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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
2021 Toyota Highlander XSE AWD Milwaukee, WI
$36,490 27.4k miles
•••

#1 2021 Toyota Highlander

CoPilot AI: It’s anA+” Buy

  • $501 Price Drop
  • Great Price - $3,267 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 2021 Toyota Highlander

CoPilot AI: It’s anA+” Buy

  • Great Price - $2,193 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 2021 Toyota Highlander

CoPilot AI: It’s anA+” Buy

  • Great Price - $4,441 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 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
2021 Toyota Highlander Hybrid Platinum AWD photo
5
Price Drop
2021 Toyota Highlander Hybrid Platinum AWD Gurnee, IL
$38,225 57.2k miles
•••

#5 2021 Toyota Highlander

CoPilot AI: It’s anA” Buy

  • $701 Price Drop
  • Great Price - $2,678 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
2021 Toyota Highlander XLE AWD photo
6
Price Drop
2021 Toyota Highlander XLE AWD South Bend, IN
$33,006 49k miles
•••

#6 2021 Toyota Highlander

CoPilot AI: It’s anA” Buy

  • $425 Price Drop
  • Great Price - $2,637 Below Market
  • Includes $820 Premium Upgrades
See more about this car
2021 Toyota Highlander Limited FWD photo
7
Price Drop
2021 Toyota Highlander Limited FWD Milwaukee, WI
$36,995 19.8k miles
•••

#7 2021 Toyota Highlander

CoPilot AI: It’s anA” Buy

  • $62 Price Drop
  • Good Price - $2,295 Below Market
  • Includes $1,054 Premium Upgrades
See more about this car
2021 Toyota Highlander XLE AWD photo
8
Price Drop
2021 Toyota Highlander XLE AWD Chicago, IL
$35,732 23.1k miles
•••

#8 2021 Toyota Highlander

CoPilot AI: It’s anA” Buy

  • $42 Price Drop
  • Good Price - $2,050 Below Market
  • Includes $1,311 Premium Upgrades
See more about this car
2021 Toyota Highlander XSE AWD photo
9
Price Drop
2021 Toyota Highlander XSE AWD Brookfield, WI
$36,200 38.3k miles
•••

#9 2021 Toyota Highlander

CoPilot AI: It’s anA” Buy

  • $300 Price Drop
  • Good Price - $2,047 Below Market
  • Includes $1,344 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 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 2021 Toyota Highlander

CoPilot AI: It’s anA” Buy

  • Good Price - $1,734 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 Milwaukee, WI
$37,588 32.8k miles
•••

#12 2021 Toyota Highlander

CoPilot AI: It’s anA” Buy

  • $407 Price Drop
  • Good Price - $1,339 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 2021 Toyota Highlander

CoPilot AI: It’s anA” Buy

  • $280 Price Drop
  • Good Price - $1,194 Below Market
  • Includes $832 Premium Upgrades
See more about this car
2021 Toyota Highlander XLE AWD photo
14
2021 Toyota Highlander XLE AWD Romeoville, IL
$35,000 28.4k miles
•••

#14 2021 Toyota Highlander

CoPilot AI: It’s anA” Buy

  • Good Price - $1,108 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
15
Price Drop
2021 Toyota Highlander XLE AWD South Bend, IN
$35,420 27.7k miles
•••

#15 2021 Toyota Highlander

CoPilot AI: It’s anA” Buy

  • $797 Price Drop
  • Good Price - $1,108 Below Market
  • Includes $832 Premium Upgrades
See more about this car
2021 Toyota Highlander LE AWD photo
16
Price Drop
2021 Toyota Highlander LE AWD Oak Lawn, IL
$29,900 35.7k miles
•••

#16 2021 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • $100 Price Drop
  • Good Price - $1,718 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 Northbrook, IL
$33,990 37.7k miles
•••

#17 2021 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • $500 Price Drop
  • Good Price - $1,682 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
2021 Toyota Highlander XLE AWD photo
18
2021 Toyota Highlander XLE AWD Milwaukee, WI
$33,950 45.6k miles
•••

#18 2021 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • Good Price - $1,647 Below Market
  • Includes $1,379 Premium Upgrades
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
2021 Toyota Highlander XLE AWD photo
19
Price Drop
2021 Toyota Highlander XLE AWD North Aurora, IL
$35,999 17.5k miles
•••

#19 2021 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • $1,000 Price Drop
  • Good Price - $1,597 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
2021 Toyota Highlander XLE AWD photo
20
2021 Toyota Highlander XLE AWD Streamwood, IL
$33,990 34.5k miles
•••

#20 2021 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • Good Price - $1,584 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
21
Price Drop
2021 Toyota Highlander XLE AWD Northbrook, IL
$34,490 27.1k miles
•••

#21 2021 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • $500 Price Drop
  • Good Price - $1,556 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
2021 Toyota Highlander XLE AWD photo
22
2021 Toyota Highlander XLE AWD Chicago, IL
$34,990 27.8k miles
•••

#22 2021 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • Good Price - $1,524 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
23
Price Drop
2021 Toyota Highlander XLE AWD Calumet City, IL
$35,373 23.3k miles
•••

#23 2021 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • $100 Price Drop
  • Good Price - $1,133 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
Price Drop
2021 Toyota Highlander XLE AWD Milwaukee, WI
$31,797 73.2k miles
•••

#24 2021 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • $542 Price Drop
  • Good Price - $988 Below Market
  • Includes $771 Premium Upgrades
See more about this car
2021 Toyota Highlander XLE AWD photo
25
2021 Toyota Highlander XLE AWD Tinley Park, IL
$35,299 31.4k miles
•••

#25 2021 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • Fair Price - $920 Below Market
  • Includes $832 Premium Upgrades
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
1-25 of 205 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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