Used 2022 Toyota Highlander for Sale in Chicago, IL
Highlanders for Sale at Dealers, Ranked by CoPilot AI ?

#1 2021-2023 Toyota Highlander
CoPilot AI: It’s an “A+” Buy
- $393 Price Drop
- Great Price - $4,130 Below Market
- Includes $1,344 Premium Upgrades

#2 2021-2023 Toyota Highlander
CoPilot AI: It’s an “A+” Buy
- $704 Price Drop
- Great Price - $3,564 Below Market
- Includes $1,344 Premium Upgrades

#3 2021-2023 Toyota Highlander
CoPilot AI: It’s an “A+” Buy
- Great Price - $3,488 Below Market
- Includes $1,086 Premium Upgrades
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle

#4 2021-2023 Toyota Highlander
CoPilot AI: It’s an “A+” Buy
- $500 Price Drop
- Great Price - $3,011 Below Market
- Includes $832 Premium Upgrades
#5 2021-2023 Toyota Highlander
CoPilot AI: It’s an “A+” Buy
- $1,089 Price Drop
- Great Price - $3,297 Below Market
- Includes $559 Premium Upgrades
#6 2021-2023 Toyota Highlander
CoPilot AI: It’s an “A+” Buy
- $450 Price Drop
- Great Price - $2,894 Below Market
- Includes $832 Premium Upgrades
#7 2021-2023 Toyota Highlander
CoPilot AI: It’s an “A+” Buy
- $500 Price Drop
- Great Price - $2,818 Below Market
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
#8 2021-2023 Toyota Highlander
CoPilot AI: It’s an “A+” Buy
- $210 Price Drop
- Great Price - $2,693 Below Market
- Includes $832 Premium Upgrades
#9 2021-2023 Toyota Highlander
CoPilot AI: It’s an “A+” Buy
- $100 Price Drop
- Great Price - $2,654 Below Market
- Includes $1,391 Premium Upgrades
#10 2021-2023 Toyota Highlander
CoPilot AI: It’s an “A+” Buy
- Great Price - $2,634 Below Market
- Includes $1,391 Premium Upgrades
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
#11 2021-2023 Toyota Highlander
CoPilot AI: It’s an “A+” Buy
- $500 Price Drop
- Great Price - $2,557 Below Market
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
#12 2021-2023 Toyota Highlander
CoPilot AI: It’s an “A+” Buy
- $583 Price Drop
- Great Price - $2,285 Below Market
- Includes $1,391 Premium Upgrades
#13 2021-2023 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- $1,470 Price Drop
- Great Price - $9,432 Below Market
- Includes $479 Premium Upgrades
#14 2021-2023 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- $100 Price Drop
- Great Price - $4,586 Below Market
- Includes $559 Premium Upgrades
#15 2021-2023 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- Great Price - $3,766 Below Market
- CARFAX: Clean Title
- Very Low Mileage
#16 2021-2023 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- Great Price - $3,044 Below Market
- CARFAX: Clean Title
- Motivation to Negotiate - Increasing
#17 2021-2023 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- $305 Price Drop
- Great Price - $2,928 Below Market
- Includes $559 Premium Upgrades
#18 2021-2023 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- $1,982 Price Drop
- Great Price - $2,679 Below Market
- CARFAX: Clean Title, Not a rental or commercial vehicle
#19 2021-2023 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- $1,218 Price Drop
- Good Price - $1,546 Below Market
- Includes $840 Premium Upgrades
#20 2021-2023 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- Good Price - $1,207 Below Market
- Includes $1,391 Premium Upgrades
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
#21 2021-2023 Toyota Highlander
CoPilot AI: It’s an “A-” Buy
- Great Price - $3,703 Below Market
- Includes $479 Premium Upgrades
- CARFAX: Clean Title
#22 2021-2023 Toyota Highlander
CoPilot AI: It’s an “A-” Buy
- Good Price - $2,240 Below Market
- Includes $479 Premium Upgrades
- CARFAX: One Owner, Clean Title
#23 2021-2023 Toyota Highlander
CoPilot AI: It’s an “A-” Buy
- $421 Price Drop
- Good Price - $2,169 Below Market
- Includes $559 Premium Upgrades
#24 2021-2023 Toyota Highlander
CoPilot AI: It’s an “A-” Buy
- Good Price - $2,106 Below Market
- Includes $1,903 Premium Upgrades
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
#25 2021-2023 Toyota Highlander
CoPilot AI: It’s an “A-” Buy
- $780 Price Drop
- Good Price - $1,964 Below Market
- Includes $814 Premium Upgrades
2022 Toyota Highlander
The Basics
Performance
Safety
CoPilot Star Rating
The Good Stuff
Available Trims [1]
Hybrid XLE
- 3rd Row Seat
- Heated Front Seats
- Multi-Zone A/C
- Rear A/C
- 2nd Row Captain's Chairs/Rear Bucket Seats
- Sun Roof
- Heated Mirrors
- Premium Wheels
- Blind Spot Monitor
- Lane Departure Warning
- Security System
- Cross-Traffic Alert
- Lane Keeping Assist
- Adaptive Cruise Control
- Auxiliary Audio Input
- Back-Up Camera
- Bluetooth Connection
- WiFi Hotspot
- Steering Wheel Audio Controls
- Remote Engine Start
- Smartphone Integration
- Android Auto
- Apple CarPlay
- Navigation System
Vehicle Dimensions
Headroom/Legroom
Front Seats
- Headroom: 39.6
- 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
Why Use CoPilot?
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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.