AI-Assisted Car Shopping

 New Search
Save
Sort

Used 2019 Toyota Highlander for Sale in Chicago, IL

Highlanders for Sale at Dealers, Ranked by CoPilot AI ?

Filters
Price
Year
Mileage
Trim
2018 Toyota Highlander Limited Platinum AWD photo
1
Toyota Highlander Limited Platinum AWD Libertyville, IL
$27,995 54.6k miles
•••

#1 2018-2020 Toyota Highlander

CoPilot AI: It’s anA+” Buy

  • Great Price - $1,800 Below Market
  • Includes $154 Premium Upgrades
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
2019 Toyota Highlander Hybrid XLE AWD photo
2
Price Drop
Toyota Highlander Hybrid XLE AWD Northbrook, IL
$28,490 77.8k miles
•••

#2 2018-2020 Toyota Highlander

CoPilot AI: It’s anA” Buy

  • $498 Price Drop
  • Great Price - $4,158 Below Market
  • CARFAX: Clean Title, Not a rental or commercial vehicle
See more about this car
2019 Toyota Highlander XLE AWD photo
3
Price Drop
Toyota Highlander XLE AWD Michigan City, IN
$24,955 92.1k miles
•••

#3 2018-2020 Toyota Highlander

CoPilot AI: It’s anA” Buy

  • $1 Price Drop
  • Great Price - $1,978 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
2019 Toyota Highlander XLE FWD photo
4
Toyota Highlander XLE FWD Glencoe, IL
$24,991 82.3k miles
•••

#4 2018-2020 Toyota Highlander

CoPilot AI: It’s anA” Buy

  • Great Price - $1,929 Below Market
  • Includes $501 Premium Upgrades
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
2020 Toyota Highlander Hybrid Limited AWD photo
5
Toyota Highlander Hybrid Limited AWD Palatine, IL
$37,550 26.6k miles
•••

#5 2018-2020 Toyota Highlander

CoPilot AI: It’s anA” Buy

  • Good Price - $1,471 Below Market
  • Includes $813 Premium Upgrades
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
2020 Toyota Highlander XLE AWD photo
6
Price Drop
Toyota Highlander XLE AWD Chicago, IL
$30,715 47.1k miles
•••

#6 2018-2020 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • Good Price - $1,653 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
  • Motivation to Negotiate - Very High
See more about this car
2020 Toyota Highlander LE AWD photo
7
Price Drop
Toyota Highlander LE AWD Fox Lake, IL
$30,000 19.5k miles
•••

#7 2018-2020 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • $253 Price Drop
  • Good Price - $1,480 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
2019 Toyota Highlander Hybrid XLE AWD photo
8
Price Drop
Toyota Highlander Hybrid XLE AWD Merrillville, IN
$31,750 56.1k miles Certified
•••

#8 2018-2020 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • $238 Price Drop
  • Good Price - $1,302 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
2019 Toyota Highlander XLE AWD photo
9
Toyota Highlander XLE AWD Aurora, IL
$29,000 59.1k miles
•••

#9 2018-2020 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • Good Price - $1,063 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
  • Below Average Mileage
See more about this car
2018 Toyota Highlander XLE AWD photo
10
Price Drop
Toyota Highlander XLE AWD Joliet, IL
$29,253 61.1k miles
•••

#10 2018-2020 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • $1,688 Price Drop
  • Fair Price - $406 Below Market
  • Includes $913 Premium Upgrades
See more about this car
2018 Toyota Highlander XLE AWD photo
11
Price Drop
Toyota Highlander XLE AWD Waukesha, WI
$21,888 102.7k miles
•••

#11 2018-2020 Toyota Highlander

CoPilot AI: It’s aB+” Buy

  • $2,671 Price Drop
  • Great Price - $3,178 Below Market
  • Includes $560 Premium Upgrades
See more about this car
2019 Toyota Highlander SE AWD photo
12
Price Drop
Toyota Highlander SE AWD Lisle, IL
$24,854 88.9k miles
•••

#12 2018-2020 Toyota Highlander

CoPilot AI: It’s aB+” Buy

  • $83 Price Drop
  • Great Price - $2,400 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
2019 Toyota Highlander LE AWD photo
13
Price Drop
Toyota Highlander LE AWD Hodgkins, IL
$18,994 144.5k miles
•••

#13 2018-2020 Toyota Highlander

CoPilot AI: It’s aB+” Buy

  • $788 Price Drop
  • Great Price - $1,384 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
2019 Toyota Highlander XLE AWD photo
14
Toyota Highlander XLE AWD Highland, IN
$26,988 78.9k miles
•••

#14 2018-2020 Toyota Highlander

CoPilot AI: It’s aB+” Buy

  • Good Price - $1,188 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
  • Dealer Rating - 4.5 stars
See more about this car
2018 Toyota Highlander Limited AWD photo
15
Toyota Highlander Limited AWD Schererville, IN
$26,200 84.7k miles Certified
•••

#15 2018-2020 Toyota Highlander

CoPilot AI: It’s aB+” Buy

  • Good Price - $989 Below Market
  • Includes $151 Premium Upgrades
  • CARFAX: Clean Title, Not a rental or commercial vehicle
See more about this car
2019 Toyota Highlander LE AWD photo
16
Price Drop
Toyota Highlander LE AWD Fox Lake, IL
$23,300 75.7k miles
•••

#16 2018-2020 Toyota Highlander

CoPilot AI: It’s aB+” Buy

  • $100 Price Drop
  • Good Price - $988 Below Market
  • CARFAX: Clean Title
See more about this car
2020 Toyota Highlander L AWD photo
17
Price Drop
Toyota Highlander L AWD Milwaukee, WI
$26,100 80k miles
•••

#17 2018-2020 Toyota Highlander

CoPilot AI: It’s aB+” Buy

  • $498 Price Drop
  • Good Price - $918 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
2019 Toyota Highlander XLE AWD photo
18
Toyota Highlander XLE AWD Streamwood, IL
$27,990 70.9k miles
•••

#18 2018-2020 Toyota Highlander

CoPilot AI: It’s aB+” Buy

  • Good Price - $915 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
  • Motivation to Negotiate - Increasing
See more about this car
2018 Toyota Highlander Limited AWD photo
19
Price Drop
Toyota Highlander Limited AWD Schererville, IN
$27,700 65.6k miles Certified
•••

#19 2018-2020 Toyota Highlander

CoPilot AI: It’s aB+” Buy

  • $300 Price Drop
  • Fair Price - $848 Below Market
  • Includes $159 Premium Upgrades
See more about this car
2018 Toyota Highlander Limited Platinum AWD photo
20
Price Drop
Toyota Highlander Limited Platinum AWD Northfield, IL
$27,989 68.7k miles
•••

#20 2018-2020 Toyota Highlander

CoPilot AI: It’s aB+” Buy

  • $1,000 Price Drop
  • Fair Price - $821 Below Market
  • Includes $148 Premium Upgrades
See more about this car
2020 Toyota Highlander XLE AWD photo
21
Toyota Highlander XLE AWD Milwaukee, WI
$34,349 28.2k miles
•••

#21 2018-2020 Toyota Highlander

CoPilot AI: It’s aB+” Buy

  • Fair Price - $706 Below Market
  • Includes $559 Premium Upgrades
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
2020 Toyota Highlander XLE AWD photo
22
Price Drop
Toyota Highlander XLE AWD Northbrook, IL
$34,990 15.8k miles
•••

#22 2018-2020 Toyota Highlander

CoPilot AI: It’s aB+” Buy

  • $500 Price Drop
  • Fair Price - $659 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
2018 Toyota Highlander XLE AWD photo
23
Toyota Highlander XLE AWD West Allis, WI
$27,990 62.4k miles
•••

#23 2018-2020 Toyota Highlander

CoPilot AI: It’s aB+” Buy

  • Fair Price - $71 Below Market
  • Includes $168 Premium Upgrades
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
2018 Toyota Highlander Limited AWD photo
24
Price Drop
Toyota Highlander Limited AWD Schererville, IN
$29,000 61.4k miles Certified
•••

#24 2018-2020 Toyota Highlander

CoPilot AI: It’s aB+” Buy

  • $200 Price Drop
  • Fair Price - $68 Below Market
  • Includes $161 Premium Upgrades
See more about this car
2020 Toyota Highlander XLE AWD photo
25
Toyota Highlander XLE AWD Lake Villa, IL
$34,209 31.4k miles
•••

#25 2018-2020 Toyota Highlander

CoPilot AI: It’s aB+” Buy

  • Fair Price - $13 Above Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
  • Motivation to Negotiate - Increasing
See more about this car
1-25 of 138 results

2019 Toyota Highlander

Mid-size Crossover
Seats
7
Fuel Economy
29 - 29City MPG
27 - 27Hwy MPG
NHTSA Rating Summary
Copilot Rating
Dimensions

Why Use CoPilot?

Shop and buy your next car with confidence. CoPilot searches every car at every dealer, every day, and ranks them based on what matters to you.


When you shop for a new or used car, CoPilot helps you know more. We search every car at every dealer so you don't have to, we give you data and insights you won't find anywhere else, and we rank every car so it's easy to find the best car at the best price.


When you're ready to buy your next car, CoPilot helps you make sure you never get taken advantage of at the dealership. Would you like to know more than the salesperson? CoPilot helps you avoid any tricks, traps, and scams. Know how and what you can negotiate. With CoPilot, you'll save time, money, and frustration.

© 2024 CoPilot. All Rights Reserved.