New Search
Save
Sort
Share
Used 2019 Toyota Highlander for Sale in Chicago, IL
Highlanders for Sale at Dealers
Filters
Price
Year
Mileage
Trim
1
Price Drop
2020 Toyota Highlander LE FWD • Mishawaka, IN
White • 3.5L V6 Engine
White • 3.5L V6 Engine
$25,690 • 51.3k miles
•••
#1 2017-2021 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- $154 Price Drop
- Great Price - $6,084 Below Market
- Includes $482 Premium Upgrades
More details
2
Price Drop
2019 Toyota Highlander LE FWD • Kenosha, WI
Gray • 3.5L V6 Engine
Gray • 3.5L V6 Engine
$23,185 • 67.6k miles
•••
#2 2017-2021 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- $1,492 Price Drop
- Great Price - $2,873 Below Market
- Includes $345 Premium Upgrades
More details
3
2021 Toyota Highlander XLE FWD • Calumet City, IL
Gray • 3.5L V6 Engine
Gray • 3.5L V6 Engine
$29,939 • 65.1k miles
•••
#3 2017-2021 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- Great Price - $2,513 Below Market
- Includes $1,078 Premium Upgrades
- CARFAX: Clean Title
More details
4
Price Drop
2021 Toyota Highlander XLE AWD • Berwyn, IL
Gold • 3.5L V6 Engine
Gold • 3.5L V6 Engine
$28,750 • 68.3k miles
•••
#4 2017-2021 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- $1,000 Price Drop
- Great Price - $2,435 Below Market
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
More details
5
Price Drop
2020 Toyota Highlander XLE AWD • Bourbonnais, IL
Red • 3.5L V6 Engine
Red • 3.5L V6 Engine
$26,795 • 81k miles
•••
#5 2017-2021 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- $100 Price Drop
- Great Price - $2,140 Below Market
- Includes $451 Premium Upgrades
More details
6
Price Drop
2021 Toyota Highlander XLE AWD • Bourbonnais, IL
Red • 3.5L V6 Engine
Red • 3.5L V6 Engine
$30,998 • 60.2k miles • Certified
•••
#6 2017-2021 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- $500 Price Drop
- Great Price - $2,127 Below Market
- Includes $769 Premium Upgrades
More details
7
Price Drop
2021 Toyota Highlander XSE AWD • Lisle, IL
White • 3.5L V6 Engine
White • 3.5L V6 Engine
$35,446 • 36.5k miles
•••
#7 2017-2021 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- $25 Price Drop
- Good Price - $1,868 Below Market
- Includes $1,323 Premium Upgrades
More details
8
Price Drop
2021 Toyota Highlander XLE AWD • Libertyville, IL
Silver • 3.5L V6 Engine
Silver • 3.5L V6 Engine
$34,795 • 25.6k miles • Certified
•••
#8 2017-2021 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- $200 Price Drop
- Good Price - $1,733 Below Market
- Includes $832 Premium Upgrades
More details
9
2021 Toyota Highlander XLE AWD • Mishawaka, IN
Gray • 3.5L V6 Engine
Gray • 3.5L V6 Engine
$34,599 • 28.2k miles
•••
#9 2017-2021 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- Good Price - $1,431 Below Market
- Includes $832 Premium Upgrades
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
More details
10
Price Drop
2021 Toyota Highlander Hybrid Limited AWD • Tinley Park, IL
Black • 2.5L I4 Engine
Black • 2.5L I4 Engine
$41,999 • 40.7k miles
•••
#10 2017-2021 Toyota Highlander
CoPilot AI: It’s an “A-” Buy
- $2,300 Price Drop
- Great Price - $3,012 Below Market
- CARFAX: Clean Title, Not a rental or commercial vehicle
More details
11
Price Drop
2021 Toyota Highlander XLE AWD • Streamwood, IL
Silver • 3.5L V6 Engine
Silver • 3.5L V6 Engine
$28,490 • 70.3k miles
•••
#11 2017-2021 Toyota Highlander
CoPilot AI: It’s an “A-” Buy
- $300 Price Drop
- Great Price - $2,384 Below Market
- CARFAX: Clean Title
More details
12
Price Drop
2021 Toyota Highlander XLE AWD • Lincolnwood, IL
Black • 3.5L V6 Engine
Black • 3.5L V6 Engine
$30,456 • 64.2k miles
•••
#12 2017-2021 Toyota Highlander
CoPilot AI: It’s an “A-” Buy
- $498 Price Drop
- Good Price - $1,746 Below Market
- Includes $760 Premium Upgrades
More details
13
Price Drop
2021 Toyota Highlander XSE AWD • Naperville, IL
Gray • 3.5L V6 Engine
Gray • 3.5L V6 Engine
$34,257 • 46.9k miles
•••
#13 2017-2021 Toyota Highlander
CoPilot AI: It’s an “A-” Buy
- $441 Price Drop
- Good Price - $1,308 Below Market
- Includes $1,280 Premium Upgrades
More details
14
2020 Toyota Highlander LE AWD • Ottawa, IL
Black • 3.5L V6 Engine
Black • 3.5L V6 Engine
$28,995 • 27.5k miles
•••
#14 2017-2021 Toyota Highlander
CoPilot AI: It’s an “A-” Buy
- Good Price - $1,068 Below Market
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
- Very Low Mileage
More details
15
Price Drop
2019 Toyota Highlander XLE AWD • Elmhurst, IL
Black • 3.5L V6 Engine
Black • 3.5L V6 Engine
$29,800 • 27.8k miles
•••
#15 2017-2021 Toyota Highlander
CoPilot AI: It’s an “A-” Buy
- $550 Price Drop
- Good Price - $928 Below Market
- CARFAX: Clean Title
More details
16
2021 Toyota Highlander Hybrid Limited AWD • Fox Lake, IL
White • 2.5L I4 Engine
White • 2.5L I4 Engine
$42,000 • 21.9k miles
•••
#16 2017-2021 Toyota Highlander
CoPilot AI: It’s an “A-” Buy
- Fair Price - $697 Below Market
- Includes $840 Premium Upgrades
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
More details
17
2021 Toyota Highlander XLE AWD • West Allis, WI
Gray • 3.5L V6 Engine
Gray • 3.5L V6 Engine
$35,995 • 36k miles
•••
#17 2017-2021 Toyota Highlander
CoPilot AI: It’s an “A-” Buy
- Fair Price - $613 Above Market
- Includes $831 Premium Upgrades
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
More details
18
Price Drop
2021 Toyota Highlander XLE AWD • Aurora, IL
Gray • 3.5L V6 Engine
Gray • 3.5L V6 Engine
$27,995 • 90.5k miles
•••
#18 2017-2021 Toyota Highlander
CoPilot AI: It’s a “B+” Buy
- $500 Price Drop
- Great Price - $8,291 Below Market
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
More details
19
2021 Toyota Highlander XSE AWD • Naperville, IL
Gray • 3.5L V6 Engine
Gray • 3.5L V6 Engine
$32,555 • 75.5k miles • Certified
•••
#19 2017-2021 Toyota Highlander
CoPilot AI: It’s a “B+” Buy
- Great Price - $7,514 Below Market
- Includes $1,162 Premium Upgrades
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
More details
20
Price Drop
2021 Toyota Highlander XLE FWD • Oak Forest, IL
Black • 3.5L V6 Engine
Black • 3.5L V6 Engine
$25,980 • 73k miles
•••
#20 2017-2021 Toyota Highlander
CoPilot AI: It’s a “B+” Buy
- $1,000 Price Drop
- Great Price - $5,909 Below Market
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
More details
21
Price Drop
2018 Toyota Highlander XLE AWD • Lockport, IL
3.5L V6 Engine
3.5L V6 Engine
$21,499 • 105k miles
•••
#21 2017-2021 Toyota Highlander
CoPilot AI: It’s a “B+” Buy
- $496 Price Drop
- Great Price - $4,227 Below Market
- CARFAX: Clean Title
More details
22
Price Drop
2021 Toyota Highlander XLE AWD • Huntley, IL
Silver • 3.5L V6 Engine
Silver • 3.5L V6 Engine
$25,871 • 88.2k miles
•••
#22 2017-2021 Toyota Highlander
CoPilot AI: It’s a “B+” Buy
- $1 Price Drop
- Great Price - $3,953 Below Market
- Includes $701 Premium Upgrades
More details
23
Price Drop
2020 Toyota Highlander LE AWD • Joliet, IL
Black • 3.5L V6 Engine
Black • 3.5L V6 Engine
$21,000 • 97.9k miles
•••
#23 2017-2021 Toyota Highlander
CoPilot AI: It’s a “B+” Buy
- $2,343 Price Drop
- Great Price - $3,836 Below Market
- CARFAX: Clean Title
More details
24
Price Drop
2017 Toyota Highlander Limited Platinum AWD • Naperville, IL
3.5L V6 Engine
3.5L V6 Engine
$21,998 • 95.2k miles
•••
#24 2017-2021 Toyota Highlander
CoPilot AI: It’s a “B+” Buy
- $1,993 Price Drop
- Great Price - $3,395 Below Market
- Includes $774 Premium Upgrades
More details
25
2018 Toyota Highlander Limited AWD • Michigan City, IN
Silver • 3.5L V6 Engine
Silver • 3.5L V6 Engine
$26,477 • 80.8k miles
•••
#25 2017-2021 Toyota Highlander
CoPilot AI: It’s a “B+” Buy
- Great Price - $2,886 Below Market
- Includes $146 Premium Upgrades
- CARFAX: Clean Title, Not a rental or commercial vehicle
More details
2019 Toyota Highlander
Mid-size Crossover
Seats
8
Fuel Economy
20City MPG
24Hwy MPG
NHTSA Rating Summary
Copilot Rating
Dimensions
Most Popular Models like HighlanderOther YearsResearch More ModelsView more SUVs