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
2020 Toyota Highlander LE AWD photo
1
Price Drop
2020 Toyota Highlander LE AWD • Joliet, IL
Black • 3.5L V6 Engine
$21,800 • 97.9k miles
•••

#1 2016-2020 Toyota Highlander

CoPilot AI: It’s an “A” Buy

  • $149 Price Drop
  • Great Price - $3,597 Below Market
  • CARFAX: Clean Title
More details
2020 Toyota Highlander XLE AWD photo
2
2020 Toyota Highlander XLE AWD • Sturtevant, WI
Silver • 3.5L V6 Engine
$27,500 • 67.8k miles
•••

#2 2016-2020 Toyota Highlander

CoPilot AI: It’s an “A” Buy

  • Great Price - $1,912 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
  • Average Mileage
More details
2016 Toyota Highlander XLE AWD photo
3
Price Drop
2016 Toyota Highlander XLE AWD • Milwaukee, WI
Green • 3.5L V6 Engine
$17,995 • 118.7k miles
•••

#3 2016-2020 Toyota Highlander

CoPilot AI: It’s an “A” Buy

  • $1,000 Price Drop
  • Great Price - $1,294 Below Market
  • CARFAX: Clean Title, Not a rental or commercial vehicle
More details
2018 Toyota Highlander XLE AWD photo
4
2018 Toyota Highlander XLE AWD • Burlington, WI
White • 3.5L V6 Engine
$23,990 • 88.6k miles
•••

#4 2016-2020 Toyota Highlander

CoPilot AI: It’s an “A-” Buy

  • Good Price - $961 Below Market
  • Includes $886 Premium Upgrades
  • CARFAX: Clean Title, Not a rental or commercial vehicle
More details
2016 Toyota Highlander Limited FWD photo
5
Price Drop
2016 Toyota Highlander Limited FWD • Michigan City, IN
Black • 3.5L V6 Engine
$19,977 • 65k miles
•••

#5 2016-2020 Toyota Highlander

CoPilot AI: It’s a “B+” Buy

  • $1,000 Price Drop
  • Great Price - $3,231 Below Market
  • CARFAX: Clean Title, Not a rental or commercial vehicle
More details
2017 Toyota Highlander XLE AWD photo
6
2017 Toyota Highlander XLE AWD • Chicago, IL
Gray • 3.5L V6 Engine
$19,995 • 92.6k miles
•••

#6 2016-2020 Toyota Highlander

CoPilot AI: It’s a “B+” Buy

  • Great Price - $2,437 Below Market
  • CARFAX: Clean Title, Not a rental or commercial vehicle
  • Below Average Mileage
More details
2016 Toyota Highlander LE FWD photo
7
Price Drop
2016 Toyota Highlander LE FWD • Waukesha, WI
White • 2.7L I4 Engine
$10,724 • 196.9k miles
•••

#7 2016-2020 Toyota Highlander

CoPilot AI: It’s a “B+” Buy

  • $274 Price Drop
  • Great Price - $2,230 Below Market
  • CARFAX: Clean Title, Not a rental or commercial vehicle
More details
2016 Toyota Highlander XLE AWD photo
8
Price Drop
2016 Toyota Highlander XLE AWD • Libertyville, IL
Green • 3.5L V6 Engine
$11,988 • 201.3k miles
•••

#8 2016-2020 Toyota Highlander

CoPilot AI: It’s a “B+” Buy

  • $494 Price Drop
  • Great Price - $1,747 Below Market
  • CARFAX: Clean Title, Not a rental or commercial vehicle
More details
2017 Toyota Highlander XLE AWD photo
9
2017 Toyota Highlander XLE AWD • St. Charles, IL
Silver • 3.5L V6 Engine
$19,995 • 102k miles
•••

#9 2016-2020 Toyota Highlander

CoPilot AI: It’s a “B+” Buy

  • Great Price - $1,743 Below Market
  • CARFAX: Clean Title, Not a rental or commercial vehicle
  • Motivation to Negotiate - High
More details
2019 Toyota Highlander XLE AWD photo
10
Price Drop
2019 Toyota Highlander XLE AWD • Chicago, IL
Black • 3.5L V6 Engine
$25,299 • 70.2k miles
•••

#10 2016-2020 Toyota Highlander

CoPilot AI: It’s a “B+” Buy

  • $556 Price Drop
  • Great Price - $1,651 Below Market
  • CARFAX: Clean Title, Not a rental or commercial vehicle
More details
2018 Toyota Highlander XLE AWD photo
11
Price Drop
2018 Toyota Highlander XLE AWD • Janesville, WI
Silver • 3.5L V6 Engine
$22,000 • 99k miles
•••

#11 2016-2020 Toyota Highlander

CoPilot AI: It’s a “B+” Buy

  • $667 Price Drop
  • Great Price - $1,648 Below Market
  • Includes $524 Premium Upgrades
More details
2018 Toyota Highlander XLE AWD photo
12
Price Drop
2018 Toyota Highlander XLE AWD • Palatine, IL
Gray • 3.5L V6 Engine
$15,500 • 181k miles
•••

#12 2016-2020 Toyota Highlander

CoPilot AI: It’s a “B+” Buy

  • $2,490 Price Drop
  • Great Price - $1,607 Below Market
  • Includes $811 Premium Upgrades
More details
2019 Toyota Highlander XLE AWD photo
13
Price Drop
2019 Toyota Highlander XLE AWD • Merrillville, IN
Silver • 3.5L V6 Engine
$25,988 • 75.3k miles
•••

#13 2016-2020 Toyota Highlander

CoPilot AI: It’s a “B+” Buy

  • Good Price - $1,102 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
  • Motivation to Negotiate - High
More details
2016 Toyota Highlander Limited AWD photo
14
Price Drop
2016 Toyota Highlander Limited AWD • Libertyville, IL
Black • 3.5L V6 Engine
$18,250 • 128.7k miles
•••

#14 2016-2020 Toyota Highlander

CoPilot AI: It’s a “B+” Buy

  • $250 Price Drop
  • Good Price - $1,067 Below Market
  • CARFAX: Clean Title, Not a rental or commercial vehicle
More details
2019 Toyota Highlander SE AWD photo
15
Price Drop
2019 Toyota Highlander SE AWD • West Allis, WI
White • 3.5L V6 Engine
$29,390 • 44.8k miles
•••

#15 2016-2020 Toyota Highlander

CoPilot AI: It’s a “B+” Buy

  • $605 Price Drop
  • Fair Price - $895 Below Market
  • CARFAX: Clean Title, Not a rental or commercial vehicle
More details
2017 Toyota Highlander XLE AWD photo
16
2017 Toyota Highlander XLE AWD • Glendale Heights, IL
White • 3.5L V6 Engine
$20,995 • 104.1k miles
•••

#16 2016-2020 Toyota Highlander

CoPilot AI: It’s a “B+” Buy

  • Good Price - $845 Below Market
  • Includes $134 Premium Upgrades
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
More details
2018 Toyota Highlander XLE AWD photo
17
Price Drop
2018 Toyota Highlander XLE AWD • Glendale Heights, IL
Gray • 3.5L V6 Engine
$22,995 • 88.6k miles
•••

#17 2016-2020 Toyota Highlander

CoPilot AI: It’s a “B+” Buy

  • $1,000 Price Drop
  • Good Price - $825 Below Market
  • Includes $142 Premium Upgrades
More details
2019 Toyota Highlander XLE AWD photo
18
Price Drop
2019 Toyota Highlander XLE AWD • Chicago, IL
Green • 3.5L V6 Engine
$28,688 • 50k miles
•••

#18 2016-2020 Toyota Highlander

CoPilot AI: It’s a “B+” Buy

  • $312 Price Drop
  • Fair Price - $768 Below Market
  • Includes $379 Premium Upgrades
More details
2018 Toyota Highlander Limited Platinum AWD photo
19
Price Drop
2018 Toyota Highlander Limited Platinum AWD • Chicago, IL
Blue • 3.5L V6 Engine
$27,999 • 63.2k miles
•••

#19 2016-2020 Toyota Highlander

CoPilot AI: It’s a “B+” Buy

  • $127 Price Drop
  • Fair Price - $669 Below Market
  • Includes $148 Premium Upgrades
More details
2017 Toyota Highlander Limited AWD photo
20
2017 Toyota Highlander Limited AWD • St. Charles, IL
White • 3.5L V6 Engine
$18,500 • 144k miles
•••

#20 2016-2020 Toyota Highlander

CoPilot AI: It’s a “B+” Buy

  • Good Price - $593 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
  • Dealer Rating - 4.4 stars
More details
2019 Toyota Highlander LE Plus AWD photo
21
2019 Toyota Highlander LE Plus AWD • Elmhurst, IL
White • 3.5L V6 Engine
$25,999 • 63k miles
•••

#21 2016-2020 Toyota Highlander

CoPilot AI: It’s a “B+” Buy

  • Fair Price - $579 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
  • Below Average Mileage
More details
2020 Toyota Highlander Platinum AWD photo
22
Price Drop
2020 Toyota Highlander Platinum AWD • Milwaukee, WI
Red • 3.5L V6 Engine
$39,695 • 11.2k miles
•••

#22 2016-2020 Toyota Highlander

CoPilot AI: It’s a “B+” Buy

  • $149 Price Drop
  • Fair Price - $576 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
More details
2016 Toyota Highlander Limited AWD photo
23
Price Drop
2016 Toyota Highlander Limited AWD • Schaumburg, IL
3.5L V6 Engine
$22,998 • 71.9k miles
•••

#23 2016-2020 Toyota Highlander

CoPilot AI: It’s a “B+” Buy

  • $1,000 Price Drop
  • Fair Price - $363 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
More details
2019 Toyota Highlander Limited Platinum AWD photo
24
2019 Toyota Highlander Limited Platinum AWD • St. Charles, IL
Black • 3.5L V6 Engine
$30,500 • 63.1k miles • Certified
•••

#24 2016-2020 Toyota Highlander

CoPilot AI: It’s a “B+” Buy

  • Fair Price - $279 Below Market
  • Includes $435 Premium Upgrades
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
More details
2020 Toyota Highlander Hybrid Platinum AWD photo
25
Price Drop
2020 Toyota Highlander Hybrid Platinum AWD • Naperville, IL
Gray • 2.5L I4 Engine
$40,598 • 46.7k miles • Certified
•••

#25 2016-2020 Toyota Highlander

CoPilot AI: It’s a “B+” Buy

  • $400 Price Drop
  • Fair Price - $214 Above Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
More details
1-25 of 142 results
HomeToyotaHighlander

2018 Toyota Highlander

Mid-size Crossover
Seats
7
Fuel Economy
29City MPG
27Hwy MPG
NHTSA Rating Summary
Copilot Rating
Dimensions
Most Popular Models like Highlander
Other Years
Research More Models
View more SUVs

© 2025 CoPilot. All Rights Reserved.