CoPilot AI-Assisted Car Shopping

 New Search
 Save
 Sort
 Share

Used 2021 Toyota Highlander for Sale in Chicago, IL

Highlanders for Sale at Dealers

Filters
Price
Year
Mileage
Trim
2021 Toyota Highlander Platinum AWD photo
Price Drop
2021 Toyota Highlander Platinum AWD Greenfield, WI
Silver 3.5L V6 Engine
$37,994 65.8k miles
•••

#87 2020-2022 Toyota Highlander

CoPilot AI: It’s aD+” Buy

  • $140 Price Drop
  • CARFAX: One Owner
  • Below Average Mileage
More details
2022 Toyota Highlander Hybrid XLE AWD photo
2022 Toyota Highlander Hybrid XLE AWD Naperville, IL
Silver 2.5L I4 Engine
$33,995 103.2k miles
•••

#124 2020-2022 Toyota Highlander

CoPilot AI: It’s aF” Buy

  • CARFAX: One Owner
  • Motivation to Negotiate - Increasing
  • Dealer Rating - 4.8 stars
More details
2022 Toyota Highlander XLE AWD photo
2022 Toyota Highlander XLE AWD Plymouth, IN
Gold 3.5L V6 Engine
$35,637 52.7k miles
•••

#84 2020-2022 Toyota Highlander

CoPilot AI: It’s aD+” Buy

  • Includes $541 Premium Upgrades
  • Motivation to Negotiate - High
  • Below Average Mileage
More details
2021 Toyota Highlander XLE AWD photo
2021 Toyota Highlander XLE AWD Glendale Heights, IL
Silver 3.5L V6 Engine
$29,548 77.2k miles
•••

#58 2020-2022 Toyota Highlander

CoPilot AI: It’s aC+” Buy

  • Fair Price - $114 Below Market
  • Motivation to Negotiate - Increasing
  • Average Mileage
More details
2022 Toyota Highlander XLE AWD photo
2022 Toyota Highlander XLE AWD McHenry, IL
Gold 3.5L V6 Engine
$38,250 28.7k miles
•••

#91 2020-2022 Toyota Highlander

CoPilot AI: It’s aD-” Buy

  • CARFAX: One Owner
  • Very Low Mileage
  • Dealer Rating - 5.0 stars
More details
2022 Toyota Highlander XLE AWD photo
Price Drop
2022 Toyota Highlander XLE AWD Milwaukee, WI
Gray 3.5L V6 Engine
$31,901 81.8k miles
•••

#72 2020-2022 Toyota Highlander

CoPilot AI: It’s aC+” Buy

  • $536 Price Drop
  • Fair Price - $738 Above Market
  • Includes $496 Premium Upgrades
More details
2022 Toyota Highlander Hybrid Platinum AWD photo
2022 Toyota Highlander Hybrid Platinum AWD Milwaukee, WI
Blue 2.5L I4 Engine
$42,463 57.6k miles
•••

#53 2020-2022 Toyota Highlander

CoPilot AI: It’s aC+” Buy

  • Fair Price - $270 Below Market
  • Includes $559 Premium Upgrades
  • CARFAX: One Owner
More details
2021 Toyota Highlander L AWD photo
Price Drop
2021 Toyota Highlander L AWD Palatine, IL
Gray 3.5L V6 Engine
$26,911 65.8k miles
•••

#70 2020-2022 Toyota Highlander

CoPilot AI: It’s aC+” Buy

  • $895 Price Drop
  • Fair Price - $521 Above Market
  • Motivation to Negotiate - Increasing
More details
2021 Toyota Highlander Hybrid XLE AWD photo
Price Drop
2021 Toyota Highlander Hybrid XLE AWD Arlington Heights, IL
Black 2.5L I4 Engine
$22,495 166.7k miles
•••

#40 2020-2022 Toyota Highlander

CoPilot AI: It’s aC+” Buy

  • $500 Price Drop
  • Good Price - $830 Below Market
  • Motivation to Negotiate - Increasing
More details
2021 Toyota Highlander Hybrid Platinum AWD photo
2021 Toyota Highlander Hybrid Platinum AWD Dixon, IL
White 2.5L I4 Engine
$35,995 95.4k miles
•••

#111 2020-2022 Toyota Highlander

CoPilot AI: It’s aF” Buy

  • Dealer Rating - 4.6 stars
More details
2020 Toyota Highlander Hybrid XLE AWD photo
2020 Toyota Highlander Hybrid XLE AWD Palatine, IL
Gray 2.5L I4 Engine
$28,701 115.3k miles
•••

#68 2020-2022 Toyota Highlander

CoPilot AI: It’s aC+” Buy

  • Fair Price - $477 Above Market
  • Dealer Rating - 4.6 stars
More details
2022 Toyota Highlander XLE AWD photo
2022 Toyota Highlander XLE AWD Schaumburg, IL
Red 3.5L V6 Engine
$35,334 44.1k miles
•••

#76 2020-2022 Toyota Highlander

CoPilot AI: It’s aC-” Buy

  • CARFAX: One Owner
  • Very Low Mileage
  • Dealer Rating - 4.6 stars
More details
2022 Toyota Highlander Platinum AWD photo
2022 Toyota Highlander Platinum AWD Gurnee, IL
White 3.5L V6 Engine
$33,934 106.1k miles
•••

#74 2020-2022 Toyota Highlander

CoPilot AI: It’s aC” Buy

  • Fair Price - $301 Above Market
  • CARFAX: One Owner
  • Dealer Rating - 4.3 stars
More details
2022 Toyota Highlander XLE AWD photo
13
2022 Toyota Highlander XLE AWD Calumet City, IL
White 3.5L V6 Engine
$35,574 42.9k miles
•••

#13 2020-2022 Toyota Highlander

CoPilot AI: It’s aB” Buy

  • Good Price - $1,630 Below Market
  • Includes $556 Premium Upgrades
  • CARFAX: One Owner
More details
2021 Toyota Highlander Hybrid Platinum AWD photo
2021 Toyota Highlander Hybrid Platinum AWD Ottawa, IL
Gray 2.5L I4 Engine
$36,597 77k miles
•••

#60 2020-2022 Toyota Highlander

CoPilot AI: It’s aC+” Buy

  • Fair Price - $58 Below Market
  • CARFAX: One Owner
  • Average Mileage
More details
2022 Toyota Highlander XLE AWD photo
Price Drop
2022 Toyota Highlander XLE AWD Elkhart, IN
Gray 3.5L V6 Engine
$29,773 95.4k miles
•••

#69 2020-2022 Toyota Highlander

CoPilot AI: It’s aC+” Buy

  • $227 Price Drop
  • Fair Price - $480 Above Market
  • Motivation to Negotiate - Very High
More details
2020 Toyota Highlander Hybrid LE AWD photo
2020 Toyota Highlander Hybrid LE AWD McHenry, IL
Gray 2.5L I4 Engine
$27,999
•••
More details
2021 Toyota Highlander XLE AWD photo
2021 Toyota Highlander XLE AWD Burbank, IL
Blue 3.5L V6 Engine
$29,995 85.6k miles
•••

#67 2020-2022 Toyota Highlander

CoPilot AI: It’s aC+” Buy

  • Fair Price - $477 Above Market
  • CARFAX: One Owner
  • Motivation to Negotiate - Very High
More details
2021 Toyota Highlander XSE AWD photo
2021 Toyota Highlander XSE AWD Waukesha, WI
Black 3.5L V6 Engine
$34,999 59.4k miles
•••

#99 2020-2022 Toyota Highlander

CoPilot AI: It’s aD-” Buy

  • Below Average Mileage
More details
2021 Toyota Highlander LE AWD photo
2021 Toyota Highlander LE AWD Palos Hills, IL
Silver 3.5L V6 Engine
$22,995 110.9k miles
•••

#71 2020-2022 Toyota Highlander

CoPilot AI: It’s aC+” Buy

  • Fair Price - $607 Above Market
  • Dealer Rating - 4.1 stars
More details
2022 Toyota Highlander Limited AWD photo
10
Price Drop
2022 Toyota Highlander Limited AWD Highland, IN
White 3.5L V6 Engine
$33,436 67k miles
•••

#10 2020-2022 Toyota Highlander

CoPilot AI: It’s aB” Buy

  • $300 Price Drop
  • Good Price - $2,132 Below Market
  • Includes $1,244 Premium Upgrades
More details
2021 Toyota Highlander XLE AWD photo
Price Drop
2021 Toyota Highlander XLE AWD Waukesha, WI
Gray 3.5L V6 Engine
$27,185 100.7k miles
•••

#41 2020-2022 Toyota Highlander

CoPilot AI: It’s aC+” Buy

  • $213 Price Drop
  • Fair Price - $681 Below Market
  • Motivation to Negotiate - Increasing
More details
2021 Toyota Highlander XLE AWD photo
12
Price Drop
2021 Toyota Highlander XLE AWD Mishawaka, IN
Blue 3.5L V6 Engine
$31,151 63.8k miles
•••

#12 2020-2022 Toyota Highlander

CoPilot AI: It’s aB” Buy

  • $103 Price Drop
  • Good Price - $1,748 Below Market
  • Includes $766 Premium Upgrades
More details
2021 Toyota Highlander XLE AWD photo
2021 Toyota Highlander XLE AWD Chicago, IL
Gray 3.5L V6 Engine
$26,299 126.5k miles
•••

#43 2020-2022 Toyota Highlander

CoPilot AI: It’s aC+” Buy

  • Fair Price - $632 Below Market
  • Includes $1,033 Premium Upgrades
  • CARFAX: One Owner
More details
2022 Toyota Highlander Platinum AWD photo
2022 Toyota Highlander Platinum AWD Schaumburg, IL
White 3.5L V6 Engine
$49,312 22k miles
•••

#102 2020-2022 Toyota Highlander

CoPilot AI: It’s aD-” Buy

  • CARFAX: One Owner
  • Very Low Mileage
  • Dealer Rating - 4.6 stars
More details
1-25 of 151 results

2021 Toyota Highlander

Mid-size Crossover
Seats
8
Fuel Economy
36City MPG
35Hwy MPG
NHTSA Rating Summary
Copilot Rating
Dimensions
Most Popular Models like Highlander
Other Years
Research More Models
View more SUVs

© 2026 CoPilot. All Rights Reserved.