Used Toyota Highlander in Chicago, IL For Sale Under $40,000 (93 results)

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Chicago, IL

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2024 Toyota Highlander

Discover the 2024 Toyota Highlander featuring an automatic transmission and all-wheel drive, perfect for tackling city streets and suburban adventures with ease

automatic

gasoline

Chicago, IL

$39,977

2021 toyota highlander limited

This 2021 Toyota Highlander Limited features a clean vehicle history with no accidents. Fully loaded with leather seating, Bluetooth, and a rearview camera, it's perfect for family trips with plenty of space and modern tech

17,280 mi.

Black

Suv

automatic

gasoline

Chicago, IL

$39,890

2021 Toyota Highlander

Discover this 2021 Toyota Highlander with all-wheel drive, perfect for family adventures and city driving alike. With a sleek design and advanced features, it offers both comfort and style!

automatic

gasoline

Chicago, IL

$39,690

2023 Toyota Highlander

Explore this 2023 Toyota Highlander with all-wheel drive and automatic transmission, perfect for your family adventures. It blends comfort and style, ready for the road ahead!

automatic

gasoline

Chicago, IL

$39,577

2023 toyota highlander xle

This stunning 2023 Toyota Highlander XLE AWD features a spacious interior with 3rd row seating and an array of modern tech, including an 8'' multimedia display and rear parking camera. Buy with confidence with a 90-Day warranty and maintenance program!

30,682 mi.

White

automatic

gasoline

Chicago, IL

$39,577

2023 toyota highlander hybrid xle

This 2023 Toyota Highlander Hybrid XLE is a one-owner beauty in Wind Chill Pearl, featuring luxurious leather, USB ports, Bluetooth, and a rearview camera. Enjoy the efficiency of a hybrid with spacious third-row seating

51,145 mi.

Wind chill pearl

Suv

automatic

hybrid

Chicago, IL

$39,290

2023 Toyota Highlander

Experience the 2023 Toyota Highlander, featuring a sleek design and advanced technology, perfect for families and adventurers alike

automatic

hybrid

Chicago, IL

$39,090

2021 toyota highlander xle

Experience the 2021 Toyota Highlander XLE in stunning Ruby Flare Pearl. This one-owner SUV features heated seats, a sunroof, advanced safety tech, and a spacious interior, perfect for families and adventures alike

30,175 mi.

Red

automatic

gasoline

Chicago, IL

$39,000

2023 toyota highlander xle

Discover the elegant 2023 Toyota Highlander XLE, featuring 3rd-row split-bench seating, a powerful audio system, and convenient power liftgate. Stylish and practical, this SUV is perfect for families on the go!

26,502 mi.

Blueprint

Suv

automatic

gasoline

Chicago, IL

$37,916

2023 toyota highlander xle

Experience the luxurious ride of a 2023 Toyota Highlander XLE with features like a back-up camera, Bluetooth, Apple CarPlay, and a Power moonroof, ensuring comfort and convenience in every journey

35,115 mi.

Celestial silver metallic

4d sport utility

automatic

gasoline

Chicago, IL

$37,000

2021 toyota highlander platinum

Discover luxury in the 2021 Toyota Highlander Platinum, featuring a stunning Blizzard Pearl exterior, advanced safety features, and a spacious interior with leather and a panoramic roof. A perfect blend of comfort and functionality

51,402 mi.

White

automatic

gasoline

Chicago, IL

$36,998

2023 toyota highlander xle

Discover this luxurious 2023 Toyota Highlander XLE in Midnight Black Metallic, featuring a powerful 2.4L engine, a spacious 4D Sport Utility body, and convenient features like heated seats and a power moonroof

24,131 mi.

Black

Sport utility

automatic

gasoline

Chicago, IL

$36,993

2021 toyota highlander in chicago, illinois

This 2021 Toyota Highlander XSE, showcased in a stunning Ruby Flare Pearl exterior with a sleek black interior, combines style and practicality for any family

Red

automatic

Chicago, IL

$36,898

2021 toyota highlander hybrid xle

Experience the blend of efficiency and comfort with this 2021 Toyota Highlander Hybrid XLE, featuring a sleek Moon Dust exterior and a spacious interior with Graphite finishes

71,497 mi.

Moon dust

Chicago, IL

$36,590

2022 toyota highlander xle

This 2022 Toyota Highlander XLE in Blueprint color boasts an impressive list of features including Apple CarPlay, Android Auto, heated seats, and more. With only 31,679 miles, it’s a certified vehicle with an extensive warranty

31,679 mi.

Blueprint

automatic

gasoline

Chicago, IL

$35,999

2021 toyota highlander xle

This 2021 Toyota Highlander XLE is a striking red 4D Sport Utility with low mileage of just 16,669 miles. It features an efficient 3.5L V6 engine, providing a commendable 20/27 MPG, backed by an 8-speed automatic transmission

16,669 mi.

Red

Sport utility

automatic

gasoline

Chicago, IL

$35,700

2021 toyota highlander xse

This 2021 Toyota Highlander XSE AWD stands out with its Magnetic Gray Metallic finish, a powerful 3.5L V6 engine, and sporty handling, perfect for family adventures and daily drives alike

52,736 mi.

Notdoor

Suv

automatic

gasoline

Chicago, IL

$34,995

2021 toyota highlander xle

Explore the 2021 Toyota Highlander XLE in Ruby Flare Pearl, featuring all-wheel drive and a sleek graphite interior. Only 40,388 miles with automatic transmission, this SUV is ready for your next adventure!

40,388 mi.

Ruby flare pearl

automatic

gasoline

Chicago, IL

$34,995

2023 toyota highlander l

Experience the 2023 Toyota Highlander L in Celestial Silver Metallic, featuring 3rd row seating, 18'' alloy wheels, and advanced safety tech for your family's journeys

24,423 mi.

Silver

automatic

gasoline

Chicago, IL

$34,577

2021 Toyota Highlander

Experience the versatility of this 2021 Toyota Highlander, featuring an all-wheel drive system and smooth automatic transmission for an enjoyable ride in any condition

automatic

gasoline

Chicago, IL

$34,495