Used Toyota Highlander for Sale near Chicago, IL

376 results

Chicago, IL

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2021 Toyota Highlander

XSE AWD

80,354 miles

$28,500

Good Deal

Kenosha, WI

49 mi away

Year:: 2021
Make:: Toyota
Model:: Highlander
Body type:: SUV / Crossover
Doors:: 4 doors
Drivetrain:: All-Wheel Drive
Engine:: 295 hp 3.5L V6
Exterior color:: Black (Charcoal)
Combined gas mileage:: 23 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 80,354
Stock number:: M25529A
VIN:: 5TDJZRBH7MS149011

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2023 Toyota Highlander

L AWD

28,027 miles

$33,490

Good Deal

Northbrook, IL

19 mi away

Year:: 2023
Make:: Toyota
Model:: Highlander
Body type:: SUV / Crossover
Doors:: 4 doors
Drivetrain:: All-Wheel Drive
Engine:: 265 hp 2.4L I4
Exterior color:: Black
Combined gas mileage:: 24 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: Automatic
Mileage:: 28,027
Stock number:: R2N514328
VIN:: 5TDKDRBH0PS514328

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2024 Toyota Highlander

LE AWD

49,055 miles

$32,736

Fair Deal

Calumet City, IL

19 mi away

Year:: 2024
Make:: Toyota
Model:: Highlander
Body type:: SUV / Crossover
Doors:: 4 doors
Drivetrain:: All-Wheel Drive
Engine:: 265 hp 2.4L I4
Exterior color:: Magnetic Gray Metallic
Combined gas mileage:: 24 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 49,055
Stock number:: P7203
VIN:: 5TDKDRBH4RS556343

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2017 Toyota Highlander

XLE AWD

77,442 miles

$21,995

Good Deal

Crete, IL

29 mi away

Year:: 2017
Make:: Toyota
Model:: Highlander
Body type:: SUV / Crossover
Doors:: 4 doors
Drivetrain:: All-Wheel Drive
Engine:: 295 hp 3.5L V6
Exterior color:: Black
Combined gas mileage:: 22 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 77,442
Stock number:: 448166
VIN:: 5TDJZRFH8HS448166

2021 Toyota Highlander

XSE AWD

70,497 miles

$29,200

Great Deal

Lake Villa, IL

43 mi away

Year:: 2021
Make:: Toyota
Model:: Highlander
Body type:: SUV / Crossover
Doors:: 4 doors
Drivetrain:: All-Wheel Drive
Engine:: 295 hp 3.5L V6
Exterior color:: Magnetic Gray Metallic
Combined gas mileage:: 23 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: Automatic
Mileage:: 70,497
Stock number:: LV565
VIN:: 5TDLZRBH2MS147269

2019 Toyota Highlander

XLE AWD

80,278 miles

$22,895

Good Deal

Des Plaines, IL

18 mi away

Year:: 2019
Make:: Toyota
Model:: Highlander
Body type:: SUV / Crossover
Doors:: 4 doors
Drivetrain:: All-Wheel Drive
Exterior color:: Black
Interior color:: Black
Mileage:: 80,278
Stock number:: JU17978A
VIN:: 5TDJZRFH5KS739585

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2023 Toyota Highlander

L AWD

49,461 miles

$31,421

Good Deal

Certified Pre-Owned

Waukegan, IL

36 mi away

Year:: 2023
Make:: Toyota
Model:: Highlander
Body type:: SUV / Crossover
Doors:: 4 doors
Drivetrain:: All-Wheel Drive
Engine:: 265 hp 2.4L I4
Exterior color:: Silver
Combined gas mileage:: 24 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: Automatic
Mileage:: 49,461
Stock number:: T28830A
VIN:: 5TDKDRBH5PS041963

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2016 Toyota Highlander

111,350 miles

$14,999

Good Deal

Oak Lawn, IL

12 mi away

Year:: 2016
Make:: Toyota
Model:: Highlander
Body type:: SUV / Crossover
Doors:: 4 doors
Drivetrain:: Front-Wheel Drive
Engine:: 270 hp 3.5L V6
Exterior color:: Nautical Blue Metallic
Fuel type:: Gasoline
Interior color:: Almond
Transmission:: 6-Speed Automatic Overdrive
Mileage:: 111,350
Stock number:: 38670A
VIN:: 5TDZARFH8GS017416

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2014 Toyota Highlander

XLE AWD

185,487 miles

$11,895

Fair Deal

Northbrook, IL

19 mi away

Year:: 2014
Make:: Toyota
Model:: Highlander
Body type:: SUV / Crossover
Doors:: 4 doors
Drivetrain:: All-Wheel Drive
Engine:: 270 hp 3.5L V6
Exterior color:: Green
Combined gas mileage:: 21 MPG
Fuel type:: Gasoline
Interior color:: Gray
Transmission:: Automatic
Mileage:: 185,487
Stock number:: 038047
VIN:: 5TDJKRFHXES038047

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2014 Toyota Highlander

132,528 miles

$12,999

Good Deal

Gurnee, IL

39 mi away

Year:: 2014
Make:: Toyota
Model:: Highlander
Body type:: SUV / Crossover
Doors:: 4 doors
Drivetrain:: Front-Wheel Drive
Engine:: 270 hp 3.5L V6
Exterior color:: White (Blizzard Pearl)
Fuel type:: Gasoline
Interior color:: Almond
Transmission:: 6-Speed Automatic Overdrive
Mileage:: 132,528
Stock number:: GV29816A
VIN:: 5TDZKRFH9ES030833

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2021 Toyota Highlander

Limited AWD

77,332 miles

$28,694

Great Deal

Frankfort, IL

30 mi away

Year:: 2021
Make:: Toyota
Model:: Highlander
Body type:: SUV / Crossover
Doors:: 4 doors
Drivetrain:: All-Wheel Drive
Engine:: 295 hp 3.5L V6
Exterior color:: Blueprint
Combined gas mileage:: 23 MPG
Fuel type:: Gasoline
Interior color:: Gray (Graphite)
Transmission:: 8-Speed Automatic
Mileage:: 77,332
Stock number:: 60364S
VIN:: 5TDDZRBH2MS120786

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2019 Toyota Highlander

SE AWD

122,588 miles

$20,700

Good Deal

Oak Forest, IL

21 mi away

Year:: 2019
Make:: Toyota
Model:: Highlander
Body type:: SUV / Crossover
Doors:: 4 doors
Drivetrain:: All-Wheel Drive
Engine:: 295 hp 3.5L V6
Exterior color:: Midnight Black Metallic
Combined gas mileage:: 22 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 122,588
Stock number:: 45495
VIN:: 5TDJZRFH2KS991004

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2023 Toyota Highlander

XLE FWD

73,150 miles

$29,395

Great Deal

Certified Pre-Owned

Matteson, IL

27 mi away

Year:: 2023
Make:: Toyota
Model:: Highlander
Body type:: SUV / Crossover
Doors:: 4 doors
Drivetrain:: Front-Wheel Drive
Engine:: 265 hp 2.4L I4
Exterior color:: Celestial Silver Metallic
Combined gas mileage:: 25 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: Automatic
Mileage:: 73,150
Stock number:: P524681
VIN:: 5TDKDRAH9PS524681

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2022 Toyota Highlander

XLE AWD

26,427 miles

$34,283

Good Deal

Lake Bluff, IL

30 mi away

Year:: 2022
Make:: Toyota
Model:: Highlander
Body type:: SUV / Crossover
Doors:: 4 doors
Drivetrain:: All-Wheel Drive
Engine:: 295 hp 3.5L V6
Exterior color:: Midnight Black Metallic
Combined gas mileage:: 23 MPG
Fuel type:: Gasoline
Interior color:: Glazed Caramel
Transmission:: 8-Speed Automatic
Mileage:: 26,427
Stock number:: 53P108
VIN:: 5TDHZRBH4NS577604

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2021 Toyota Highlander

XSE AWD

80,354 miles

$28,500

Good Deal

Kenosha, WI

49 mi away

Year:: 2021
Make:: Toyota
Model:: Highlander
Body type:: SUV / Crossover
Doors:: 4 doors
Drivetrain:: All-Wheel Drive
Engine:: 295 hp 3.5L V6
Exterior color:: Black (Charcoal)
Combined gas mileage:: 23 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 80,354
Stock number:: M25529A
VIN:: 5TDJZRBH7MS149011

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2024 Toyota Highlander

XLE AWD

43,425 miles

$34,800

Great Deal

Barrington, IL

31 mi away

Year:: 2024
Make:: Toyota
Model:: Highlander
Body type:: SUV / Crossover
Doors:: 4 doors
Drivetrain:: All-Wheel Drive
Engine:: 265 hp 2.4L I4
Exterior color:: Celestial Silver Metallic
Combined gas mileage:: 24 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 43,425
Stock number:: PHR3106
VIN:: 5TDKDRBH5RS536151

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2016 Toyota Highlander

Limited Platinum AWD

88,493 miles

$20,691

Good Deal

Westmont, IL

18 mi away

Year:: 2016
Make:: Toyota
Model:: Highlander
Body type:: SUV / Crossover
Doors:: 4 doors
Drivetrain:: All-Wheel Drive
Engine:: 270 hp 3.5L V6
Exterior color:: White (Blizzard Pearl)
Combined gas mileage:: 21 MPG
Fuel type:: Gasoline
Interior color:: Almond
Transmission:: Automatic
Mileage:: 88,493
Stock number:: GS350387
VIN:: 5TDDKRFH5GS350387

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2015 Toyota Highlander

XLE

112,309 miles

$16,690

Good Deal

Chicago, IL

2 mi away

Year:: 2015
Make:: Toyota
Model:: Highlander
Body type:: SUV / Crossover
Doors:: 4 doors
Drivetrain:: Front-Wheel Drive
Engine:: 270 hp 3.5L V6
Exterior color:: Attitude Black Metallic
Combined gas mileage:: 22 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 6-Speed Automatic
Mileage:: 112,309
Stock number:: T259A
VIN:: 5TDJKRFHXFS086617

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2019 Toyota Highlander

XLE AWD

76,016 miles

$24,357

Good Deal

Elmhurst, IL

17 mi away

Year:: 2019
Make:: Toyota
Model:: Highlander
Body type:: SUV / Crossover
Doors:: 4 doors
Drivetrain:: All-Wheel Drive
Engine:: 295 hp 3.5L V6
Exterior color:: Predawn Gray Mica
Combined gas mileage:: 22 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 76,016
Stock number:: P6010
VIN:: 5TDJZRFH6KS984668

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2017 Toyota Highlander

SE AWD

98,900 miles

$21,500

Fair Deal

Kenosha, WI

49 mi away

Year:: 2017
Make:: Toyota
Model:: Highlander
Body type:: SUV / Crossover
Doors:: 4 doors
Drivetrain:: All-Wheel Drive
Engine:: 295 hp 3.5L V6
Exterior color:: Red
Combined gas mileage:: 22 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 98,900
Stock number:: 6586
VIN:: 5TDJZRFH5HS470724

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2016 Toyota Highlander

Limited Platinum AWD

118,404 miles

$19,550

Good Deal

Certified Pre-Owned

Joliet, IL

36 mi away

Year:: 2016
Make:: Toyota
Model:: Highlander
Body type:: SUV / Crossover
Doors:: 4 doors
Drivetrain:: All-Wheel Drive
Engine:: 270 hp 3.5L V6
Exterior color:: White (Blizzard Pearl)
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 6-Speed Automatic Overdrive
Mileage:: 118,404
Stock number:: B6486A
VIN:: 5TDDKRFH6GS257913

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2011 Toyota Highlander

Base

132,500 miles

$10,799

Fair Deal

Elgin, IL

34 mi away

Year:: 2011
Make:: Toyota
Model:: Highlander
Body type:: SUV / Crossover
Doors:: 4 doors
Drivetrain:: Front-Wheel Drive
Engine:: 187 hp 2.7L I4
Exterior color:: Gray
Fuel type:: Gasoline
Interior color:: Gray
Transmission:: 5-Speed Automatic
Mileage:: 132,500
Stock number:: 070624
VIN:: 5TDBK3EH8BS070624

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2017 Toyota Highlander

Limited Platinum AWD

143,038 miles

$17,987

Good Deal

Bartlett, IL

32 mi away

Year:: 2017
Make:: Toyota
Model:: Highlander
Body type:: SUV / Crossover
Doors:: 4 doors
Drivetrain:: All-Wheel Drive
Engine:: 295 hp 3.5L V6
Exterior color:: Black
Combined gas mileage:: 22 MPG
Fuel type:: Gasoline
Transmission:: Automatic
Mileage:: 143,038
Stock number:: DH23569A
VIN:: 5TDDZRFH4HS453877

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Overview

Reviews

FAQs

CarGurus recommends the 2022 Toyota Highlander

## Summary - With 4,569 currently listed for sale on CarGurus and an **average price of $32,534.00**, 33.8% of 2022 Toyota Highlanders for sale on CarGurus are rated as good or great deals. - **Favorably reviewed:** Owners rated the 2022 Toyota Highlander 4.58 / 5 stars. - **82.2% of 2022 Highlander models on CarGurus are accident free**. - The 2022 Toyota Highlander features a spacious and comfortable interior, excellent safety ratings, and is valued for its fuel efficiency, especially in hybrid models. ## Why it stands out The 2022 Toyota Highlander is designed with family-friendly features and a focus on reliability. This model stands out in the midsize SUV market due to its generous cargo space, upscale interior, and comprehensive safety technology. Owners appreciate its smooth ride quality combined with an array of safety features, including Toyota Safety Sense, which enhances driver confidence. The Highlander's balance of performance, comfort, and efficiency makes it a strong contender for buyers in search of a dependable family vehicle. ## Other model years to consider - **[2021 Toyota Highlander](https://www.cargurus.com/Cars/l-Used-2021-Toyota-Highlander-c30910)** - Average price: $29,279.00 - Good/great deal percentage: 34.6% - User rating: 4.82 / 5 - Total listings: 3,126 - **[2019 Toyota Highlander](https://www.cargurus.com/Cars/l-Used-2019-Toyota-Highlander-c27941)** - Average price: $23,139.00 - Good/great deal percentage: 37.3% - User rating: 4.57 / 5 - Total listings: 2,654 - **[2018 Toyota Highlander](https://www.cargurus.com/Cars/l-Used-2018-Toyota-Highlander-c26930)** - Average price: $21,263.00 - Good/great deal percentage: 38.0% - User rating: 4.23 / 5 - Total listings: 2,785 These recommendations are based on CarGurus' proprietary market data from February 20, 2026, CarGurus experts' opinions, and generative AI.

4.6 Overall rating

(691 reviews)

Customers say

Overall, the Toyota Highlander has built a strong reputation across its model years for reliability, comfort, and family-friendly features. Drivers appreciate its spacious interiors and smooth rides, often highlighting its impressive safety features as a key asset. Many also enjoy the performance and power of the engines. However, some common criticisms include a lack of advanced infotainment options in older models, tight third-row seating, and varying cargo space depending on configuration. Overall, the Highlander is seen as a dependable choice for families and an excellent value in the SUV market.

AI generated from the text of customer reviews.

What people say

cargo space comfort interior performance safety

Julie W

5.0

Reviewed a 2021 Toyota Highlander on Jul 20, 2024

I loved my Highlander. I give my 2021 Toyota Highlander a 100 out of 10 on its safety. My car was a limited and it had most bells and whistles which I loved but what I loved most was that we all walked away from a collision where we were traveling 40 miles an hour and thanks to the safety design , we’re here.

Melissa C

5.0

Reviewed a 2021 Toyota Highlander on May 05, 2024

Toyota knocked it out of the park again with this 2021 Highlander Platinum. Luxurious quiet ride Lexus feel like. Very happy with this purchase.

Emmanuel S

5.0

Reviewed a 2022 Toyota Highlander on Apr 18, 2024

The car is great with very nice features. It is a good value in terms of price and nothing is missing. It is a good looking car

Anonymous

5.0

Reviewed a 2019 Toyota Highlander on Sep 03, 2024

great combination of reliability, function and features and price. Has more than enough bells and whistles with great driveability and comfort

James S

4.0

Reviewed a 2008 Toyota Highlander on Jul 16, 2024

We own 2 of these. One is the limited and the other is the all wheel drive. Over 150,000 on each and really just general maintenance issues so far with each. The clear coat is peeling and fading on the rear valance of each and the shocks and struts need to be replaced at this age. We have taken our limited everywhere including Texas, Colorado, North Carolina, Maryland, West Virginia, and more. Very good for families or dog owners and flexible with the third row seating. No major issues with either one so far!

Toyota Highlander FAQs

How much does the Toyota Highlander cost in Chicago, IL?

The average Toyota Highlander costs about $26,705.26. The average price has decreased by -7.5% since last year. The 376 for sale near Chicago, IL on CarGurus, range from $1,800 to $53,998 in price.

How many Toyota Highlander vehicles in Chicago, IL have no reported accidents or damage?

376 out of 376 for sale near Chicago, IL have no reported accidents or damage.

What fuel types are available?

Gasoline engines are available.