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Used Toyota Highlander in Chicago, IL for Sale

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2019 Toyota
Highlander

$26,998* 38K miles
CarMax Hillside (Eisenhower Expy)
Available at your store - Chicago, IL
Available at your store - Chicago, IL
Key Features
Location: CarMax Hillside (Eisenhower Expy) in Chicago, Illinois 60162
Description: Used 2019 Toyota Highlander LE for sale - $26,998, 38,307 miles with Auto Cruise Control, 4WD/AWD, Rear View Camera, 3rd Rear Seat, Fold-Away Third Row, Auxiliary Audio Input
Transmission: Automatic Color:Silver Interior Color: Gray Average Vehicle Review: (4.75 reviews) Although this car was 5 years old when I purchased it, it had less than 30,000 miles and looked and drove like brand new. It is by far the nicest car I have ever owned; some people have their Cadillacs or Mercedes, I have my Toyota. It's a good thing it has cruise control because it rides so smooth down the highway you can hit 90 without realizing it. I had it in for an oil change and the guys in the shop told me you can't go wrong with a Highlander. It is really quiet, smooth riding, and actually gets great gas mileage for a vehicle its size (around 24 MPG city/freeway). The second row seats are incredibly roomy even for a full grown adult. The quality interior looks classy and has no annoying rattles or squeaks.

2009 Toyota
Highlander

$15,998* 93K miles
CarMax Schaumburg
Free Transfer to your store - IL to IL
Free Transfer to your store - IL to IL
Key Features
Location: CarMax Schaumburg in Chicago, Illinois 60173
Description: Used 2009 Toyota Highlander Limited for sale - $15,998, 93,992 miles with Power Liftgate/DeckLid, 4WD/AWD, Leather Seats, JBL Sound System, Satellite Radio Ready, Rear View Camera
Transmission: Automatic Color:Black Interior Color: Tan Average Vehicle Review: (4.684 reviews) I have had 3 Toyota trucks over the years. Never had any trouble with any of them. Easy to drive stick and/or automatic, gas mileage was great. This time I decided to go with a CUV which is a cross-over from a car and SUV. Had to get used to the color which is Sunfire (redish). Never realized how many red vehicles there were out there until I got mine. It handles so easy. I love it. Couldn't be happier.

2019 Toyota
Highlander

$25,998* 42K miles
CarMax Schaumburg
Free Transfer to your store - IL to IL
Free Transfer to your store - IL to IL
Key Features
Location: CarMax Schaumburg in Chicago, Illinois 60173
Description: Used 2019 Toyota Highlander LE for sale - $25,998, 42,237 miles with Auto Cruise Control, 4WD/AWD, Rear View Camera, 3rd Rear Seat, Fold-Away Third Row, Auxiliary Audio Input
Transmission: Automatic Color:Black Interior Color: Gray Average Vehicle Review: (4.75 reviews) This is the third Highlander I've leased and the 2014 redesigned model has more features and has better styling than previous versions. This SVU is a dream to drive--quiet, smooth, easy to handle and great pick up when you need it--on the highway or around town. I've taken my 16 year old granddaughter for driving practice, and her comment was that the "car helped her to drive". My only negative is the tires that came on the car, while giving a great ride, did not last long. I've replaced them with better wearing tires.

2019 Toyota
Highlander

$27,998* 31K miles
CarMax Schaumburg
Free Transfer to your store - IL to IL
Free Transfer to your store - IL to IL
Key Features
Location: CarMax Schaumburg in Chicago, Illinois 60173
Description: Used 2019 Toyota Highlander LE for sale - $27,998, 31,877 miles with Auto Cruise Control, 4WD/AWD, Rear View Camera, 3rd Rear Seat, Fold-Away Third Row, Auxiliary Audio Input
Transmission: Automatic Color:Gray Interior Color: Black Average Vehicle Review: (4.75 reviews)

2019 Toyota
Highlander

$28,998* 30K miles
CarMax Schaumburg
Free Transfer to your store - IL to IL
Free Transfer to your store - IL to IL
Key Features
Location: CarMax Schaumburg in Chicago, Illinois 60173
Description: Used 2019 Toyota Highlander LE for sale - $28,998, 30,048 miles with Auto Cruise Control, 4WD/AWD, Rear View Camera, 3rd Rear Seat, Fold-Away Third Row, Auxiliary Audio Input
Transmission: Automatic Color:Gray Interior Color: Gray Average Vehicle Review: (4.75 reviews)

2019 Toyota
Highlander

$26,998* 26K miles
CarMax Schaumburg
Free Transfer to your store - IL to IL
Free Transfer to your store - IL to IL
Key Features
Location: CarMax Schaumburg in Chicago, Illinois 60173
Description: Used 2019 Toyota Highlander LE for sale - $26,998, 26,792 miles with Auto Cruise Control, Rear View Camera, 3rd Rear Seat, Fold-Away Third Row, Auxiliary Audio Input, Alloy Wheels
Transmission: Automatic Color:Silver Interior Color: Black Average Vehicle Review: (4.75 reviews)

2016 Toyota
Highlander

$28,998* 20K miles
CarMax Schaumburg
Free Transfer to your store - IL to IL
Free Transfer to your store - IL to IL
Key Features
Location: CarMax Schaumburg in Chicago, Illinois 60173
Description: Used 2016 Toyota Highlander XLE for sale - $28,998, 20,105 miles with Power Liftgate/DeckLid, 4WD/AWD, Leather Seats, Satellite Radio Ready, Rear View Camera, 3rd Rear Seat
Transmission: Automatic Color:White Interior Color: White Average Vehicle Review: (4.75 reviews)

2014 Toyota
Highlander

$21,998* 42K miles
CarMax Naperville
Free Transfer to your store - IL to IL
Free Transfer to your store - IL to IL
Key Features
Location: CarMax Naperville in Naperville, Illinois 60563
Description: Used 2014 Toyota Highlander LE PLUS for sale - $21,998, 42,909 miles with Power Liftgate/DeckLid, Satellite Radio Ready, Rear View Camera, 3rd Rear Seat, Fold-Away Third Row, Auxiliary Audio Input
Transmission: Automatic Color:Black Interior Color: Gray Average Vehicle Review: (4.571 reviews)

2017 Toyota
Highlander

$32,998* 34K miles
CarMax Naperville
Coming Soon to Naperville, IL
Coming Soon to Naperville, IL
Key Features
Location: CarMax Naperville in Naperville, Illinois 60563
Description: Used 2017 Toyota Highlander Limited for sale - $32,998, 34,262 miles with Power Liftgate/DeckLid, Auto Cruise Control, 4WD/AWD, Leather Seats, JBL Sound System, Satellite Radio Ready
Transmission: Automatic Color:Black Interior Color: Black Average Vehicle Review: (5 reviews)

2017 Toyota
Highlander

$34,998* 21K miles
CarMax Naperville
Free Transfer to your store - IL to IL
Free Transfer to your store - IL to IL
Key Features
Location: CarMax Naperville in Naperville, Illinois 60563
Description: Used 2017 Toyota Highlander Limited for sale - $34,998, 21,627 miles with Power Liftgate/DeckLid, Auto Cruise Control, 4WD/AWD, Leather Seats, JBL Sound System, Satellite Radio Ready
Transmission: Automatic Color:Black Interior Color: Tan Average Vehicle Review: (5 reviews)

2017 Toyota
Highlander

$26,998* 27K miles
CarMax Naperville
Free Transfer to your store - IL to IL
Free Transfer to your store - IL to IL
Key Features
Location: CarMax Naperville in Naperville, Illinois 60563
Description: Used 2017 Toyota Highlander LE PLUS for sale - $26,998, 27,046 miles with Power Liftgate/DeckLid, Auto Cruise Control, 4WD/AWD, Satellite Radio Ready, Rear View Camera, 3rd Rear Seat
Transmission: Automatic Color:Red Interior Color: Gray Average Vehicle Review: (5 reviews)

2019 Toyota
Highlander

$24,998* 39K miles
CarMax Glencoe (Edens Expy)
Free Transfer to your store - IL to IL
Free Transfer to your store - IL to IL
Key Features
Location: CarMax Glencoe (Edens Expy) in Glencoe, Illinois 60022
Description: Used 2019 Toyota Highlander LE for sale - $24,998, 39,629 miles with Auto Cruise Control, 4WD/AWD, Rear View Camera, 3rd Rear Seat, Fold-Away Third Row, Auxiliary Audio Input
Transmission: Automatic Color:Silver Interior Color: Black Average Vehicle Review: (4.75 reviews)

2016 Toyota
Highlander

$20,998* 87K miles
CarMax Glencoe (Edens Expy)
Free Transfer to your store - IL to IL
Free Transfer to your store - IL to IL
Key Features
Location: CarMax Glencoe (Edens Expy) in Glencoe, Illinois 60022
Description: Used 2016 Toyota Highlander LE PLUS for sale - $20,998, 87,424 miles with Power Liftgate/DeckLid, 4WD/AWD, Satellite Radio Ready, Rear View Camera, 3rd Rear Seat, Fold-Away Third Row
Transmission: Automatic Color:Black Interior Color: Black Average Vehicle Review: (4.75 reviews)

2016 Toyota
Highlander

$25,998* 44K miles
CarMax Oak Lawn
Free Transfer to your store - IL to IL
Free Transfer to your store - IL to IL
Key Features
Location: CarMax Oak Lawn in Chicago, Illinois 60453
Description: Used 2016 Toyota Highlander XLE for sale - $25,998, 44,484 miles with Power Liftgate/DeckLid, 4WD/AWD, Leather Seats, Satellite Radio Ready, Rear View Camera, 3rd Rear Seat
Transmission: Automatic Color:Blue Interior Color: Gray Average Vehicle Review: (4.75 reviews)

2014 Toyota
Highlander

$20,998* 51K miles
CarMax Tinley Park
Free Transfer to your store - IL to IL
Free Transfer to your store - IL to IL
Key Features
Location: CarMax Tinley Park in Chicago, Illinois 60477
Description: Used 2014 Toyota Highlander LE for sale - $20,998, 51,253 miles with Rear View Camera, 3rd Rear Seat, Fold-Away Third Row, Auxiliary Audio Input, Cruise Control, Alloy Wheels
Transmission: Automatic Color:Black Interior Color: Black Average Vehicle Review: (4.571 reviews)

2019 Toyota
Highlander

$26,998* 36K miles
CarMax Tinley Park
Free Transfer to your store - IL to IL
Free Transfer to your store - IL to IL
Key Features
Location: CarMax Tinley Park in Chicago, Illinois 60477
Description: Used 2019 Toyota Highlander LE for sale - $26,998, 36,760 miles with Auto Cruise Control, 4WD/AWD, Rear View Camera, 3rd Rear Seat, Fold-Away Third Row, Auxiliary Audio Input
Transmission: Automatic Color:Silver Interior Color: Gray Average Vehicle Review: (4.75 reviews)

2019 Toyota
Highlander

$27,998* 30K miles
CarMax Tinley Park
Free Transfer to your store - IL to IL
Free Transfer to your store - IL to IL
Key Features
Location: CarMax Tinley Park in Chicago, Illinois 60477
Description: Used 2019 Toyota Highlander LE for sale - $27,998, 30,310 miles with Auto Cruise Control, 4WD/AWD, Rear View Camera, 3rd Rear Seat, Fold-Away Third Row, Auxiliary Audio Input
Transmission: Automatic Color:Silver Interior Color: Gray Average Vehicle Review: (4.75 reviews)

2018 Toyota
Highlander

$31,998* 35K miles
CarMax Tinley Park
Free Transfer to your store - IL to IL
Free Transfer to your store - IL to IL
Key Features
Location: CarMax Tinley Park in Chicago, Illinois 60477
Description: Used 2018 Toyota Highlander XLE for sale - $31,998, 35,537 miles with Power Liftgate/DeckLid, Auto Cruise Control, 4WD/AWD, Leather Seats, Satellite Radio Ready, Rear View Camera
Transmission: Automatic Color:White Interior Color: Black Average Vehicle Review: (5 reviews)

2016 Toyota
Highlander

$25,998* 39K miles
CarMax Tinley Park
Free Transfer to your store - IL to IL
Free Transfer to your store - IL to IL
Key Features
Location: CarMax Tinley Park in Chicago, Illinois 60477
Description: Used 2016 Toyota Highlander XLE for sale - $25,998, 39,068 miles with Power Liftgate/DeckLid, 4WD/AWD, Leather Seats, Satellite Radio Ready, Rear View Camera, 3rd Rear Seat
Transmission: Automatic Color:Silver Interior Color: Black Average Vehicle Review: (4.75 reviews)

2019 Toyota
Highlander

$28,998* 21K miles
CarMax Merrillville
Free Transfer to your store - IN to IL
Free Transfer to your store - IN to IL
Key Features
Location: CarMax Merrillville in Merrillville, Indiana 46410
Description: Used 2019 Toyota Highlander LE for sale - $28,998, 21,257 miles with Auto Cruise Control, 4WD/AWD, Rear View Camera, 3rd Rear Seat, Fold-Away Third Row, Auxiliary Audio Input
Transmission: Automatic Color:Black Interior Color: Gray Average Vehicle Review: (4.75 reviews)

2016 Toyota
Highlander

$26,998* 22K miles
CarMax Merrillville
Free Transfer to your store - IN to IL
Free Transfer to your store - IN to IL
Key Features
Location: CarMax Merrillville in Merrillville, Indiana 46410
Description: Used 2016 Toyota Highlander XLE for sale - $26,998, 22,598 miles with Power Liftgate/DeckLid, 4WD/AWD, Leather Seats, Satellite Radio Ready, Rear View Camera, 3rd Rear Seat
Transmission: Automatic Color:Blue Interior Color: Gray Average Vehicle Review: (4.75 reviews)

2020 Toyota
Highlander

MSRP $50,788* New
CarMax Kenosha
Available in Kenosha, WI
Available in Kenosha, WI
Key Features
Location: CarMax Kenosha in Kenosha, Wisconsin 53142
Description: New 2020 Toyota Highlander Limited Platinum for sale - $50,788, 5 miles with Power Liftgate/DeckLid, Auto Cruise Control, 4WD/AWD, Leather Seats, JBL Sound System, Satellite Radio Ready
Transmission: Automatic Color: Interior Color: Average Vehicle Review: (0 reviews)

Reviews for Toyota Highlander

Overall Rating

4.7 out of 5(402 reviews)

Highlander - Super Great

I have had 3 Toyota trucks over the years. Never had any trouble with any of them. Easy to drive stick and/or automatic, gas mileage was great. This time I decided to go with a CUV which is a cross-over from a car and SUV. Had to get used to the color which is Sunfire (redish). Never realized how many red vehicles there were out there until I got mine. It handles so easy. I love it. Couldn't be happier.

- DJ Duvall, 2006 Toyota Highlander

Nicest car I have ever owned

Although this car was 5 years old when I purchased it, it had less than 30,000 miles and looked and drove like brand new. It is by far the nicest car I have ever owned; some people have their Cadillacs or Mercedes, I have my Toyota. It's a good thing it has cruise control because it rides so smooth down the highway you can hit 90 without realizing it. I had it in for an oil change and the guys in the shop told me you can't go wrong with a Highlander. It is really quiet, smooth riding, and actually gets great gas mileage for a vehicle its size (around 24 MPG city/freeway). The second row seats are incredibly roomy even for a full grown adult. The quality interior looks classy and has no annoying rattles or squeaks.

- Gerald Smith, 2009 Toyota Highlander

Best Highlander I've had

This is the third Highlander I've leased and the 2014 redesigned model has more features and has better styling than previous versions. This SVU is a dream to drive--quiet, smooth, easy to handle and great pick up when you need it--on the highway or around town. I've taken my 16 year old granddaughter for driving practice, and her comment was that the "car helped her to drive". My only negative is the tires that came on the car, while giving a great ride, did not last long. I've replaced them with better wearing tires.

- Joy Curtis, 2014 Toyota Highlander

This price does not include tax, title, and tags. Additional fees may also apply depending on the state of purchase.