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Used 2021 Toyota Highlander for Sale in Chicago, IL

Highlanders for Sale at Dealers, Ranked by CoPilot AI ?

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2021 Toyota Highlander XSE AWD photo
1
Price Drop
Toyota Highlander XSE AWD Lincolnwood, IL
$36,388 18.5k miles
•••

#1 2021 Toyota Highlander

CoPilot AI: It’s anA+” Buy

  • $200 Price Drop
  • Great Price - $3,063 Below Market
  • Includes $1,344 Premium Upgrades
See more about this car
2021 Toyota Highlander XSE FWD photo
2
Price Drop
Toyota Highlander XSE FWD Elmhurst, IL
$33,051 24.7k miles
•••

#2 2021 Toyota Highlander

CoPilot AI: It’s anA+” Buy

  • $355 Price Drop
  • Great Price - $5,242 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
2021 Toyota Highlander XLE AWD photo
3
Price Drop
Toyota Highlander XLE AWD Northbrook, IL
$32,990 37.7k miles
•••

#3 2021 Toyota Highlander

CoPilot AI: It’s anA+” Buy

  • $500 Price Drop
  • Great Price - $2,647 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
2021 Toyota Highlander LE AWD photo
4
Price Drop
Toyota Highlander LE AWD Oak Lawn, IL
$29,500 35.7k miles
•••

#4 2021 Toyota Highlander

CoPilot AI: It’s anA+” Buy

  • $400 Price Drop
  • Great Price - $2,063 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
2021 Toyota Highlander Hybrid Platinum AWD photo
5
Price Drop
Toyota Highlander Hybrid Platinum AWD Palatine, IL
$36,526 58k miles
•••

#5 2021 Toyota Highlander

CoPilot AI: It’s anA” Buy

  • Great Price - $5,084 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
6
Toyota Highlander XLE AWD South Bend, IN
$33,332 49k miles
•••

#6 2021 Toyota Highlander

CoPilot AI: It’s anA” Buy

  • Great Price - $2,183 Below Market
  • Includes $817 Premium Upgrades
  • CARFAX: Clean Title
See more about this car
2021 Toyota Highlander XLE AWD photo
7
Price Drop
Toyota Highlander XLE AWD Mt Pleasant, WI
$34,597 32.8k miles
•••

#7 2021 Toyota Highlander

CoPilot AI: It’s anA” Buy

  • $393 Price Drop
  • Good Price - $1,885 Below Market
  • Includes $832 Premium Upgrades
See more about this car
2021 Toyota Highlander XLE AWD photo
8
Price Drop
Toyota Highlander XLE AWD West Allis, WI
$35,490 30.3k miles
•••

#8 2021 Toyota Highlander

CoPilot AI: It’s anA” Buy

  • $500 Price Drop
  • Good Price - $1,399 Below Market
  • Includes $832 Premium Upgrades
See more about this car
2021 Toyota Highlander XLE AWD photo
9
Price Drop
Toyota Highlander XLE AWD West Allis, WI
$34,490 38.1k miles
•••

#9 2021 Toyota Highlander

CoPilot AI: It’s anA” Buy

  • $501 Price Drop
  • Good Price - $1,377 Below Market
  • Includes $832 Premium Upgrades
See more about this car
2021 Toyota Highlander XLE AWD photo
10
Price Drop
Toyota Highlander XLE AWD West Allis, WI
$34,500 36.2k miles
•••

#10 2021 Toyota Highlander

CoPilot AI: It’s anA” Buy

  • $491 Price Drop
  • Good Price - $1,302 Below Market
  • Includes $832 Premium Upgrades
See more about this car
2021 Toyota Highlander XLE AWD photo
11
Price Drop
Toyota Highlander XLE AWD Chicago, IL
$34,790 27.8k miles
•••

#11 2021 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • $100 Price Drop
  • Good Price - $1,767 Below Market
  • 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
Toyota Highlander XSE AWD Palatine, IL
$34,994 46.9k miles
•••

#12 2021 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • $2 Price Drop
  • Good Price - $1,670 Below Market
  • Includes $1,330 Premium Upgrades
See more about this car
2021 Toyota Highlander XLE AWD photo
13
Toyota Highlander XLE AWD Greenfield, WI
$33,875 45.6k miles
•••

#13 2021 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • Good Price - $1,640 Below Market
  • Includes $1,376 Premium Upgrades
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
2021 Toyota Highlander XLE AWD photo
14
Toyota Highlander XLE AWD Northbrook, IL
$34,490 27.1k miles
•••

#14 2021 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • Good Price - $1,605 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
15
Toyota Highlander XLE AWD Bartlett, IL
$34,590 41k miles
•••

#15 2021 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • Good Price - $1,387 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 XLE AWD photo
16
Price Drop
Toyota Highlander XLE AWD Calumet City, IL
$35,273 23.3k miles
•••

#16 2021 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • $100 Price Drop
  • Good Price - $1,311 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
Toyota Highlander XLE AWD Milwaukee, WI
$34,997 31.3k miles
•••

#17 2021 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • Good Price - $1,235 Below Market
  • Includes $559 Premium Upgrades
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
2021 Toyota Highlander LE AWD photo
18
Price Drop
Toyota Highlander LE AWD Streamwood, IL
$31,190 34.1k miles
•••

#18 2021 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • $300 Price Drop
  • Good Price - $1,028 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
Toyota Highlander XSE AWD Milwaukee, WI
$38,113 32.8k miles
•••

#19 2021 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • Fair Price - $761 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 Limited AWD photo
20
Price Drop
Toyota Highlander Limited AWD West Allis, WI
$37,988 38k miles
•••

#20 2021 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • $1,007 Price Drop
  • Fair Price - $728 Below Market
  • Includes $830 Premium Upgrades
See more about this car
2021 Toyota Highlander XLE AWD photo
21
Toyota Highlander XLE AWD West Allis, WI
$34,990 38.5k miles
•••

#21 2021 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • Fair Price - $503 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 XLE AWD photo
22
Toyota Highlander XLE AWD Naperville, IL
$36,377 29.9k miles
•••

#22 2021 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • Fair Price - $498 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 Limited AWD photo
23
Toyota Highlander Limited AWD South Bend, IN
$37,784 39.2k miles
•••

#23 2021 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • Fair Price - $494 Below Market
  • Includes $825 Premium Upgrades
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
2021 Toyota Highlander XLE AWD photo
24
Price Drop
Toyota Highlander XLE AWD South Bend, IN
$36,565 23.5k miles
•••

#24 2021 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • $1,142 Price Drop
  • Fair Price - $433 Below Market
  • Includes $832 Premium Upgrades
See more about this car
2021 Toyota Highlander XLE AWD photo
25
Price Drop
Toyota Highlander XLE AWD Mt Pleasant, WI
$37,490 23.4k miles
•••

#25 2021 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • Fair Price - $431 Below Market
  • Includes $1,391 Premium Upgrades
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
1-25 of 216 results

2021 Toyota Highlander

Mid-size Crossover
Seats
7
Fuel Economy
36 - 36City MPG
35 - 35Hwy MPG
NHTSA Rating Summary
Copilot Rating
Dimensions

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