New Search
Save
Sort
Used Toyota Highlander for Sale in Chicago, IL
Highlanders for Sale at Dealers, Ranked by CoPilot AI ?
Filters
Price
Year
Mileage
Trim
1
Price Drop
2021 Toyota Highlander XSE FWD • Milwaukee, WI
$37,642 • 20.3k miles
•••
#1 2015-2023 Toyota Highlander
CoPilot AI: It’s an “A+” Buy
- $393 Price Drop
- Great Price - $4,376 Below Market
- Includes $1,344 Premium Upgrades
See more about this car
2
2023 Toyota Highlander Limited AWD • Highland Park, IL
$43,980 • 5.4k miles
•••
#2 2015-2023 Toyota Highlander
CoPilot AI: It’s an “A+” Buy
- Great Price - $3,702 Below Market
- Includes $1,086 Premium Upgrades
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
3
Price Drop
2021 Toyota Highlander XSE AWD • Milwaukee, WI
$37,273 • 23.4k miles
•••
#3 2015-2023 Toyota Highlander
CoPilot AI: It’s an “A+” Buy
- $704 Price Drop
- Great Price - $3,425 Below Market
- Includes $1,344 Premium Upgrades
See more about this car
4
Price Drop
2021 Toyota Highlander XSE AWD • Matteson, IL
$36,995 • 28.8k miles • Certified
•••
#4 2015-2023 Toyota Highlander
CoPilot AI: It’s an “A+” Buy
- $1,771 Price Drop
- Great Price - $3,011 Below Market
- Includes $1,344 Premium Upgrades
See more about this car
5
Price Drop
2021 Toyota Highlander XLE AWD • Schererville, IN
$35,500 • 25.2k miles
•••
#5 2015-2023 Toyota Highlander
CoPilot AI: It’s an “A+” Buy
- $500 Price Drop
- Great Price - $2,830 Below Market
- Includes $832 Premium Upgrades
See more about this car
6
Price Drop
2021 Toyota Highlander Hybrid XLE FWD • Oak Lawn, IL
$36,635 • 17.4k miles
•••
#6 2015-2023 Toyota Highlander
CoPilot AI: It’s an “A+” Buy
- $365 Price Drop
- Great Price - $3,206 Below Market
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
7
2021 Toyota Highlander XLE AWD • Tinley Park, IL
$34,999 • 36.4k miles
•••
#7 2015-2023 Toyota Highlander
CoPilot AI: It’s an “A+” Buy
- Great Price - $2,844 Below Market
- Includes $1,391 Premium Upgrades
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
8
Price Drop
2022 Toyota Highlander XLE AWD • Chicago, IL
$40,390 • 17k miles
•••
#8 2015-2023 Toyota Highlander
CoPilot AI: It’s an “A+” Buy
- $400 Price Drop
- Great Price - $2,725 Below Market
- Includes $1,391 Premium Upgrades
See more about this car
9
Price Drop
2021 Toyota Highlander XLE AWD • Waukesha, WI
$33,790 • 39.2k miles
•••
#9 2015-2023 Toyota Highlander
CoPilot AI: It’s an “A+” Buy
- $1,125 Price Drop
- Great Price - $2,706 Below Market
- Includes $832 Premium Upgrades
See more about this car
10
2021 Toyota Highlander XLE AWD • Elmhurst, IL
$34,444 • 37.4k miles
•••
#10 2015-2023 Toyota Highlander
CoPilot AI: It’s an “A+” Buy
- Great Price - $2,649 Below Market
- Includes $832 Premium Upgrades
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
11
Price Drop
2020 Toyota Highlander XLE AWD • Streamwood, IL
$34,490 • 28.7k miles
•••
#11 2015-2023 Toyota Highlander
CoPilot AI: It’s an “A+” Buy
- $500 Price Drop
- Great Price - $2,565 Below Market
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
12
Price Drop
2021 Toyota Highlander XLE AWD • Northbrook, IL
$34,990 • 25.5k miles
•••
#12 2015-2023 Toyota Highlander
CoPilot AI: It’s an “A+” Buy
- $616 Price Drop
- Great Price - $2,534 Below Market
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
13
Price Drop
2021 Toyota Highlander XLE AWD • West Allis, WI
$34,412 • 38k miles
•••
#13 2015-2023 Toyota Highlander
CoPilot AI: It’s an “A+” Buy
- $583 Price Drop
- Great Price - $2,511 Below Market
- Includes $1,391 Premium Upgrades
See more about this car
14
Price Drop
2016 Toyota Highlander XLE AWD • Gurnee, IL
$23,100 • 89.1k miles
•••
#14 2015-2023 Toyota Highlander
CoPilot AI: It’s an “A+” Buy
- $700 Price Drop
- Great Price - $2,196 Below Market
- Includes $1,284 Premium Upgrades
See more about this car
15
Price Drop
2021 Toyota Highlander XLE AWD • South Bend, IN
$32,494 • 56.1k miles
•••
#15 2015-2023 Toyota Highlander
CoPilot AI: It’s an “A+” Buy
- $780 Price Drop
- Great Price - $2,140 Below Market
- Includes $818 Premium Upgrades
See more about this car
16
Price Drop
2023 Toyota Highlander L AWD • Westmont, IL
$41,487 • 12.6k miles
•••
#16 2015-2023 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- $1,470 Price Drop
- Great Price - $10,441 Below Market
- Includes $479 Premium Upgrades
See more about this car
17
Price Drop
2021 Toyota Highlander XLE AWD • Calumet City, IL
$30,989 • 39.5k miles
•••
#17 2015-2023 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- $3,784 Price Drop
- Great Price - $5,368 Below Market
- Includes $559 Premium Upgrades
See more about this car
18
Price Drop
2022 Toyota Highlander Platinum AWD • Calumet City, IL
$39,573 • 36k miles
•••
#18 2015-2023 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- $100 Price Drop
- Great Price - $4,794 Below Market
- Includes $559 Premium Upgrades
See more about this car
19
Price Drop
2021 Toyota Highlander Platinum AWD • Elkhorn, WI
$39,376 • 33k miles
•••
#19 2015-2023 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- $424 Price Drop
- Great Price - $3,709 Below Market
- Includes $559 Premium Upgrades
See more about this car
20
Price Drop
2021 Toyota Highlander XSE AWD • Mt Pleasant, WI
$34,990 • 49.7k miles • Certified
•••
#20 2015-2023 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- Great Price - $3,218 Below Market
- Includes $1,344 Premium Upgrades
- CARFAX: Clean Title, Not a rental or commercial vehicle
See more about this car
21
Price Drop
2022 Toyota Highlander XLE AWD • Libertyville, IL
$37,690 • 31.7k miles
•••
#21 2015-2023 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- $305 Price Drop
- Great Price - $3,096 Below Market
- Includes $559 Premium Upgrades
See more about this car
22
Price Drop
2021 Toyota Highlander Platinum AWD • Northbrook, IL
$39,990 • 28.8k miles
•••
#22 2015-2023 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- $1,982 Price Drop
- Great Price - $2,806 Below Market
- CARFAX: Clean Title, Not a rental or commercial vehicle
See more about this car
23
Price Drop
2020 Toyota Highlander XLE FWD • Sycamore, IL
$28,490 • 77.3k miles
•••
#23 2015-2023 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- Great Price - $2,298 Below Market
- Includes $905 Premium Upgrades
- CARFAX: Clean Title
See more about this car
24
Price Drop
2021 Toyota Highlander XLE AWD • Westmont, IL
$34,216 • 35.3k miles
•••
#24 2015-2023 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- $1,205 Price Drop
- Great Price - $2,211 Below Market
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
25
2021 Toyota Highlander XLE AWD • Elkhart, IN
$36,995 • 28.3k miles
•••
#25 2015-2023 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- Good Price - $1,427 Below Market
- Includes $1,391 Premium Upgrades
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
1-25 of 473 results
2023 Toyota Highlander
Mid-size Crossover
The Basics
8 Seats
16 Suitcases in Trunk
SPACIOUS
84 With Rear Seats Folded
Performance
Fuel Economy
none
undefined - undefinedCity MPG
undefined - undefinedHwy MPG
Quickness
SLUGGISH
Safety
NHTSA® Safety
CoPilot Star Rating
Copilot Rating
The Good Stuff
Available Trims [1]
L
- 3rd Row Seat
- Multi-Zone A/C
- Rear A/C
- Heated Mirrors
- Premium Wheels
- Lane Departure Warning
- Lane Keeping Assist
- Adaptive Cruise Control
- Auxiliary Audio Input
- Back-Up Camera
- Bluetooth Connection
- WiFi Hotspot
- Steering Wheel Audio Controls
- Smartphone Integration
- Android Auto
- Apple CarPlay
Vehicle Dimensions
Headroom/Legroom
Front Seats
- Headroom: 41.2
- Legroom: 42
Back Seats [1st row]
- Headroom: 39.4
- Legroom: 41
Back Seats [2nd row]
- Headroom: 36.1
- Legroom: 27.7
Available Drive Trains
Available Engines
Available Transmissions
Available Colors
MakesUsed Toyota Models for SaleUsed Makes and ModelsToyota Highlander for Sale by CityUsed Cars for Sale by CityMore Cars
Why Use CoPilot?
Shop and buy your next car with confidence. CoPilot searches every car at every dealer, every day, and ranks them based on what matters to you.
When you shop for a new or used car, CoPilot helps you know more. We search every car at every dealer so you don't have to, we give you data and insights you won't find anywhere else, and we rank every car so it's easy to find the best car at the best price.
When you're ready to buy your next car, CoPilot helps you make sure you never get taken advantage of at the dealership. Would you like to know more than the salesperson? CoPilot helps you avoid any tricks, traps, and scams. Know how and what you can negotiate. With CoPilot, you'll save time, money, and frustration.