• Limited
  • XLE
  • LE
  • Base
  • SE
  • Sport
  • Gasoline
  • MP3
  • 6 Cyl
  • Heated Seats
  • Well-Equipped
  • AWD
  • Rear-View Camera
  • 4WD
  • Handsfree/Bluetooth Integration
  • One Owner
  • Great Deal
  • Navigation System
  • Average Supply
  • Sun/Moonroof
  • 2015
  • Black
  • FWD
  • 2016
  • Silver
  • Satellite Radio
  • Gray
  • White
  • 2013
  • Low Mileage
  • 4 Cyl
  • Blue
  • Good Deal
  • 2017
  • 2014
  • Hybrid
  • Certified Pre-Owned
  • 2012
  • 2008
  • Red
  • Green
  • Lower Than Average Mileage
  • Low Fuel Costs
  • 2010
  • 2009
  • 2011
  • 2006
  • 2005
  • 2007
  • 2003
  • Fair Price
  • Gold
  • 2004
  • Beige
  • 2002
  • Going Fast
  • 2001
  • 2018

Price Range

$0 $60,000+

Max Mileage

New $80,000+

MPG

Min 14 Max 50

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852 Results for

Used Toyota Highlander For Sale in Chicago, IL

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Photo 1:  2006 Toyota Highlander Base in Schaumburg, IL exterior view from front driver's side
Photo 2:  2006 Toyota Highlander Base in Schaumburg, IL
Photo 3: cockpit view from driver’s seat 2006 Toyota Highlander Base in Schaumburg, IL
Photo 4:  2006 Toyota Highlander Base in Schaumburg, IL front view of grill, headlights, hood and windshield
Photo 5: 2006 Toyota Highlander Base with  in Schaumburg, IL

Automatic / FWD / 4 Cyl
19 mpg city / 25 mpg hwy

  • Call Dealer
  • Get Directions
$8,900

2006 Toyota Highlander Base

97,357 miles Schaumburg, IL

Photo 1: Shoreline Blue Pearl 2014 Toyota Highlander Limited in Schaumburg, IL exterior view from front driver's side
Photo 2: Shoreline Blue Pearl 2014 Toyota Highlander Limited in Schaumburg, IL
Photo 3: interior dashboard and console 2014 Toyota Highlander Limited in Schaumburg, IL
Photo 4: cockpit view from driver’s seat 2014 Toyota Highlander Limited in Schaumburg, IL
Photo 5: 2014 Toyota Highlander Limited with  in Schaumburg, IL

Automatic / AWD / 6 Cyl
18 mpg city / 24 mpg hwy

  • Call Dealer
  • Get Directions
$26,550

2014 Toyota Highlander Limited

50,173 miles Schaumburg, IL

Photo 1: Blizzard Pearl 2015 Toyota Highlander Limited in Schaumburg, IL exterior view from front driver's side
Photo 2: Blizzard Pearl 2015 Toyota Highlander Limited in Schaumburg, IL
Photo 3: interior dashboard and console 2015 Toyota Highlander Limited in Schaumburg, IL
Photo 4: cockpit view from driver’s seat 2015 Toyota Highlander Limited in Schaumburg, IL
Photo 5: 2015 Toyota Highlander Limited with  in Schaumburg, IL

Automatic / AWD / 6 Cyl
18 mpg city / 24 mpg hwy

  • Call Dealer
  • Get Directions
$32,950

2015 Toyota Highlander Limited

22,439 miles Schaumburg, IL

Photo 1:  2006 Toyota Highlander in Schaumburg, IL exterior view from front driver's side
Photo 2:  2006 Toyota Highlander in Schaumburg, IL
Photo 3: cockpit view from driver’s seat 2006 Toyota Highlander in Schaumburg, IL
Photo 4:  2006 Toyota Highlander in Schaumburg, IL front view of grill, headlights, hood and windshield
Photo 5: 2006 Toyota Highlander with  in Schaumburg, IL

Automatic / FWD / 6 Cyl
17 mpg city / 23 mpg hwy

  • Call Dealer
  • Get Directions
$8,700

2006 Toyota Highlander

127,699 miles Schaumburg, IL

Photo 1:  2014 Toyota Highlander LE in Schaumburg, IL
Photo 2: interior dashboard and console 2014 Toyota Highlander LE in Schaumburg, IL
Photo 3: cockpit view from driver’s seat 2014 Toyota Highlander LE in Schaumburg, IL
Photo 4: 2014 Toyota Highlander LE with  in Schaumburg, IL
Photo 5: 2014 Toyota Highlander LE with  in Schaumburg, IL

Automatic / FWD / 4 Cyl
20 mpg city / 25 mpg hwy

  • Call Dealer
  • Get Directions
$22,995

2014 Toyota Highlander LE

43,922 miles Schaumburg, IL

Photo 1:  2012 Toyota Highlander Limited in Forest Park, IL
Photo 2: interior dashboard and console 2012 Toyota Highlander Limited in Forest Park, IL
Photo 3: 2012 Toyota Highlander Limited with  in Forest Park, IL
Photo 4:  2012 Toyota Highlander Limited in Forest Park, IL front view of grill, headlights, hood and windshield
Photo 5: 2012 Toyota Highlander Limited with  in Forest Park, IL

Automatic / 4WD / 6 Cyl
17 mpg city / 22 mpg hwy

  • Call Dealer
  • Get Directions
$19,900

2012 Toyota Highlander Limited

90,520 miles Forest Park, IL

Photo 1:  2013 Toyota Highlander in Forest Park, IL
Photo 2: interior dashboard and console 2013 Toyota Highlander in Forest Park, IL
Photo 3:  2013 Toyota Highlander in Forest Park, IL front view of grill, headlights, hood and windshield
Photo 4: 2013 Toyota Highlander with  in Forest Park, IL
Photo 5: 2013 Toyota Highlander with  in Forest Park, IL

Automatic / 4WD / 6 Cyl
17 mpg city / 22 mpg hwy

  • Call Dealer
  • Get Directions
$15,900

2013 Toyota Highlander

122,520 miles Forest Park, IL

Photo 1:  2012 Toyota Highlander Base in Schaumburg, IL exterior view from front driver's side
Photo 2:  2012 Toyota Highlander Base in Schaumburg, IL
Photo 3: interior dashboard and console 2012 Toyota Highlander Base in Schaumburg, IL
Photo 4: cockpit view from driver’s seat 2012 Toyota Highlander Base in Schaumburg, IL
Photo 5: 2012 Toyota Highlander Base with  in Schaumburg, IL

Automatic / FWD / 6 Cyl
18 mpg city / 24 mpg hwy

  • Call Dealer
  • Get Directions
$15,777

2012 Toyota Highlander Base

81,868 miles Schaumburg, IL

Automatic / FWD / 4 Cyl
20 mpg city / 25 mpg hwy

  • Call Dealer
  • Get Directions
$14,451

2012 Toyota Highlander Base

121,441 miles Schaumburg, IL

Automatic / AWD / 6 Cyl
18 mpg city / 24 mpg hwy

  • Call Dealer
  • Get Directions
$24,250

2014 Toyota Highlander XLE

75,847 miles Schaumburg, IL

Photo 1:  2012 Toyota Highlander SE in Westmont, IL exterior view from front driver's side
Photo 2:  2012 Toyota Highlander SE in Westmont, IL
Photo 3: interior dashboard and console 2012 Toyota Highlander SE in Westmont, IL
Photo 4: cockpit view from driver’s seat 2012 Toyota Highlander SE in Westmont, IL
Photo 5: 2012 Toyota Highlander SE with  in Westmont, IL

Automatic / 4WD / 6 Cyl
17 mpg city / 22 mpg hwy

  • Get Directions
$17,999

2012 Toyota Highlander SE

72,586 miles Westmont, IL

Photo 1: Blizzard Pearl 2015 Toyota Highlander XLE in Westmont, IL exterior view from front driver's side
Photo 2: Blizzard Pearl 2015 Toyota Highlander XLE in Westmont, IL
Photo 3: interior dashboard and console 2015 Toyota Highlander XLE in Westmont, IL
Photo 4: cockpit view from driver’s seat 2015 Toyota Highlander XLE in Westmont, IL
Photo 5: 2015 Toyota Highlander XLE with  in Westmont, IL

Automatic / AWD / 6 Cyl
18 mpg city / 24 mpg hwy

  • Get Directions
$31,800

2015 Toyota Highlander XLE

30,516 miles Westmont, IL

Photo 1: 2004 Toyota Highlander with  in Naperville, IL
Photo 2: 2004 Toyota Highlander in Naperville, IL
Photo 3: 2004 Toyota Highlander in Naperville, IL
Photo 4: 2004 Toyota Highlander in Naperville, IL
Photo 5: 2004 Toyota Highlander in Naperville, IL

Automatic / FWD / 4 Cyl
19 mpg city / 25 mpg hwy

  • Get Directions
$8,856

2004 Toyota Highlander

99,019 miles Naperville, IL

Photo 1: Nautical Blue Metallic 2014 Toyota Highlander XLE in Westmont, IL exterior view from front driver's side
Photo 2: Nautical Blue Metallic 2014 Toyota Highlander XLE in Westmont, IL
Photo 3: interior dashboard and console 2014 Toyota Highlander XLE in Westmont, IL
Photo 4: cockpit view from driver’s seat 2014 Toyota Highlander XLE in Westmont, IL
Photo 5: 2014 Toyota Highlander XLE with  in Westmont, IL

Automatic / AWD / 6 Cyl
18 mpg city / 24 mpg hwy

  • Get Directions
$25,999

2014 Toyota Highlander XLE

46,254 miles Westmont, IL

Photo 1: 2015 Toyota Highlander LE with  in Saint Charles, IL
Photo 2: 2015 Toyota Highlander LE with  in Saint Charles, IL
Photo 3: 2015 Toyota Highlander LE with  in Saint Charles, IL
Photo 4: 2015 Toyota Highlander LE in Saint Charles, IL
Photo 5: 2015 Toyota Highlander LE in Saint Charles, IL

Automatic / AWD / 6 Cyl
18 mpg city / 24 mpg hwy

  • Get Directions
$26,917

2015 Toyota Highlander LE

34,592 miles Saint Charles, IL

Photo 1: Blizzard Pearl 2013 Toyota Highlander Limited in Gurnee, IL
Photo 2: 2013 Toyota Highlander Limited with  in Gurnee, IL
Photo 3: Blizzard Pearl 2013 Toyota Highlander Limited in Gurnee, IL front view of grill, headlights, hood and windshield
Photo 4: 2013 Toyota Highlander Limited with  in Gurnee, IL
Photo 5: 2013 Toyota Highlander Limited with  in Gurnee, IL

Automatic / 4WD / 6 Cyl
17 mpg city / 22 mpg hwy

  • Get Directions
$22,895

2013 Toyota Highlander Limited

67,500 miles Gurnee, IL

Photo 1: Shoreline Blue Pearl 2015 Toyota Highlander Limited Platinum in Schererville, IN exterior view from front driver's side
Photo 2: Shoreline Blue Pearl 2015 Toyota Highlander Limited Platinum in Schererville, IN
Photo 3: 2015 Toyota Highlander Limited Platinum with  in Schererville, IN
Photo 4: 2015 Toyota Highlander Limited Platinum with  in Schererville, IN
Photo 5: 2015 Toyota Highlander Limited Platinum with  in Schererville, IN

Automatic / AWD / 6 Cyl
18 mpg city / 24 mpg hwy

  • Get Directions
$34,471

2015 Toyota Highlander Limited Platinum

35,747 miles Schererville, IN

Photo 1:  2017 Toyota Highlander XLE in Matteson, IL exterior view from front driver's side
Photo 2:  2017 Toyota Highlander XLE in Matteson, IL
Photo 3: interior dashboard and console 2017 Toyota Highlander XLE in Matteson, IL
Photo 4: cockpit view from driver’s seat 2017 Toyota Highlander XLE in Matteson, IL
Photo 5: 2017 Toyota Highlander XLE with  in Matteson, IL

Automatic / AWD / 6 Cyl
19 mpg city / 26 mpg hwy

  • Get Directions
$34,411

2017 Toyota Highlander XLE

16,905 miles Matteson, IL

Photo 1: Attitude Black Metallic 2015 Toyota Highlander Limited Platinum in Chicago, IL exterior view from front driver's side
Photo 2: Attitude Black Metallic 2015 Toyota Highlander Limited Platinum in Chicago, IL
Photo 3: cockpit view from driver’s seat 2015 Toyota Highlander Limited Platinum in Chicago, IL
Photo 4: 2015 Toyota Highlander Limited Platinum with  in Chicago, IL
Photo 5: Attitude Black Metallic 2015 Toyota Highlander Limited Platinum in Chicago, IL front view of grill, headlights, hood and windshield

Automatic / AWD / 6 Cyl
18 mpg city / 24 mpg hwy

  • Get Directions
$30,997

2015 Toyota Highlander Limited Platinum

42,890 miles Chicago, IL

Photo 1: Attitude Black Metallic 2014 Toyota Highlander Limited in Westmont, IL exterior view from front driver's side
Photo 2: Attitude Black Metallic 2014 Toyota Highlander Limited in Westmont, IL
Photo 3: interior dashboard and console 2014 Toyota Highlander Limited in Westmont, IL
Photo 4: cockpit view from driver’s seat 2014 Toyota Highlander Limited in Westmont, IL
Photo 5: 2014 Toyota Highlander Limited with  in Westmont, IL

Automatic / AWD / 6 Cyl
18 mpg city / 24 mpg hwy

  • Get Directions
$29,999

2014 Toyota Highlander Limited

30,930 miles Westmont, IL

Photo 1: Blizzard Pearl 2016 Toyota Highlander Limited in Westmont, IL exterior view from front driver's side
Photo 2: Blizzard Pearl 2016 Toyota Highlander Limited in Westmont, IL
Photo 3: interior dashboard and console 2016 Toyota Highlander Limited in Westmont, IL
Photo 4: cockpit view from driver’s seat 2016 Toyota Highlander Limited in Westmont, IL
Photo 5: 2016 Toyota Highlander Limited with  in Westmont, IL

Automatic / AWD / 6 Cyl
18 mpg city / 24 mpg hwy

  • Get Directions
$33,999

2016 Toyota Highlander Limited

31,536 miles Westmont, IL

Photo 1: Blizzard Pearl 2017 Toyota Highlander XLE in Merrillville, IN
Photo 2: interior dashboard and console 2017 Toyota Highlander XLE in Merrillville, IN
Photo 3: cockpit view from driver’s seat 2017 Toyota Highlander XLE in Merrillville, IN
Photo 4: 2017 Toyota Highlander XLE with  in Merrillville, IN
Photo 5: Blizzard Pearl 2017 Toyota Highlander XLE in Merrillville, IN front view of grill, headlights, hood and windshield

Automatic / AWD / 6 Cyl
19 mpg city / 26 mpg hwy

  • Get Directions
$35,000

2017 Toyota Highlander XLE

10,675 miles Merrillville, IN

Photo 1: Oasis Green Pearl 2006 Toyota Highlander in Schaumburg, IL exterior view from front driver's side
Photo 2: Oasis Green Pearl 2006 Toyota Highlander in Schaumburg, IL
Photo 3: cockpit view from driver’s seat 2006 Toyota Highlander in Schaumburg, IL
Photo 4: 2006 Toyota Highlander with  in Schaumburg, IL
Photo 5: Oasis Green Pearl 2006 Toyota Highlander in Schaumburg, IL front view of grill, headlights, hood and windshield

Automatic / FWD / 4 Cyl
19 mpg city / 25 mpg hwy

  • Get Directions
$7,495

2006 Toyota Highlander

106,638 miles Schaumburg, IL

Photo 1: Attitude Black Metallic 2015 Toyota Highlander XLE in Westmont, IL exterior view from front driver's side
Photo 2: Attitude Black Metallic 2015 Toyota Highlander XLE in Westmont, IL
Photo 3: interior dashboard and console 2015 Toyota Highlander XLE in Westmont, IL
Photo 4: 2015 Toyota Highlander XLE with  in Westmont, IL
Photo 5: Attitude Black Metallic 2015 Toyota Highlander XLE in Westmont, IL front view of grill, headlights, hood and windshield

Automatic / AWD / 6 Cyl
18 mpg city / 24 mpg hwy

  • Get Directions
$30,794

2015 Toyota Highlander XLE

38,678 miles Westmont, IL