New Search
Save
Sort
Share
Used Toyota Highlander for Sale in Chicago, IL
Highlanders for Sale at Dealers
Filters
Price
Year
Mileage
Trim
1
2021 Toyota Highlander XLE AWD • Aurora, IL
Blue • 3.5L V6 Engine
Blue • 3.5L V6 Engine
$34,995 • 31.1k miles
•••
#1 2015-2023 Toyota Highlander
CoPilot AI: It’s an “A+” Buy
- Great Price - $3,008 Below Market
- Includes $832 Premium Upgrades
- CARFAX: Clean Title, Not a rental or commercial vehicle
More details
2
2022 Toyota Highlander XLE AWD • Tinley Park, IL
Gray • 3.5L V6 Engine
Gray • 3.5L V6 Engine
$39,999 • 17.8k miles
•••
#2 2015-2023 Toyota Highlander
CoPilot AI: It’s an “A+” Buy
- Great Price - $10,834 Below Market
- Includes $559 Premium Upgrades
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
More details
3
Price Drop
2023 Toyota Highlander Hybrid Platinum AWD • Arlington Heights, IL
White • 2.5L I4 Engine
White • 2.5L I4 Engine
$47,795 • 34.8k miles
•••
#3 2015-2023 Toyota Highlander
CoPilot AI: It’s an “A+” Buy
- $200 Price Drop
- Great Price - $3,836 Below Market
- Includes $1,086 Premium Upgrades
More details
4
Price Drop
2022 Toyota Highlander XLE AWD • Melrose Park, IL
Gray • 3.5L V6 Engine
Gray • 3.5L V6 Engine
$33,900 • 46.7k miles
•••
#4 2015-2023 Toyota Highlander
CoPilot AI: It’s an “A+” Buy
- $100 Price Drop
- Great Price - $3,267 Below Market
- Includes $1,391 Premium Upgrades
More details
5
Price Drop
2021 Toyota Highlander XLE AWD • Northbrook, IL
Gray • 3.5L V6 Engine
Gray • 3.5L V6 Engine
$30,990 • 52.7k miles
•••
#5 2015-2023 Toyota Highlander
CoPilot AI: It’s an “A+” Buy
- $500 Price Drop
- Great Price - $2,900 Below Market
- Includes $781 Premium Upgrades
More details
6
Price Drop
2021 Toyota Highlander XLE AWD • Elgin, IL
Gray • 3.5L V6 Engine
Gray • 3.5L V6 Engine
$30,640 • 49.2k miles
•••
#6 2015-2023 Toyota Highlander
CoPilot AI: It’s an “A+” Buy
- $360 Price Drop
- Great Price - $2,316 Below Market
- CARFAX: Clean Title, Not a rental or commercial vehicle
More details
7
2023 Toyota Highlander L FWD • Chicago, IL
Silver • 2.4L I4 Engine
Silver • 2.4L I4 Engine
$33,990 • 21.2k miles
•••
#7 2015-2023 Toyota Highlander
CoPilot AI: It’s an “A+” Buy
- Great Price - $2,303 Below Market
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
- Very Low Mileage
More details
8
Price Drop
2022 Toyota Highlander L FWD • Milwaukee, WI
White • 3.5L V6 Engine
White • 3.5L V6 Engine
$29,900 • 35.5k miles
•••
#8 2015-2023 Toyota Highlander
CoPilot AI: It’s an “A+” Buy
- $600 Price Drop
- Great Price - $2,157 Below Market
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
More details
9
2018 Toyota Highlander XLE AWD • Elgin, IL
White • 3.5L V6 Engine
White • 3.5L V6 Engine
$26,500 • 51.4k miles
•••
#9 2015-2023 Toyota Highlander
CoPilot AI: It’s an “A+” Buy
- Great Price - $1,977 Below Market
- Includes $158 Premium Upgrades
- CARFAX: Clean Title, Not a rental or commercial vehicle
More details
10
Price Drop
2021 Toyota Highlander Hybrid Platinum AWD • Lincolnwood, IL
White • 2.5L I4 Engine
White • 2.5L I4 Engine
$40,353 • 56.3k miles
•••
#10 2015-2023 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- $1 Price Drop
- Great Price - $10,353 Below Market
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
More details
11
Price Drop
2023 Toyota Highlander L AWD • Fox Lake, IL
Blue • 2.4L I4 Engine
Blue • 2.4L I4 Engine
$33,465 • 31.4k miles
•••
#11 2015-2023 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- $1,420 Price Drop
- Great Price - $3,704 Below Market
- CARFAX: One Owner, Clean Title
More details
12
Price Drop
2020 Toyota Highlander LE AWD • Joliet, IL
Black • 3.5L V6 Engine
Black • 3.5L V6 Engine
$21,800 • 97.9k miles
•••
#12 2015-2023 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- $149 Price Drop
- Great Price - $3,597 Below Market
- CARFAX: Clean Title
More details
13
Price Drop
2023 Toyota Highlander LE AWD • Arlington Heights, IL
Silver • 2.4L I4 Engine
Silver • 2.4L I4 Engine
$30,295 • 39.5k miles
•••
#13 2015-2023 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- $200 Price Drop
- Great Price - $2,296 Below Market
- CARFAX: One Owner, Clean Title
More details
14
2020 Toyota Highlander XLE AWD • Sturtevant, WI
Silver • 3.5L V6 Engine
Silver • 3.5L V6 Engine
$27,500 • 67.8k miles
•••
#14 2015-2023 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- Great Price - $1,923 Below Market
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
- Average Mileage
More details
15
Price Drop
2022 Toyota Highlander LE AWD • Streamwood, IL
Silver • 3.5L V6 Engine
Silver • 3.5L V6 Engine
$28,490 • 56k miles
•••
#15 2015-2023 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- $300 Price Drop
- Great Price - $1,891 Below Market
- CARFAX: One Owner, Clean Title
More details
16
Price Drop
2016 Toyota Highlander XLE AWD • Milwaukee, WI
Green • 3.5L V6 Engine
Green • 3.5L V6 Engine
$17,995 • 118.7k miles
•••
#16 2015-2023 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- $1,000 Price Drop
- Great Price - $1,410 Below Market
- CARFAX: Clean Title, Not a rental or commercial vehicle
More details
17
2022 Toyota Highlander Limited AWD • West Allis, WI
Red • 3.5L V6 Engine
Red • 3.5L V6 Engine
$39,995 • 28.3k miles
•••
#17 2015-2023 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- Good Price - $1,366 Below Market
- Includes $840 Premium Upgrades
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
More details
18
Price Drop
2021 Toyota Highlander XLE AWD • Merrillville, IN
Silver • 3.5L V6 Engine
Silver • 3.5L V6 Engine
$33,184 • 41k miles • Certified
•••
#18 2015-2023 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- $371 Price Drop
- Good Price - $1,196 Below Market
- Includes $810 Premium Upgrades
More details
19
Price Drop
2022 Toyota Highlander XLE AWD • Calumet City, IL
Red • 3.5L V6 Engine
Red • 3.5L V6 Engine
$35,873 • 36.7k miles • Certified
•••
#19 2015-2023 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- $100 Price Drop
- Good Price - $1,112 Below Market
- Includes $832 Premium Upgrades
More details
20
Price Drop
2022 Toyota Highlander XLE FWD • Burbank, IL
Black • 3.5L V6 Engine
Black • 3.5L V6 Engine
$32,795 • 36.4k miles
•••
#20 2015-2023 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- $2,200 Price Drop
- Good Price - $1,026 Below Market
- Includes $832 Premium Upgrades
More details
21
Price Drop
2023 Toyota Highlander XSE AWD • Milwaukee, WI
Gray • 2.4L I4 Engine
Gray • 2.4L I4 Engine
$38,995 • 32.5k miles
•••
#21 2015-2023 Toyota Highlander
CoPilot AI: It’s an “A-” Buy
- $206 Price Drop
- Good Price - $2,095 Below Market
- Includes $1,100 Premium Upgrades
More details
22
Price Drop
2022 Toyota Highlander XLE AWD • Milwaukee, WI
Gray • 3.5L V6 Engine
Gray • 3.5L V6 Engine
$38,798 • 10.9k miles
•••
#22 2015-2023 Toyota Highlander
CoPilot AI: It’s an “A-” Buy
- $166 Price Drop
- Good Price - $2,083 Below Market
- Includes $559 Premium Upgrades
More details
23
Price Drop
2022 Toyota Highlander XSE AWD • Milwaukee, WI
Blue • 3.5L V6 Engine
Blue • 3.5L V6 Engine
$36,980 • 40.1k miles
•••
#23 2015-2023 Toyota Highlander
CoPilot AI: It’s an “A-” Buy
- $570 Price Drop
- Good Price - $1,976 Below Market
- Includes $1,903 Premium Upgrades
More details
24
Price Drop
2023 Toyota Highlander XLE AWD • West Allis, WI
Black • 2.4L I4 Engine
Black • 2.4L I4 Engine
$37,990 • 23.2k miles
•••
#24 2015-2023 Toyota Highlander
CoPilot AI: It’s an “A-” Buy
- $1,001 Price Drop
- Good Price - $1,838 Below Market
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
More details
25
2022 Toyota Highlander Platinum AWD • Oak Lawn, IL
Red • 3.5L V6 Engine
Red • 3.5L V6 Engine
$41,995 • 24.6k miles
•••
#25 2015-2023 Toyota Highlander
CoPilot AI: It’s an “A-” Buy
- Good Price - $1,469 Below Market
- Includes $479 Premium Upgrades
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
More details
2025 Toyota Highlander
Mid-size Crossover
Seats
8
Fuel Economy
35City MPG
35Hwy MPG
NHTSA Rating Summary
Dimensions
Toyota Highlander for Sale by CityResearch More ModelsView more SUVs