CoPilot AI-Assisted Car Shopping

 New Search
 Save
 Sort
 Share

Used Toyota Highlander for Sale in Chicago, IL

Highlanders for Sale at Dealers

Filters
Price
Year
Mileage
Trim
2021 Toyota Highlander XLE AWD photo
1
Price Drop
2021 Toyota Highlander XLE AWD • Brookfield, WI
Gray • 3.5L V6 Engine
$37,448 • 29.6k miles • Certified
•••

#1 2015-2023 Toyota Highlander

CoPilot AI: It’s an “A+” Buy

  • $400 Price Drop
  • Great Price - $7,091 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
More details
2022 Toyota Highlander XSE AWD photo
2
Price Drop
2022 Toyota Highlander XSE AWD • Northbrook, IL
Red • 3.5L V6 Engine
$35,990 • 46.2k miles • Certified
•••

#2 2015-2023 Toyota Highlander

CoPilot AI: It’s an “A+” Buy

  • $500 Price Drop
  • Great Price - $6,723 Below Market
  • Includes $1,344 Premium Upgrades
More details
2020 Toyota Highlander L AWD photo
3
Price Drop
2020 Toyota Highlander L AWD • Waukesha, WI
Silver • 3.5L V6 Engine
$25,888 • 45.3k miles
•••

#3 2015-2023 Toyota Highlander

CoPilot AI: It’s an “A+” Buy

  • $1,667 Price Drop
  • Great Price - $3,566 Below Market
  • CARFAX: Clean Title, Not a rental or commercial vehicle
More details
2022 Toyota Highlander XSE AWD photo
4
Price Drop
2022 Toyota Highlander XSE AWD • Milwaukee, WI
Black • 3.5L V6 Engine
$37,983 • 43.8k miles
•••

#4 2015-2023 Toyota Highlander

CoPilot AI: It’s an “A+” Buy

  • $312 Price Drop
  • Great Price - $3,348 Below Market
  • Includes $1,903 Premium Upgrades
More details
2021 Toyota Highlander XSE AWD photo
5
Price Drop
2021 Toyota Highlander XSE AWD • Pleasant Prairie, WI
Blue • 3.5L V6 Engine
$30,000 • 77.1k miles
•••

#5 2015-2023 Toyota Highlander

CoPilot AI: It’s an “A+” Buy

  • $915 Price Drop
  • Great Price - $2,664 Below Market
  • Includes $1,179 Premium Upgrades
More details
2019 Toyota Highlander Limited AWD photo
6
Price Drop
2019 Toyota Highlander Limited AWD • Lincolnwood, IL
Black • 3.5L V6 Engine
$30,488 • 32.1k miles
•••

#6 2015-2023 Toyota Highlander

CoPilot AI: It’s an “A+” Buy

  • $200 Price Drop
  • Great Price - $2,593 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
More details
2021 Toyota Highlander XLE AWD photo
7
Price Drop
2021 Toyota Highlander XLE AWD • Mishawaka, IN
White • 3.5L V6 Engine
$34,388 • 34.2k miles
•••

#7 2015-2023 Toyota Highlander

CoPilot AI: It’s an “A+” Buy

  • $111 Price Drop
  • Great Price - $2,529 Below Market
  • Includes $832 Premium Upgrades
More details
2021 Toyota Highlander LE AWD photo
8
Price Drop
2021 Toyota Highlander LE AWD • Fox Lake, IL
Gold • 3.5L V6 Engine
$30,755 • 30.3k miles
•••

#8 2015-2023 Toyota Highlander

CoPilot AI: It’s an “A+” Buy

  • $54 Price Drop
  • Great Price - $1,979 Below Market
  • Includes $477 Premium Upgrades
More details
2022 Toyota Highlander LE AWD photo
9
Price Drop
2022 Toyota Highlander LE AWD • Michigan City, IN
Black • 3.5L V6 Engine
$29,444 • 29.4k miles
•••

#9 2015-2023 Toyota Highlander

CoPilot AI: It’s an “A+” Buy

  • $555 Price Drop
  • Great Price - $1,908 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
More details
2015 Toyota Highlander Limited Platinum AWD photo
10
Price Drop
2015 Toyota Highlander Limited Platinum AWD • Oconomowoc, WI
Gray • 3.5L V6 Engine
$22,495 • 75.8k miles
•••

#10 2015-2023 Toyota Highlander

CoPilot AI: It’s an “A+” Buy

  • $2,500 Price Drop
  • Great Price - $1,487 Below Market
  • CARFAX: Clean Title, Not a rental or commercial vehicle
More details
2023 Toyota Highlander Platinum FWD photo
11
2023 Toyota Highlander Platinum FWD • Gurnee, IL
Gray • 2.4L I4 Engine
$42,500 • 22.6k miles
•••

#11 2015-2023 Toyota Highlander

CoPilot AI: It’s an “A” Buy

  • Great Price - $4,155 Below Market
  • Includes $479 Premium Upgrades
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
More details
2023 Toyota Highlander LE AWD photo
12
Price Drop
2023 Toyota Highlander LE AWD • Streamwood, IL
Silver • 2.4L I4 Engine
$31,390 • 34.7k miles
•••

#12 2015-2023 Toyota Highlander

CoPilot AI: It’s an “A” Buy

  • $100 Price Drop
  • Great Price - $3,727 Below Market
  • CARFAX: One Owner, Clean Title
More details
2023 Toyota Highlander XLE AWD photo
13
Price Drop
2023 Toyota Highlander XLE AWD • Brookfield, WI
Black • 2.4L I4 Engine
$34,490 • 33.4k miles
•••

#13 2015-2023 Toyota Highlander

CoPilot AI: It’s an “A” Buy

  • $389 Price Drop
  • Great Price - $3,529 Below Market
  • Includes $479 Premium Upgrades
More details
2020 Toyota Highlander Platinum AWD photo
14
Price Drop
2020 Toyota Highlander Platinum AWD • Lincolnwood, IL
Gray • 3.5L V6 Engine
$33,088 • 58.9k miles
•••

#14 2015-2023 Toyota Highlander

CoPilot AI: It’s an “A” Buy

  • $200 Price Drop
  • Great Price - $3,346 Below Market
  • CARFAX: Clean Title, Not a rental or commercial vehicle
More details
2022 Toyota Highlander XLE FWD photo
15
Price Drop
2022 Toyota Highlander XLE FWD • Joliet, IL
Blue • 3.5L V6 Engine
$28,987 • 52.5k miles
•••

#15 2015-2023 Toyota Highlander

CoPilot AI: It’s an “A” Buy

  • $314 Price Drop
  • Great Price - $3,339 Below Market
  • CARFAX: One Owner, Clean Title
More details
2021 Toyota Highlander XLE AWD photo
16
Price Drop
2021 Toyota Highlander XLE AWD • Libertyville, IL
Silver • 3.5L V6 Engine
$29,991 • 50.3k miles
•••

#16 2015-2023 Toyota Highlander

CoPilot AI: It’s an “A” Buy

  • $600 Price Drop
  • Great Price - $3,265 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
More details
2023 Toyota Highlander Limited AWD photo
17
2023 Toyota Highlander Limited AWD • Mishawaka, IN
Blue • 2.4L I4 Engine
$41,999 • 11.3k miles
•••

#17 2015-2023 Toyota Highlander

CoPilot AI: It’s an “A” Buy

  • Great Price - $2,946 Below Market
  • CARFAX: Clean Title, Not a rental or commercial vehicle
  • Very Low Mileage
More details
2022 Toyota Highlander XLE AWD photo
18
Price Drop
2022 Toyota Highlander XLE AWD • Morton Grove, IL
Silver • 3.5L V6 Engine
$32,991 • 38.2k miles
•••

#18 2015-2023 Toyota Highlander

CoPilot AI: It’s an “A” Buy

  • $1,519 Price Drop
  • Great Price - $2,806 Below Market
  • Includes $832 Premium Upgrades
More details
2022 Toyota Highlander XLE FWD photo
19
Price Drop
2022 Toyota Highlander XLE FWD • Lincolnwood, IL
Silver • 3.5L V6 Engine
$29,688 • 50.8k miles
•••

#19 2015-2023 Toyota Highlander

CoPilot AI: It’s an “A” Buy

  • $200 Price Drop
  • Great Price - $2,801 Below Market
  • CARFAX: One Owner, Clean Title
More details
2022 Toyota Highlander XLE AWD photo
20
Price Drop
2022 Toyota Highlander XLE AWD • Hodgkins, IL
Blue • 3.5L V6 Engine
$37,985 • 43.2k miles • Certified
•••

#20 2015-2023 Toyota Highlander

CoPilot AI: It’s an “A” Buy

  • $556 Price Drop
  • Great Price - $2,470 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
More details
2021 Toyota Highlander XSE AWD photo
21
Price Drop
2021 Toyota Highlander XSE AWD • Northbrook, IL
Silver • 3.5L V6 Engine
$34,990 • 43.7k miles
•••

#21 2015-2023 Toyota Highlander

CoPilot AI: It’s an “A” Buy

  • $500 Price Drop
  • Great Price - $2,339 Below Market
  • Includes $1,324 Premium Upgrades
More details
2021 Toyota Highlander Limited AWD photo
22
Price Drop
2021 Toyota Highlander Limited AWD • Milwaukee, WI
Blue • 3.5L V6 Engine
$35,679 • 53.9k miles • Certified
•••

#22 2015-2023 Toyota Highlander

CoPilot AI: It’s an “A” Buy

  • $100 Price Drop
  • Great Price - $2,338 Below Market
  • CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
More details
2022 Toyota Highlander XLE FWD photo
23
Price Drop
2022 Toyota Highlander XLE FWD • Lincolnwood, IL
White • 3.5L V6 Engine
$30,688 • 49.3k miles
•••

#23 2015-2023 Toyota Highlander

CoPilot AI: It’s an “A” Buy

  • $200 Price Drop
  • Great Price - $2,313 Below Market
  • CARFAX: One Owner, Clean Title
More details
2019 Toyota Highlander XLE AWD photo
24
Price Drop
2019 Toyota Highlander XLE AWD • Sycamore, IL
White • 3.5L V6 Engine
$26,777 • 65.3k miles
•••

#24 2015-2023 Toyota Highlander

CoPilot AI: It’s an “A” Buy

  • $200 Price Drop
  • Great Price - $2,288 Below Market
  • CARFAX: Clean Title
More details
2023 Toyota Highlander LE AWD photo
25
Price Drop
2023 Toyota Highlander LE AWD • Streamwood, IL
Blue • 2.4L I4 Engine
$31,390 • 31.4k miles
•••

#25 2015-2023 Toyota Highlander

CoPilot AI: It’s an “A” Buy

  • $100 Price Drop
  • Great Price - $2,261 Below Market
  • CARFAX: One Owner, Clean Title
More details
1-25 of 506 results
HomeToyotaHighlander

2024 Toyota Highlander

Mid-size Crossover
Seats
8
Fuel Economy
35City MPG
35Hwy MPG
NHTSA Rating Summary
Dimensions
Toyota Highlander for Sale by City
Research More Models
View more SUVs

© 2024 CoPilot. All Rights Reserved.