New Search
Save
Sort
Share
Used Toyota Highlander for Sale in Chicago, IL
Highlanders for Sale at Dealers
Filters
Price
Year
Mileage
Trim
Price Drop
2023 Toyota Highlander XSE FWD • Naperville, IL
Black • 2.4L I4 Engine
Black • 2.4L I4 Engine
$38,500 • 41.1k miles • Certified
•••
#160 2015-2023 Toyota Highlander
CoPilot AI: It’s a “B-” Buy
- $524 Price Drop
- Fair Price - $896 Above Market
- Includes $1,100 Premium Upgrades
More details
2022 Toyota Highlander XLE AWD • Milton, WI
Blue • 3.5L V6 Engine
Blue • 3.5L V6 Engine
$33,979 • 42.9k miles
•••
#126 2015-2023 Toyota Highlander
CoPilot AI: It’s a “B-” Buy
- Fair Price - $420 Below Market
- Very Low Mileage
- Dealer Rating - 4.9 stars
More details
Price Drop
2021 Toyota Highlander Hybrid Limited AWD • Waukesha, WI
Red • 2.5L I4 Engine
Red • 2.5L I4 Engine
$34,996 • 77k miles
•••
#332 2015-2023 Toyota Highlander
CoPilot AI: It’s a “F” Buy
- $1,002 Price Drop
- CARFAX: One Owner
- Motivation to Negotiate - Increasing
More details
15
2021 Toyota Highlander XLE AWD • Palos Hills, IL
Blue • 3.5L V6 Engine
Blue • 3.5L V6 Engine
$23,995 • 107.2k miles
•••
#15 2015-2023 Toyota Highlander
CoPilot AI: It’s a “B+” Buy
- Great Price - $2,849 Below Market
- Includes $638 Premium Upgrades
- CARFAX: One Owner
More details
Price Drop
2019 Toyota Highlander LE AWD • Waukegan, IL
Silver • 3.5L V6 Engine
Silver • 3.5L V6 Engine
$18,999 • 104.9k miles
•••
#102 2015-2023 Toyota Highlander
CoPilot AI: It’s a “B-” Buy
- $500 Price Drop
- Good Price - $938 Below Market
- Motivation to Negotiate - Very High
More details
2015 Toyota Highlander LE FWD • Milwaukee, WI
Black • 2.7L I4 Engine
Black • 2.7L I4 Engine
$11,995 • 186.5k miles
•••
#122 2015-2023 Toyota Highlander
CoPilot AI: It’s a “B-” Buy
- Good Price - $566 Below Market
- Motivation to Negotiate - Increasing
More details
2016 Toyota Highlander LE Plus AWD • Milwaukee, WI
White • 3.5L V6 Engine
White • 3.5L V6 Engine
$22,998 • 91.7k miles
•••
#306 2015-2023 Toyota Highlander
CoPilot AI: It’s a “D-” Buy
- CARFAX: One Owner
- Very Low Mileage
- Dealer Rating - 4.2 stars
More details
2015 Toyota Highlander XLE AWD • Roselle, IL
Green • 3.5L V6 Engine
Green • 3.5L V6 Engine
$17,995 • 108.5k miles
•••
#69 2015-2023 Toyota Highlander
CoPilot AI: It’s a “B” Buy
- Good Price - $995 Below Market
- Motivation to Negotiate - Increasing
- Below Average Mileage
More details
Price Drop
2023 Toyota Highlander LE FWD • Kenosha, WI
Gray • 2.4L I4 Engine
Gray • 2.4L I4 Engine
$29,990 • 46.8k miles • Certified
•••
#295 2015-2023 Toyota Highlander
CoPilot AI: It’s a “D” Buy
- $1,000 Price Drop
- Motivation to Negotiate - Increasing
- Average Mileage
More details
Price Drop
2018 Toyota Highlander XLE AWD • Countryside, IL
Gray • 3.5L V6 Engine
Gray • 3.5L V6 Engine
$22,999 • 76.9k miles
•••
#58 2015-2023 Toyota Highlander
CoPilot AI: It’s a “B” Buy
- $124 Price Drop
- Good Price - $1,349 Below Market
- Includes $145 Premium Upgrades
More details
Price Drop
2023 Toyota Highlander L AWD • Lincolnwood, IL
2.4L I4 Engine
2.4L I4 Engine
$32,599 • 32k miles
•••
#112 2015-2023 Toyota Highlander
CoPilot AI: It’s a “B-” Buy
- $200 Price Drop
- Fair Price - $832 Below Market
- CARFAX: One Owner
More details
Price Drop
2022 Toyota Highlander XLE AWD • Chicago, IL
Black • 3.5L V6 Engine
Black • 3.5L V6 Engine
$31,990 • 57.7k miles
•••
#167 2015-2023 Toyota Highlander
CoPilot AI: It’s a “C+” Buy
- $500 Price Drop
- Fair Price - $911 Below Market
- Motivation to Negotiate - Very High
More details
Price Drop
2023 Toyota Highlander LE FWD • Ottawa, IL
Blue • 2.4L I4 Engine
Blue • 2.4L I4 Engine
$30,364 • 34.2k miles
•••
#53 2015-2023 Toyota Highlander
CoPilot AI: It’s a “B” Buy
- $1,030 Price Drop
- Good Price - $1,596 Below Market
- CARFAX: One Owner
More details
Price Drop
2022 Toyota Highlander Hybrid Limited AWD • Lombard, IL
Blue • 2.5L I4 Engine
Blue • 2.5L I4 Engine
$41,980 • 47.6k miles
•••
#308 2015-2023 Toyota Highlander
CoPilot AI: It’s a “D-” Buy
- $700 Price Drop
- CARFAX: One Owner
- Motivation to Negotiate - Very High
More details
Price Drop
2020 Toyota Highlander Limited AWD • Summit, IL
Black • 3.5L V6 Engine
Black • 3.5L V6 Engine
$23,990 • 123.9k miles
•••
#173 2015-2023 Toyota Highlander
CoPilot AI: It’s a “C+” Buy
- $1,000 Price Drop
- Fair Price - $687 Below Market
- CARFAX: One Owner
More details
2021 Toyota Highlander Hybrid XLE FWD • Merrillville, IN
2.5L I4 Engine
2.5L I4 Engine
$36,998 • 39.4k miles
•••
#310 2015-2023 Toyota Highlander
CoPilot AI: It’s a “D-” Buy
- CARFAX: One Owner
- Motivation to Negotiate - Increasing
- Very Low Mileage
More details
Price Drop
2018 Toyota Highlander Limited AWD • Crystal Lake, IL
Green • 3.5L V6 Engine
Green • 3.5L V6 Engine
$19,999 • 151.2k miles
•••
#316 2015-2023 Toyota Highlander
CoPilot AI: It’s a “F” Buy
- $1,000 Price Drop
- Motivation to Negotiate - Very High
- Dealer Rating - 4.4 stars
More details
2023 Toyota Highlander XLE AWD • West Allis, WI
Black • 2.4L I4 Engine
Black • 2.4L I4 Engine
$38,995 • 27.3k miles
•••
#287 2015-2023 Toyota Highlander
CoPilot AI: It’s a “D+” Buy
- Very Low Mileage
- Dealer Rating - 4.7 stars
More details
Price Drop
2019 Toyota Highlander XLE AWD • Peru, IL
Silver • 3.5L V6 Engine
Silver • 3.5L V6 Engine
$22,456 • 109.4k miles
•••
#181 2015-2023 Toyota Highlander
CoPilot AI: It’s a “C+” Buy
- $840 Price Drop
- Fair Price - $460 Below Market
- Includes $145 Premium Upgrades
More details
Price Drop
2019 Toyota Highlander Hybrid Limited Platinum AWD • Tinley Park, IL
Silver • 3.5L V6 Engine
Silver • 3.5L V6 Engine
$35,999 • 45.2k miles
•••
#267 2015-2023 Toyota Highlander
CoPilot AI: It’s a “C-” Buy
- $1,000 Price Drop
- Includes $182 Premium Upgrades
- CARFAX: One Owner
More details
Price Drop
2022 Toyota Highlander XLE AWD • Elkhart, IN
Gray • 3.5L V6 Engine
Gray • 3.5L V6 Engine
$30,000 • 78.4k miles
•••
#98 2015-2023 Toyota Highlander
CoPilot AI: It’s a “B-” Buy
- $822 Price Drop
- Good Price - $1,099 Below Market
- Motivation to Negotiate - Very High
More details
Price Drop
2017 Toyota Highlander Limited AWD • Glenview, IL
White • 3.5L V6 Engine
White • 3.5L V6 Engine
$21,995 • 99k miles
•••
#120 2015-2023 Toyota Highlander
CoPilot AI: It’s a “B-” Buy
- $1,000 Price Drop
- Fair Price - $622 Below Market
- Includes $128 Premium Upgrades
More details
2023 Toyota Highlander Hybrid LE AWD • Schaumburg, IL
Silver • 2.5L I4 Engine
Silver • 2.5L I4 Engine
$40,998 • 15.4k miles
•••
#333 2015-2023 Toyota Highlander
CoPilot AI: It’s a “F” Buy
- Very Low Mileage
- Dealer Rating - 4.3 stars
More details
2023 Toyota Highlander L FWD • Milwaukee, WI
White • 2.4L I4 Engine
White • 2.4L I4 Engine
$27,995 • 71.6k miles
•••
#224 2015-2023 Toyota Highlander
CoPilot AI: It’s a “C+” Buy
- Fair Price - $296 Above Market
- CARFAX: One Owner
- Motivation to Negotiate - Increasing
More details
Price Drop
2022 Toyota Highlander XLE FWD • West Allis, WI
Black • 3.5L V6 Engine
Black • 3.5L V6 Engine
$30,944 • 45.2k miles
•••
#157 2015-2023 Toyota Highlander
CoPilot AI: It’s a “B-” Buy
- $1,022 Price Drop
- Fair Price - $848 Above Market
- Motivation to Negotiate - Increasing
More details
2026 Toyota Highlander
Mid-size Crossover
Seats
8
Fuel Economy
21City MPG
28Hwy MPG
NHTSA Rating Summary
Dimensions
Toyota Highlander for Sale by CityResearch More ModelsView more SUVs