New Search
Save
Sort
Used 2020 Toyota Highlander for Sale in Chicago, IL
Highlanders for Sale at Dealers, Ranked by CoPilot AI ?
Filters
Price
Year
Mileage
Trim
1
Toyota Highlander XSE AWD • Lincolnwood, IL
$36,588 • 18.5k miles
•••
#1 2019-2021 Toyota Highlander
CoPilot AI: It’s an “A+” Buy
- Great Price - $2,742 Below Market
- Includes $1,344 Premium Upgrades
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
2
Toyota Highlander XLE AWD • Calumet City, IL
$36,473 • 8.5k miles
•••
#2 2019-2021 Toyota Highlander
CoPilot AI: It’s an “A+” Buy
- Great Price - $2,737 Below Market
- Includes $1,311 Premium Upgrades
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
3
Price Drop
Toyota Highlander XSE FWD • Elmhurst, IL
$33,406 • 24.7k miles
•••
#3 2019-2021 Toyota Highlander
CoPilot AI: It’s an “A+” Buy
- $1,043 Price Drop
- Great Price - $5,302 Below Market
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
4
Price Drop
Toyota Highlander XLE AWD • Northbrook, IL
$32,990 • 37.7k miles
•••
#4 2019-2021 Toyota Highlander
CoPilot AI: It’s an “A+” Buy
- $500 Price Drop
- Great Price - $2,593 Below Market
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
5
Price Drop
Toyota Highlander LE AWD • Oak Lawn, IL
$29,500 • 35.7k miles
•••
#5 2019-2021 Toyota Highlander
CoPilot AI: It’s an “A+” Buy
- $400 Price Drop
- Great Price - $2,080 Below Market
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
6
Price Drop
Toyota Highlander Hybrid Platinum AWD • Palatine, IL
$36,526 • 58k miles
•••
#6 2019-2021 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- Great Price - $4,553 Below Market
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
- Motivation to Negotiate - Increasing
See more about this car
7
Price Drop
Toyota Highlander Hybrid XLE AWD • Northbrook, IL
$28,490 • 77.8k miles
•••
#7 2019-2021 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- $498 Price Drop
- Great Price - $4,158 Below Market
- CARFAX: Clean Title, Not a rental or commercial vehicle
See more about this car
8
Price Drop
Toyota Highlander Hybrid LE AWD • Schererville, IN
$29,500 • 51.6k miles
•••
#8 2019-2021 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- $400 Price Drop
- Great Price - $2,970 Below Market
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
9
Toyota Highlander XLE AWD • Lincolnwood, IL
$35,502 • 23.1k miles
•••
#9 2019-2021 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- Good Price - $2,242 Below Market
- Includes $1,311 Premium Upgrades
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
10
Price Drop
Toyota Highlander XSE AWD • Milwaukee, WI
$36,800 • 23.8k miles
•••
#10 2019-2021 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- $200 Price Drop
- Good Price - $2,214 Below Market
- Includes $1,344 Premium Upgrades
See more about this car
11
Toyota Highlander XLE AWD • South Bend, IN
$33,332 • 49k miles
•••
#11 2019-2021 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- Great Price - $2,179 Below Market
- Includes $817 Premium Upgrades
- CARFAX: Clean Title
See more about this car
12
Price Drop
Toyota Highlander XLE AWD • Michigan City, IN
$24,955 • 92.1k miles
•••
#12 2019-2021 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- $1 Price Drop
- Great Price - $1,933 Below Market
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
13
Toyota Highlander XLE FWD • Glencoe, IL
$24,991 • 82.3k miles
•••
#13 2019-2021 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- Great Price - $1,929 Below Market
- Includes $501 Premium Upgrades
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
14
Price Drop
Toyota Highlander XLE AWD • Mt Pleasant, WI
$34,597 • 32.8k miles
•••
#14 2019-2021 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- $393 Price Drop
- Good Price - $1,857 Below Market
- Includes $832 Premium Upgrades
See more about this car
15
Toyota Highlander Hybrid Limited AWD • Palatine, IL
$37,550 • 26.6k miles
•••
#15 2019-2021 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- Good Price - $1,471 Below Market
- Includes $813 Premium Upgrades
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
16
Price Drop
Toyota Highlander Limited FWD • Milwaukee, WI
$36,995 • 19.8k miles
•••
#16 2019-2021 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- $62 Price Drop
- Good Price - $1,343 Below Market
- Includes $1,054 Premium Upgrades
See more about this car
17
Price Drop
Toyota Highlander XLE AWD • West Allis, WI
$34,490 • 38.1k miles
•••
#17 2019-2021 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- $501 Price Drop
- Good Price - $1,323 Below Market
- Includes $832 Premium Upgrades
See more about this car
18
Price Drop
Toyota Highlander XLE AWD • Milwaukee, WI
$33,775 • 45.6k miles
•••
#18 2019-2021 Toyota Highlander
CoPilot AI: It’s an “A-” Buy
- $200 Price Drop
- Good Price - $1,719 Below Market
- Includes $1,375 Premium Upgrades
See more about this car
19
Price Drop
Toyota Highlander XSE AWD • Palatine, IL
$34,996 • 46.9k miles
•••
#19 2019-2021 Toyota Highlander
CoPilot AI: It’s an “A-” Buy
- $803 Price Drop
- Good Price - $1,653 Below Market
- Includes $1,330 Premium Upgrades
See more about this car
20
Price Drop
Toyota Highlander XLE AWD • Chicago, IL
$30,715 • 47.1k miles
•••
#20 2019-2021 Toyota Highlander
CoPilot AI: It’s an “A-” Buy
- Good Price - $1,627 Below Market
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
- Motivation to Negotiate - Very High
See more about this car
21
Price Drop
Toyota Highlander LE AWD • Fox Lake, IL
$30,000 • 19.5k miles
•••
#21 2019-2021 Toyota Highlander
CoPilot AI: It’s an “A-” Buy
- $253 Price Drop
- Good Price - $1,583 Below Market
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
22
Price Drop
Toyota Highlander XLE AWD • Chicago, IL
$34,890 • 27.8k miles
•••
#22 2019-2021 Toyota Highlander
CoPilot AI: It’s an “A-” Buy
- $100 Price Drop
- Good Price - $1,569 Below Market
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
23
Toyota Highlander XLE AWD • Northbrook, IL
$34,490 • 27.1k miles
•••
#23 2019-2021 Toyota Highlander
CoPilot AI: It’s an “A-” Buy
- Good Price - $1,505 Below Market
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
- Motivation to Negotiate - Increasing
See more about this car
24
Price Drop
Toyota Highlander Hybrid XLE AWD • Merrillville, IN
$31,750 • 56.1k miles • Certified
•••
#24 2019-2021 Toyota Highlander
CoPilot AI: It’s an “A-” Buy
- $238 Price Drop
- Good Price - $1,302 Below Market
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
25
Price Drop
Toyota Highlander XLE AWD • Calumet City, IL
$35,273 • 23.3k miles
•••
#25 2019-2021 Toyota Highlander
CoPilot AI: It’s an “A-” Buy
- $100 Price Drop
- Good Price - $1,195 Below Market
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
2020 Toyota Highlander
Mid-size Crossover
Seats
7
Fuel Economy
36 - 36City MPG
35 - 35Hwy MPG
NHTSA Rating Summary
Copilot Rating
Dimensions
Most Popular Models like HighlanderToyota Highlander near Chicago, ILOther Years
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.