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
2022 Toyota Highlander XLE AWD photo
1
2022 Toyota Highlander XLE AWD Chicago, IL
Silver 3.5L V6 Engine
$35,995 21.9k miles
•••

#1 2020-2022 Toyota Highlander

CoPilot AI: It’s anA+” Buy

  • Great Price - $4,051 Below Market
  • Includes $559 Premium Upgrades
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
More details
2021 Toyota Highlander XLE AWD photo
2
Price Drop
2021 Toyota Highlander XLE AWD Elmhurst, IL
Red 3.5L V6 Engine
$32,750 30.5k miles
•••

#2 2020-2022 Toyota Highlander

CoPilot AI: It’s anA+” Buy

  • $485 Price Drop
  • Great Price - $2,765 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
More details
2022 Toyota Highlander XLE AWD photo
3
Price Drop
2022 Toyota Highlander XLE AWD Mishawaka, IN
Gray 3.5L V6 Engine
$34,608 42.1k miles
•••

#3 2020-2022 Toyota Highlander

CoPilot AI: It’s anA+” Buy

  • $349 Price Drop
  • Great Price - $2,712 Below Market
  • Includes $832 Premium Upgrades
More details
2020 Toyota Highlander LE FWD photo
4
Price Drop
2020 Toyota Highlander LE FWD Mishawaka, IN
White 3.5L V6 Engine
$25,454 51.3k miles
•••

#4 2020-2022 Toyota Highlander

CoPilot AI: It’s anA” Buy

  • $437 Price Drop
  • Great Price - $6,640 Below Market
  • Includes $487 Premium Upgrades
More details
2022 Toyota Highlander XLE FWD photo
5
Price Drop
2022 Toyota Highlander XLE FWD Elmhurst, IL
Silver 3.5L V6 Engine
$31,626 34k miles
•••

#5 2020-2022 Toyota Highlander

CoPilot AI: It’s anA” Buy

  • $700 Price Drop
  • Great Price - $3,454 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
More details
2020 Toyota Highlander XLE AWD photo
6
2020 Toyota Highlander XLE AWD Bourbonnais, IL
Red 3.5L V6 Engine
$25,795 81k miles
•••

#6 2020-2022 Toyota Highlander

CoPilot AI: It’s anA” Buy

  • Great Price - $3,155 Below Market
  • Includes $452 Premium Upgrades
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
More details
2022 Toyota Highlander XLE AWD photo
7
Price Drop
2022 Toyota Highlander XLE AWD Schererville, IN
Gray 3.5L V6 Engine
$34,000 45.7k miles
•••

#7 2020-2022 Toyota Highlander

CoPilot AI: It’s anA” Buy

  • $400 Price Drop
  • Great Price - $2,270 Below Market
  • CARFAX: One Owner, Clean Title
More details
2022 Toyota Highlander XSE AWD photo
8
2022 Toyota Highlander XSE AWD Bourbonnais, IL
Black 3.5L V6 Engine
$38,498 26.5k miles Certified
•••

#8 2020-2022 Toyota Highlander

CoPilot AI: It’s anA” Buy

  • Good Price - $2,190 Below Market
  • Includes $1,903 Premium Upgrades
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
More details
2021 Toyota Highlander Hybrid Limited AWD photo
9
Price Drop
2021 Toyota Highlander Hybrid Limited AWD Tinley Park, IL
Black 2.5L I4 Engine
$41,999 40.7k miles
•••

#9 2020-2022 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • $2,300 Price Drop
  • Great Price - $2,950 Below Market
  • CARFAX: Clean Title, Not a rental or commercial vehicle
More details
2021 Toyota Highlander XLE AWD photo
10
Price Drop
2021 Toyota Highlander XLE AWD Streamwood, IL
Silver 3.5L V6 Engine
$28,990 70.3k miles
•••

#10 2020-2022 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • $300 Price Drop
  • Great Price - $2,056 Below Market
  • CARFAX: Clean Title
More details
2022 Toyota Highlander Hybrid XLE AWD photo
11
Price Drop
2022 Toyota Highlander Hybrid XLE AWD Milwaukee, WI
White 2.5L I4 Engine
$41,699 25.5k miles
•••

#11 2020-2022 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • $192 Price Drop
  • Good Price - $1,780 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
More details
2022 Toyota Highlander XLE AWD photo
12
Price Drop
2022 Toyota Highlander XLE AWD Mishawaka, IN
Gray 3.5L V6 Engine
$33,043 56.2k miles
•••

#12 2020-2022 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • $447 Price Drop
  • Good Price - $1,603 Below Market
  • Includes $804 Premium Upgrades
More details
2021 Toyota Highlander XLE AWD photo
13
Price Drop
2021 Toyota Highlander XLE AWD Merrillville, IN
Red 3.5L V6 Engine
$32,196 35.5k miles Certified
•••

#13 2020-2022 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • $501 Price Drop
  • Good Price - $1,527 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
More details
2020 Toyota Highlander Limited AWD photo
14
Price Drop
2020 Toyota Highlander Limited AWD Schererville, IN
Gray 3.5L V6 Engine
$34,000 28.4k miles Certified
•••

#14 2020-2022 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • $800 Price Drop
  • Good Price - $1,289 Below Market
  • Includes $404 Premium Upgrades
More details
2021 Toyota Highlander XSE AWD photo
15
Price Drop
2021 Toyota Highlander XSE AWD Brookfield, WI
Red 3.5L V6 Engine
$34,704 30.2k miles
•••

#15 2020-2022 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • $825 Price Drop
  • Good Price - $1,282 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
More details
2020 Toyota Highlander Limited AWD photo
16
Price Drop
2020 Toyota Highlander Limited AWD West Allis, WI
Red 3.5L V6 Engine
$28,995 89.1k miles
•••

#16 2020-2022 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • $500 Price Drop
  • Good Price - $1,251 Below Market
  • Includes $651 Premium Upgrades
More details
2021 Toyota Highlander XSE AWD photo
17
Price Drop
2021 Toyota Highlander XSE AWD Lisle, IL
White 3.5L V6 Engine
$35,621 36.5k miles
•••

#17 2020-2022 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • $50 Price Drop
  • Fair Price - $832 Below Market
  • Includes $1,293 Premium Upgrades
More details
2022 Toyota Highlander Hybrid XLE AWD photo
18
Price Drop
2022 Toyota Highlander Hybrid XLE AWD Matteson, IL
Silver 2.5L I4 Engine
$42,389 22.4k miles Certified
•••

#18 2020-2022 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • $91 Price Drop
  • Fair Price - $267 Below Market
  • Includes $832 Premium Upgrades
More details
2022 Toyota Highlander Hybrid Platinum AWD photo
19
Price Drop
2022 Toyota Highlander Hybrid Platinum AWD Park Ridge, IL
Gray 2.5L I4 Engine
$50,991 22.1k miles Certified
•••

#19 2020-2022 Toyota Highlander

CoPilot AI: It’s anA-” Buy

  • $2,000 Price Drop
  • Fair Price - $912 Above Market
  • Includes $1,038 Premium Upgrades
More details
2021 Toyota Highlander XLE AWD photo
20
Price Drop
2021 Toyota Highlander XLE AWD Aurora, IL
Gray 3.5L V6 Engine
$28,495 90.5k miles
•••

#20 2020-2022 Toyota Highlander

CoPilot AI: It’s aB+” Buy

  • $500 Price Drop
  • Great Price - $8,134 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
More details
2021 Toyota Highlander XSE AWD photo
21
2021 Toyota Highlander XSE AWD Naperville, IL
Gray 3.5L V6 Engine
$32,555 75.5k miles Certified
•••

#21 2020-2022 Toyota Highlander

CoPilot AI: It’s aB+” Buy

  • Great Price - $7,094 Below Market
  • Includes $1,150 Premium Upgrades
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
More details
2022 Toyota Highlander XLE AWD photo
22
Price Drop
2022 Toyota Highlander XLE AWD Lincolnwood, IL
3.5L V6 Engine
$34,850 37.7k miles
•••

#22 2020-2022 Toyota Highlander

CoPilot AI: It’s aB+” Buy

  • $150 Price Drop
  • Great Price - $5,832 Below Market
  • CARFAX: One Owner, Clean Title
More details
2021 Toyota Highlander XLE FWD photo
23
Price Drop
2021 Toyota Highlander XLE FWD Oak Forest, IL
Black 3.5L V6 Engine
$25,980 73k miles
•••

#23 2020-2022 Toyota Highlander

CoPilot AI: It’s aB+” Buy

  • $1,000 Price Drop
  • Great Price - $4,899 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
More details
2021 Toyota Highlander XLE AWD photo
24
Price Drop
2021 Toyota Highlander XLE AWD Huntley, IL
Silver 3.5L V6 Engine
$25,872 88.2k miles
•••

#24 2020-2022 Toyota Highlander

CoPilot AI: It’s aB+” Buy

  • $500 Price Drop
  • Great Price - $4,224 Below Market
  • Includes $707 Premium Upgrades
More details
2022 Toyota Highlander XLE AWD photo
25
Price Drop
2022 Toyota Highlander XLE AWD Naperville, IL
Gray 3.5L V6 Engine
$31,988 43.1k miles
•••

#25 2020-2022 Toyota Highlander

CoPilot AI: It’s aB+” Buy

  • $500 Price Drop
  • Great Price - $3,632 Below Market
  • Includes $832 Premium Upgrades
More details
1-25 of 209 results

2021 Toyota Highlander

Mid-size Crossover
Seats
8
Fuel Economy
20City MPG
27Hwy MPG
NHTSA Rating Summary
Dimensions
Most Popular Models like Highlander
Other Years
Research More Models
View more SUVs

© 2024 CoPilot. All Rights Reserved.