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
2019 Toyota Highlander Hybrid XLE AWD photo
1
Price Drop
2019 Toyota Highlander Hybrid XLE AWD Northbrook, IL
$28,990 77.8k miles
•••

#1 2018-2020 Toyota Highlander

CoPilot AI: It’s anA” Buy

  • $500 Price Drop
  • Great Price - $4,146 Below Market
  • CARFAX: Clean Title, Not a rental or commercial vehicle
See more about this car
2020 Toyota Highlander XLE AWD photo
2
Price Drop
2020 Toyota Highlander XLE AWD Chicago, IL
$30,715 47k miles
•••

#2 2018-2020 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • Good Price - $1,847 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 XLE AWD photo
3
Price Drop
2020 Toyota Highlander XLE AWD Chicago, IL
$32,366 38.9k miles
•••

#3 2018-2020 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • $402 Price Drop
  • Good Price - $1,674 Below Market
  • CARFAX: Clean Title, Not a rental or commercial vehicle
See more about this car
2020 Toyota Highlander XLE AWD photo
4
2020 Toyota Highlander XLE AWD Milwaukee, WI
$34,349 28.2k miles
•••

#4 2018-2020 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • Good Price - $1,094 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 Limited AWD photo
5
Price Drop
2020 Toyota Highlander Limited AWD Elmhurst, IL
$36,488 46k miles Certified
•••

#5 2018-2020 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • Fair Price - $871 Above Market
  • Includes $778 Premium Upgrades
  • CARFAX: One Owner, Clean Title
See more about this car
2019 Toyota Highlander Limited Platinum AWD photo
6
2019 Toyota Highlander Limited Platinum AWD Rockford, IL
$34,995 16.9k miles
•••

#6 2018-2020 Toyota Highlander

CoPilot AI: It’s aB+” Buy

  • Great Price - $2,644 Below Market
  • CARFAX: Clean Title, Not a rental or commercial vehicle
  • Very Low Mileage
See more about this car
2020 Toyota Highlander Platinum AWD photo
7
2020 Toyota Highlander Platinum AWD St. Charles, IL
$36,995 35.8k miles
•••

#7 2018-2020 Toyota Highlander

CoPilot AI: It’s aB+” Buy

  • Great Price - $2,631 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
  • Very Low Mileage
See more about this car
2019 Toyota Highlander Limited AWD photo
8
Price Drop
2019 Toyota Highlander Limited AWD Countryside, IL
$32,888 39.6k miles
•••

#8 2018-2020 Toyota Highlander

CoPilot AI: It’s aB+” Buy

  • $111 Price Drop
  • Great Price - $2,501 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
2019 Toyota Highlander SE AWD photo
9
Price Drop
2019 Toyota Highlander SE AWD Lisle, IL
$24,937 88.9k miles
•••

#9 2018-2020 Toyota Highlander

CoPilot AI: It’s aB+” Buy

  • $60 Price Drop
  • Great Price - $2,118 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
2019 Toyota Highlander XLE AWD photo
10
Price Drop
2019 Toyota Highlander XLE AWD Lisle, IL
$27,380 67.7k miles
•••

#10 2018-2020 Toyota Highlander

CoPilot AI: It’s aB+” Buy

  • $20 Price Drop
  • Good Price - $1,662 Below Market
  • CARFAX: Clean Title, Not a rental or commercial vehicle
See more about this car
2019 Toyota Highlander LE AWD photo
11
Price Drop
2019 Toyota Highlander LE AWD Hodgkins, IL
$19,782 144.5k miles
•••

#11 2018-2020 Toyota Highlander

CoPilot AI: It’s aB+” Buy

  • $216 Price Drop
  • Great Price - $1,285 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
2019 Toyota Highlander XLE AWD photo
12
Price Drop
2019 Toyota Highlander XLE AWD Streamwood, IL
$24,490 103.7k miles Certified
•••

#12 2018-2020 Toyota Highlander

CoPilot AI: It’s aB+” Buy

  • $300 Price Drop
  • Good Price - $1,281 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
2019 Toyota Highlander XLE AWD photo
13
2019 Toyota Highlander XLE AWD Michigan City, IN
$25,500 92k miles
•••

#13 2018-2020 Toyota Highlander

CoPilot AI: It’s aB+” Buy

  • Good Price - $978 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
  • Dealer Rating - 4.3 stars
See more about this car
2019 Toyota Highlander Limited Platinum AWD photo
14
Price Drop
2019 Toyota Highlander Limited Platinum AWD Clarendon Hills, IL
$35,814 27.2k miles
•••

#14 2018-2020 Toyota Highlander

CoPilot AI: It’s aB+” Buy

  • $81 Price Drop
  • Fair Price - $823 Below Market
  • Includes $518 Premium Upgrades
See more about this car
2020 Toyota Highlander XLE AWD photo
15
2020 Toyota Highlander XLE AWD Lake Villa, IL
$34,209 31.4k miles
•••

#15 2018-2020 Toyota Highlander

CoPilot AI: It’s aB+” Buy

  • Fair Price - $327 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
  • Very Low Mileage
See more about this car
2020 Toyota Highlander LE AWD photo
16
Price Drop
2020 Toyota Highlander LE AWD Fox Lake, IL
$30,253 19.5k miles
•••

#16 2018-2020 Toyota Highlander

CoPilot AI: It’s aB+” Buy

  • $419 Price Drop
  • Fair Price - $250 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
2020 Toyota Highlander L AWD photo
17
2020 Toyota Highlander L AWD Streamwood, IL
$31,490 5.8k miles
•••

#17 2018-2020 Toyota Highlander

CoPilot AI: It’s aB+” Buy

  • Fair Price - $197 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
  • Very Low Mileage
See more about this car
2018 Toyota Highlander Limited AWD photo
18
Price Drop
2018 Toyota Highlander Limited AWD Schererville, IN
$29,000 61.4k miles Certified
•••

#18 2018-2020 Toyota Highlander

CoPilot AI: It’s aB+” Buy

  • $200 Price Drop
  • Fair Price - $105 Below Market
  • Includes $161 Premium Upgrades
See more about this car
2020 Toyota Highlander XLE AWD photo
19
Price Drop
2020 Toyota Highlander XLE AWD Streamwood, IL
$34,090 33.4k miles
•••

#19 2018-2020 Toyota Highlander

CoPilot AI: It’s aB+” Buy

  • $300 Price Drop
  • Fair Price - $102 Below Market
  • CARFAX: One Owner, Clean Title
See more about this car
2020 Toyota Highlander LE AWD photo
20
Price Drop
2020 Toyota Highlander LE AWD Palatine, IL
$29,283 33.9k miles
•••

#20 2018-2020 Toyota Highlander

CoPilot AI: It’s aB+” Buy

  • $608 Price Drop
  • Fair Price - $63 Above Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
2020 Toyota Highlander L AWD photo
21
Price Drop
2020 Toyota Highlander L AWD Westmont, IL
$29,600 32.8k miles
•••

#21 2018-2020 Toyota Highlander

CoPilot AI: It’s aB+” Buy

  • $300 Price Drop
  • Fair Price - $146 Above Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
2020 Toyota Highlander LE FWD photo
22
2020 Toyota Highlander LE FWD Milwaukee, WI
$28,527 35.8k miles
•••

#22 2018-2020 Toyota Highlander

CoPilot AI: It’s aB+” Buy

  • Fair Price - $208 Above Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
  • Very Low Mileage
See more about this car
2018 Toyota Highlander Limited AWD photo
23
Price Drop
2018 Toyota Highlander Limited AWD Schererville, IN
$28,800 65.6k miles Certified
•••

#23 2018-2020 Toyota Highlander

CoPilot AI: It’s aB+” Buy

  • $400 Price Drop
  • Fair Price - $227 Above Market
  • Includes $159 Premium Upgrades
See more about this car
2020 Toyota Highlander L AWD photo
24
Price Drop
2020 Toyota Highlander L AWD Milwaukee, WI
$29,300 30.5k miles
•••

#24 2018-2020 Toyota Highlander

CoPilot AI: It’s aB+” Buy

  • $689 Price Drop
  • Fair Price - $446 Above Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
2019 Toyota Highlander Limited Platinum AWD photo
25
Price Drop
2019 Toyota Highlander Limited Platinum AWD Calumet City, IL
$34,973 42.2k miles Certified
•••

#25 2018-2020 Toyota Highlander

CoPilot AI: It’s aB+” Buy

  • $200 Price Drop
  • Fair Price - $508 Above Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
1-25 of 133 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.