AI-Assisted Car Shopping

 New Search
Save
Sort

Used 2020 Toyota Highlander for Sale in Chicago, IL

Highlanders for Sale at Dealers, Ranked by CoPilot AI ?

Filters
Price
Year
Mileage
Trim
2020 Toyota Highlander Limited AWD photo
1
Price Drop
2020 Toyota Highlander Limited AWD Schererville, IN
$37,300 27k miles
•••

#1 2019-2021 Toyota Highlander

CoPilot AI: It’s anA+” Buy

  • $700 Price Drop
  • Great Price - $2,402 Below Market
  • Includes $1,319 Premium Upgrades
See more about this car
2021 Toyota Highlander XSE FWD photo
2
2021 Toyota Highlander XSE FWD Elmhurst, IL
$34,449 24.7k miles
•••

#2 2019-2021 Toyota Highlander

CoPilot AI: It’s anA+” Buy

  • Great Price - $4,207 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
  • Very Low Mileage
See more about this car
2021 Toyota Highlander XLE AWD photo
3
Price Drop
2021 Toyota Highlander XLE AWD Bartlett, IL
$33,790 29.7k miles
•••

#3 2019-2021 Toyota Highlander

CoPilot AI: It’s anA+” Buy

  • $200 Price Drop
  • Great Price - $2,561 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
2019 Toyota Highlander XLE AWD photo
4
Price Drop
2019 Toyota Highlander XLE AWD Schererville, IN
$29,200 44.4k miles
•••

#4 2019-2021 Toyota Highlander

CoPilot AI: It’s anA+” Buy

  • $700 Price Drop
  • Great Price - $2,188 Below Market
  • CARFAX: One Owner, Clean Title
See more about this car
2021 Toyota Highlander XLE AWD photo
5
2021 Toyota Highlander XLE AWD Sturtevant, WI
$31,455 57.1k miles
•••

#5 2019-2021 Toyota Highlander

CoPilot AI: It’s anA+” Buy

  • Great Price - $2,031 Below Market
  • Includes $789 Premium Upgrades
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
2019 Toyota Highlander XLE AWD photo
6
Price Drop
2019 Toyota Highlander XLE AWD Morton Grove, IL
$27,247 59.6k miles
•••

#6 2019-2021 Toyota Highlander

CoPilot AI: It’s anA+” Buy

  • $53 Price Drop
  • Great Price - $1,808 Below Market
  • CARFAX: Clean Title, Not a rental or commercial vehicle
See more about this car
2019 Toyota Highlander Hybrid XLE AWD photo
7
2019 Toyota Highlander Hybrid XLE AWD Northbrook, IL
$30,490 77.8k miles
•••

#7 2019-2021 Toyota Highlander

CoPilot AI: It’s anA” Buy

  • Great Price - $3,573 Below Market
  • CARFAX: Clean Title, Not a rental or commercial vehicle
  • Average Mileage
See more about this car
2021 Toyota Highlander XSE AWD photo
8
2021 Toyota Highlander XSE AWD Milwaukee, WI
$38,659 27.4k miles
•••

#8 2019-2021 Toyota Highlander

CoPilot AI: It’s anA” Buy

  • Good Price - $1,266 Below Market
  • Includes $1,903 Premium Upgrades
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
2021 Toyota Highlander XLE AWD photo
9
Price Drop
2021 Toyota Highlander XLE AWD Northbrook, IL
$34,990 30.1k miles
•••

#9 2019-2021 Toyota Highlander

CoPilot AI: It’s anA” Buy

  • $500 Price Drop
  • Good Price - $1,095 Below Market
  • Includes $832 Premium Upgrades
See more about this car
2020 Toyota Highlander Hybrid Platinum AWD photo
10
Price Drop
2020 Toyota Highlander Hybrid Platinum AWD Schererville, IN
$41,500 29.8k miles
•••

#10 2019-2021 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • $200 Price Drop
  • Good Price - $2,344 Below Market
  • Includes $429 Premium Upgrades
See more about this car
2021 Toyota Highlander Hybrid XLE AWD photo
11
2021 Toyota Highlander Hybrid XLE AWD Palatine, IL
$36,695 39.1k miles
•••

#11 2019-2021 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • Good Price - $1,974 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
  • Motivation to Negotiate - Increasing
See more about this car
2020 Toyota Highlander XLE AWD photo
12
Price Drop
2020 Toyota Highlander XLE AWD Chicago, IL
$30,715 47k miles
•••

#12 2019-2021 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • Good Price - $1,851 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
  • Motivation to Negotiate - Very High
See more about this car
2021 Toyota Highlander XLE AWD photo
13
Price Drop
2021 Toyota Highlander XLE AWD Bartlett, IL
$33,890 34.5k miles
•••

#13 2019-2021 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • $100 Price Drop
  • Good Price - $1,507 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
2020 Toyota Highlander Limited AWD photo
14
Price Drop
2020 Toyota Highlander Limited AWD Naperville, IL
$33,379 60.4k miles
•••

#14 2019-2021 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • $11,120 Price Drop
  • Good Price - $1,494 Below Market
  • Includes $760 Premium Upgrades
See more about this car
2020 Toyota Highlander XLE AWD photo
15
2020 Toyota Highlander XLE AWD Chicago, IL
$32,768 38.9k miles
•••

#15 2019-2021 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • Good Price - $1,286 Below Market
  • CARFAX: Clean Title, Not a rental or commercial vehicle
  • Motivation to Negotiate - Increasing
See more about this car
2021 Toyota Highlander Hybrid XLE AWD photo
16
2021 Toyota Highlander Hybrid XLE AWD St. Charles, IL
$37,919 38.6k miles
•••

#16 2019-2021 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • Good Price - $1,279 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
  • Below Average Mileage
See more about this car
2021 Toyota Highlander Limited AWD photo
17
Price Drop
2021 Toyota Highlander Limited AWD Elkhart, IN
$37,890 40.1k miles
•••

#17 2019-2021 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • $400 Price Drop
  • Good Price - $1,215 Below Market
  • Includes $831 Premium Upgrades
See more about this car
2021 Toyota Highlander XLE AWD photo
18
Price Drop
2021 Toyota Highlander XLE AWD Bartlett, IL
$35,290 27.8k miles
•••

#18 2019-2021 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • $100 Price Drop
  • Good Price - $1,153 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
2021 Toyota Highlander XSE AWD photo
19
2021 Toyota Highlander XSE AWD Brookfield, WI
$37,101 38.3k miles
•••

#19 2019-2021 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • Fair Price - $1,117 Below Market
  • Includes $1,344 Premium Upgrades
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
2021 Toyota Highlander XLE AWD photo
20
Price Drop
2021 Toyota Highlander XLE AWD North Aurora, IL
$34,629 25.2k miles
•••

#20 2019-2021 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • $321 Price Drop
  • Good Price - $1,102 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
2021 Toyota Highlander XLE AWD photo
21
Price Drop
2021 Toyota Highlander XLE AWD Naperville, IL
$35,414 33.7k miles
•••

#21 2019-2021 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • $576 Price Drop
  • Fair Price - $1,023 Below Market
  • Includes $1,391 Premium Upgrades
See more about this car
2021 Toyota Highlander XLE AWD photo
22
Price Drop
2021 Toyota Highlander XLE AWD Naperville, IL
$35,577 31.5k miles
•••

#22 2019-2021 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • $400 Price Drop
  • Fair Price - $993 Below Market
  • Includes $832 Premium Upgrades
See more about this car
2021 Toyota Highlander Limited AWD photo
23
Price Drop
2021 Toyota Highlander Limited AWD North Aurora, IL
$37,551 39.4k miles
•••

#23 2019-2021 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • $278 Price Drop
  • Fair Price - $934 Below Market
  • Includes $832 Premium Upgrades
See more about this car
2021 Toyota Highlander Limited AWD photo
24
2021 Toyota Highlander Limited AWD Lombard, IL
$37,995 33.2k miles
•••

#24 2019-2021 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • Fair Price - $898 Below Market
  • Includes $840 Premium Upgrades
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
2021 Toyota Highlander XSE AWD photo
25
Price Drop
2021 Toyota Highlander XSE AWD Milwaukee, WI
$38,995 21.7k miles
•••

#25 2019-2021 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • $248 Price Drop
  • Fair Price - $847 Below Market
  • Includes $1,344 Premium Upgrades
See more about this car
1-25 of 234 results

2020 Toyota Highlander

Mid-size Crossover
Seats
7
Fuel Economy
36 - 36City MPG
35 - 35Hwy 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.