Used Toyota Highlander in Chicago, IL For Sale Under $50,000 (100 results)

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City

Chicago, IL

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2022 toyota highlander hybrid xle

Discover the stylish 2022 Toyota Highlander Hybrid XLE in Wind Chill Pearl, featuring low mileage and a refined interior, perfect for family adventures

18,539 mi.

Wind chill pearl

Chicago, IL

$45,890

2023 toyota highlander hybrid xle

Explore this 2023 Toyota Highlander Hybrid XLE, featuring a stunning Magnetic Gray Metallic exterior and a sleek black interior, ideal for families seeking efficiency and comfort

21,366 mi.

Silver

Chicago, IL

$44,990

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2022 toyota highlander in chicago, illinois

Explore the 2022 Toyota Highlander Platinum, featuring a striking Blueprint exterior and luxurious Glazed Caramel interior. A perfect balance of style and comfort awaits you!

Blue

automatic

Chicago, IL

$43,492

2024 toyota highlander xle

Discover the 2024 Toyota Highlander XLE in stunning Magnetic Gray Metallic. Enjoy the luxury of leather, heated seats, a panoramic moonroof, and cutting-edge tech features for a safe, comfortable drive

16,435 mi.

Magnetic gray metallic

automatic

gasoline

Chicago, IL

$43,158

2022 toyota highlander hybrid limited

Discover this stunning 2022 Toyota Highlander Hybrid Limited in Wind Chill Pearl with a clean history and only one owner. Enjoy luxurious features like leather seating and advanced safety technology

17,879 mi.

Wind chill pearl

Suv

automatic

hybrid

Chicago, IL

$42,490

2024 toyota highlander le

This stunning 2024 Toyota Highlander LE features all-wheel drive and a spacious interior with 3rd row seating. Enjoy the convenience of an 8-inch multimedia system, a power liftgate, and a rear parking camera. It's Toyota Certified with a 7-year warranty!

20,812 mi.

Celestial silver metallic

automatic

gasoline

Chicago, IL

$41,777

2024 toyota highlander le

This 2024 Toyota Highlander LE features all-wheel drive, a spacious interior with split-bench 3rd row seating, and modern conveniences like an 8" Toyota Audio Multimedia system and rear parking camera

23,010 mi.

Notdoor

automatic

gasoline

Chicago, IL

$40,977

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