 136.1k miles
•••

#77 2017-2019 Toyota Highlander

CoPilot AI: It’s aF” Buy

  • CARFAX: One Owner
  • Motivation to Negotiate - Increasing
  • Dealer Rating - 4.4 stars
More details
2019 Toyota Highlander XLE AWD photo
2019 Toyota Highlander XLE AWD Waukesha, WI
Red 3.5L V6 Engine
$26,725 66.4k miles
•••

#33 2017-2019 Toyota Highlander

CoPilot AI: It’s aB-” Buy

  • Fair Price - $443 Above Market
  • Includes $166 Premium Upgrades
  • CARFAX: One Owner
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
•••

#38 2017-2019 Toyota Highlander

CoPilot AI: It’s aC+” Buy

  • $500 Price Drop
  • Good Price - $471 Below Market
  • Includes $92 Premium Upgrades
More details
2017 Toyota Highlander Limited AWD photo
23
2017 Toyota Highlander Limited AWD Algonquin, IL
Black 3.5L V6 Engine
$19,999 116.4k miles
•••

#23 2017-2019 Toyota Highlander

CoPilot AI: It’s aB-” Buy

  • Good Price - $966 Below Market
  • CARFAX: One Owner
  • Average Mileage
More details
2019 Toyota Highlander XLE AWD photo
22
Price Drop
2019 Toyota Highlander XLE AWD Crystal Lake, IL
Gray 3.5L V6 Engine
$20,790 115k miles
•••

#22 2017-2019 Toyota Highlander

CoPilot AI: It’s aB-” Buy

  • $9 Price Drop
  • Good Price - $1,016 Below Market
  • Includes $138 Premium Upgrades
More details
2018 Toyota Highlander SE AWD photo
2018 Toyota Highlander SE AWD Elkhart, IN
White 3.5L V6 Engine
$21,348 123.3k miles
•••

#69 2017-2019 Toyota Highlander

CoPilot AI: It’s aD+” Buy

  • Includes $116 Premium Upgrades
  • Dealer Rating - 4.6 stars
More details
2019 Toyota Highlander XLE FWD photo
Price Drop
2019 Toyota Highlander XLE FWD Elgin, IL
Red 3.5L V6 Engine
$19,999 114k miles
•••

#30 2017-2019 Toyota Highlander

CoPilot AI: It’s aB-” Buy

  • $1,000 Price Drop
  • Fair Price - $397 Below Market
  • Includes $675 Premium Upgrades
More details
2019 Toyota Highlander XLE AWD photo
11
Price Drop
2019 Toyota Highlander XLE AWD East Dundee, IL
Gray 3.5L V6 Engine
$23,925 76k miles
•••

#11 2017-2019 Toyota Highlander

CoPilot AI: It’s aB” Buy

  • $25 Price Drop
  • Good Price - $1,330 Below Market
  • Includes $578 Premium Upgrades
More details
2019 Toyota Highlander LE AWD photo
Price Drop
2019 Toyota Highlander LE AWD Granger, IN
Gray 3.5L V6 Engine
$15,308 163.3k miles
•••

#55 2017-2019 Toyota Highlander

CoPilot AI: It’s aC” Buy

  • $1,142 Price Drop
  • Fair Price - $255 Below Market
  • Includes $116 Premium Upgrades
More details
2019 Toyota Highlander Limited AWD photo
2
Price Drop
2019 Toyota Highlander Limited AWD Libertyville, IL
Red 3.5L V6 Engine
$25,946 72.2k miles
•••

#2 2017-2019 Toyota Highlander

CoPilot AI: It’s aB+” Buy

  • $95 Price Drop
  • Great Price - $5,148 Below Market
  • Includes $164 Premium Upgrades
More details
2018 Toyota Highlander XLE AWD photo
19
2018 Toyota Highlander XLE AWD Waukesha, WI
Silver 3.5L V6 Engine
$20,350 113.3k miles
•••

#19 2017-2019 Toyota Highlander

CoPilot AI: It’s aB-” Buy

  • Good Price - $1,149 Below Market
  • Includes $127 Premium Upgrades
  • CARFAX: One Owner
More details
2017 Toyota Highlander LE FWD photo
2017 Toyota Highlander LE FWD Schaumburg, IL
Green 2.7L I4 Engine
$18,998 105.8k miles
•••

#78 2017-2019 Toyota Highlander

CoPilot AI: It’s aF” Buy

  • Includes $142 Premium Upgrades
  • Below Average Mileage
  • Dealer Rating - 4.3 stars
More details
2019 Toyota Highlander XLE AWD photo
18
Price Drop
2019 Toyota Highlander XLE AWD Forest Park, IL
Silver 3.5L V6 Engine
$21,233 109.4k miles
•••

#18 2017-2019 Toyota Highlander

CoPilot AI: It’s aB-” Buy

  • $551 Price Drop
  • Good Price - $1,175 Below Market
  • Includes $142 Premium Upgrades
More details
2018 Toyota Highlander LE AWD photo
Price Drop
2018 Toyota Highlander LE AWD Mundelein, IL
White 3.5L V6 Engine
$17,395 124.2k miles
•••

#41 2017-2019 Toyota Highlander

CoPilot AI: It’s aC+” Buy

  • $600 Price Drop
  • Fair Price - $356 Below Market
  • Includes $122 Premium Upgrades
More details
2018 Toyota Highlander Limited Platinum AWD photo
2018 Toyota Highlander Limited Platinum AWD Germantown, WI
Black 3.5L V6 Engine
$25,995 92.8k miles
•••

#57 2017-2019 Toyota Highlander

CoPilot AI: It’s aC-” Buy

  • Includes $658 Premium Upgrades
  • CARFAX: One Owner
  • Below Average Mileage
More details
2017 Toyota Highlander Hybrid Limited Platinum AWD photo
Price Drop
2017 Toyota Highlander Hybrid Limited Platinum AWD Schererville, IN
Black 3.5L V6 Engine
$17,262 170.8k miles
•••

#37 2017-2019 Toyota Highlander

CoPilot AI: It’s aC+” Buy

  • $268 Price Drop
  • Fair Price - $511 Below Market
  • CARFAX: One Owner
More details
2017 Toyota Highlander SE AWD photo
2017 Toyota Highlander SE AWD Milwaukee, WI
Black 3.5L V6 Engine
$24,258 77.4k miles
•••

#72 2017-2019 Toyota Highlander

CoPilot AI: It’s aD-” Buy

  • CARFAX: One Owner
  • Very Low Mileage
  • Dealer Rating - 4.2 stars
More details
2017 Toyota Highlander Limited AWD photo
Price Drop
2017 Toyota Highlander Limited AWD Greenfield, WI
Silver 3.5L V6 Engine
$19,768 127k miles
•••

#26 2017-2019 Toyota Highlander

CoPilot AI: It’s aB-” Buy

  • $385 Price Drop
  • Good Price - $851 Below Market
  • Includes $116 Premium Upgrades
More details
2019 Toyota Highlander Limited AWD photo
9
2019 Toyota Highlander Limited AWD Rolling Meadows, IL
Gray 3.5L V6 Engine
$27,900 49.7k miles
•••

#9 2017-2019 Toyota Highlander

CoPilot AI: It’s aB+” Buy

  • Great Price - $1,802 Below Market
  • Includes $176 Premium Upgrades
  • Very Low Mileage
More details
2019 Toyota Highlander Limited AWD photo
17
Price Drop
2019 Toyota Highlander Limited AWD Libertyville, IL
Red 3.5L V6 Engine
$25,495 82.4k miles Certified
•••

#17 2017-2019 Toyota Highlander

CoPilot AI: It’s aB-” Buy

  • $1,000 Price Drop
  • Good Price - $1,321 Below Market
  • Includes $158 Premium Upgrades
More details
2017 Toyota Highlander XLE AWD photo
2017 Toyota Highlander XLE AWD Schaumburg, IL
White 3.5L V6 Engine
$33,997 22.6k miles
•••

#75 2017-2019 Toyota Highlander

CoPilot AI: It’s aD-” Buy

  • Motivation to Negotiate - Increasing
  • Very Low Mileage
  • Dealer Rating - 4.9 stars
More details
2019 Toyota Highlander Hybrid Limited Platinum AWD photo
13
Price Drop
2019 Toyota Highlander Hybrid Limited Platinum AWD St. Charles, IL
White 3.5L V6 Engine
$27,896 72.2k miles
•••

#13 2017-2019 Toyota Highlander

CoPilot AI: It’s aB” Buy

  • $399 Price Drop
  • Good Price - $1,292 Below Market
  • CARFAX: One Owner
More details
2019 Toyota Highlander XLE AWD photo
2019 Toyota Highlander XLE AWD West Allis, WI
White 3.5L V6 Engine
$21,995 113.8k miles
•••

#49 2017-2019 Toyota Highlander

CoPilot AI: It’s aC+” Buy

  • Fair Price - $26 Above Market
  • Includes $138 Premium Upgrades
  • Dealer Rating - 4.6 stars
More details
2019 Toyota Highlander XLE AWD photo
24
Price Drop
2019 Toyota Highlander XLE AWD Glencoe, IL
Black 3.5L V6 Engine
$22,998 91.8k miles
•••

#24 2017-2019 Toyota Highlander

CoPilot AI: It’s aB-” Buy

  • Good Price - $941 Below Market
  • Includes $152 Premium Upgrades
  • CARFAX: One Owner
More details
1-25 of 115 results

2018 Toyota Highlander

Mid-size Crossover
Seats
7
Fuel Economy
21City MPG
27Hwy 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.