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
2021 Toyota Highlander XSE AWD photo
1
Price Drop
2021 Toyota Highlander XSE AWD Milwaukee, WI
$36,490 27.4k miles
•••

#1 2019-2021 Toyota Highlander

CoPilot AI: It’s anA+” Buy

  • $501 Price Drop
  • Great Price - $3,208 Below Market
  • Includes $1,903 Premium Upgrades
See more about this car
2021 Toyota Highlander XLE AWD photo
2
2021 Toyota Highlander XLE AWD Northbrook, IL
$34,000 30.1k miles
•••

#2 2019-2021 Toyota Highlander

CoPilot AI: It’s anA+” Buy

  • Great Price - $2,206 Below Market
  • Includes $832 Premium Upgrades
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
2021 Toyota Highlander XSE FWD photo
3
2021 Toyota Highlander XSE FWD Elmhurst, IL
$34,449 24.7k miles
•••

#3 2019-2021 Toyota Highlander

CoPilot AI: It’s anA+” Buy

  • Great Price - $4,440 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
  • Motivation to Negotiate - Increasing
See more about this car
2021 Toyota Highlander XSE AWD photo
4
Price Drop
2021 Toyota Highlander XSE AWD Milwaukee, WI
$34,259 51.5k miles
•••

#4 2019-2021 Toyota Highlander

CoPilot AI: It’s anA+” Buy

  • $961 Price Drop
  • Great Price - $2,232 Below Market
  • Includes $1,305 Premium Upgrades
See more about this car
2019 Toyota Highlander Hybrid XLE AWD photo
5
Price Drop
2019 Toyota Highlander Hybrid XLE AWD Northbrook, IL
$28,990 77.8k miles
•••

#5 2019-2021 Toyota Highlander

CoPilot AI: It’s anA” Buy

  • $500 Price Drop
  • Great Price - $4,129 Below Market
  • CARFAX: Clean Title, Not a rental or commercial vehicle
See more about this car
2021 Toyota Highlander Hybrid Platinum AWD photo
6
Price Drop
2021 Toyota Highlander Hybrid Platinum AWD Gurnee, IL
$38,225 57.2k miles
•••

#6 2019-2021 Toyota Highlander

CoPilot AI: It’s anA” Buy

  • $701 Price Drop
  • Great Price - $2,658 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
2021 Toyota Highlander XLE AWD photo
7
Price Drop
2021 Toyota Highlander XLE AWD South Bend, IN
$33,006 49k miles
•••

#7 2019-2021 Toyota Highlander

CoPilot AI: It’s anA” Buy

  • $425 Price Drop
  • Great Price - $2,626 Below Market
  • Includes $820 Premium Upgrades
See more about this car
2021 Toyota Highlander Limited FWD photo
8
Price Drop
2021 Toyota Highlander Limited FWD Milwaukee, WI
$37,057 19.8k miles
•••

#8 2019-2021 Toyota Highlander

CoPilot AI: It’s anA” Buy

  • $909 Price Drop
  • Good Price - $2,304 Below Market
  • Includes $1,054 Premium Upgrades
See more about this car
2021 Toyota Highlander XLE AWD photo
9
Price Drop
2021 Toyota Highlander XLE AWD Chicago, IL
$35,732 23.1k miles
•••

#9 2019-2021 Toyota Highlander

CoPilot AI: It’s anA” Buy

  • $42 Price Drop
  • Good Price - $2,074 Below Market
  • Includes $1,311 Premium Upgrades
See more about this car
2021 Toyota Highlander XSE AWD photo
10
Price Drop
2021 Toyota Highlander XSE AWD Milwaukee, WI
$37,590 23.8k miles
•••

#10 2019-2021 Toyota Highlander

CoPilot AI: It’s anA” Buy

  • $1,010 Price Drop
  • Good Price - $1,768 Below Market
  • Includes $1,344 Premium Upgrades
See more about this car
2021 Toyota Highlander XLE AWD photo
11
2021 Toyota Highlander XLE AWD Bartlett, IL
$35,490 28.2k miles
•••

#11 2019-2021 Toyota Highlander

CoPilot AI: It’s anA” Buy

  • Good Price - $1,750 Below Market
  • Includes $832 Premium Upgrades
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
2021 Toyota Highlander XSE AWD photo
12
Price Drop
2021 Toyota Highlander XSE AWD Brookfield, WI
$36,500 38.3k miles
•••

#12 2019-2021 Toyota Highlander

CoPilot AI: It’s anA” Buy

  • $500 Price Drop
  • Good Price - $1,729 Below Market
  • Includes $1,344 Premium Upgrades
See more about this car
2021 Toyota Highlander XLE AWD photo
13
Price Drop
2021 Toyota Highlander XLE AWD Brookfield, WI
$35,167 35k miles
•••

#13 2019-2021 Toyota Highlander

CoPilot AI: It’s anA” Buy

  • $280 Price Drop
  • Good Price - $1,233 Below Market
  • Includes $832 Premium Upgrades
See more about this car
2021 Toyota Highlander XLE AWD photo
14
Price Drop
2021 Toyota Highlander XLE AWD South Bend, IN
$35,420 27.7k miles
•••

#14 2019-2021 Toyota Highlander

CoPilot AI: It’s anA” Buy

  • $797 Price Drop
  • Good Price - $1,125 Below Market
  • Includes $832 Premium Upgrades
See more about this car
2021 Toyota Highlander XLE AWD photo
15
2021 Toyota Highlander XLE AWD Romeoville, IL
$35,000 28.4k miles
•••

#15 2019-2021 Toyota Highlander

CoPilot AI: It’s anA” Buy

  • Good Price - $1,123 Below Market
  • Includes $832 Premium Upgrades
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
2021 Toyota Highlander Hybrid XLE AWD photo
16
Price Drop
2021 Toyota Highlander Hybrid XLE AWD Schaumburg, IL
$36,488 39.1k miles
•••

#16 2019-2021 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • $207 Price Drop
  • Good Price - $2,300 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
2021 Toyota Highlander XLE AWD photo
17
Price Drop
2021 Toyota Highlander XLE AWD Mishawaka, IN
$33,597 29.7k miles
•••

#17 2019-2021 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • $401 Price Drop
  • Good Price - $2,133 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
2020 Toyota Highlander XLE AWD photo
18
Price Drop
2020 Toyota Highlander XLE AWD Chicago, IL
$30,715 47k miles
•••

#18 2019-2021 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • Good Price - $1,824 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
19
Price Drop
2021 Toyota Highlander XLE AWD Greenfield, WI
$33,900 45.6k miles
•••

#19 2019-2021 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • $99 Price Drop
  • Good Price - $1,726 Below Market
  • Includes $1,380 Premium Upgrades
See more about this car
2021 Toyota Highlander LE AWD photo
20
Price Drop
2021 Toyota Highlander LE AWD Oak Lawn, IL
$29,900 35.7k miles
•••

#20 2019-2021 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • $100 Price Drop
  • Good Price - $1,720 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 Northbrook, IL
$33,990 37.7k miles
•••

#21 2019-2021 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • $500 Price Drop
  • Good Price - $1,686 Below Market
  • 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
2020 Toyota Highlander XLE AWD Chicago, IL
$32,366 38.9k miles
•••

#22 2019-2021 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • $402 Price Drop
  • Good Price - $1,636 Below Market
  • CARFAX: Clean Title, Not a rental or commercial vehicle
See more about this car
2021 Toyota Highlander XLE AWD photo
23
Price Drop
2021 Toyota Highlander XLE AWD North Aurora, IL
$35,999 17.5k miles
•••

#23 2019-2021 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • $1,000 Price Drop
  • Good Price - $1,627 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
2021 Toyota Highlander XLE AWD photo
24
2021 Toyota Highlander XLE AWD Streamwood, IL
$33,990 34.5k miles
•••

#24 2019-2021 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • Good Price - $1,592 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
  • Motivation to Negotiate - Increasing
See more about this car
2021 Toyota Highlander XLE AWD photo
25
Price Drop
2021 Toyota Highlander XLE AWD Northbrook, IL
$34,490 27.1k miles
•••

#25 2019-2021 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • $500 Price Drop
  • Good Price - $1,574 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
1-25 of 311 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.