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

Price Range

$0 $60,000+

Max Mileage

New $80,000+

MPG

Min 14 Max 50

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640 Results for

Used Toyota Highlander For Sale in Chicago, IL

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

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

  • Get Directions
$35,294

2014 Toyota Highlander Limited

10,448 miles Lincolnwood, IL

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

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

  • Call Dealer
  • Get Directions
$33,000

2015 Toyota Highlander Limited

28,924 miles Joliet, IL

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

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

  • Call Dealer
  • Get Directions
$32,000

2015 Toyota Highlander XLE

23,354 miles Joliet, IL

Photo 1: Predawn Gray Mica 2016 Toyota Highlander XLE in Joliet, IL exterior view from front driver's side
Photo 2: Predawn Gray Mica 2016 Toyota Highlander XLE in Joliet, IL
Photo 3: interior dashboard and console 2016 Toyota Highlander XLE in Joliet, IL
Photo 4: cockpit view from driver’s seat 2016 Toyota Highlander XLE in Joliet, IL
Photo 5: 2016 Toyota Highlander XLE with  in Joliet, IL

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

  • Call Dealer
  • Get Directions
$34,100

2016 Toyota Highlander XLE

8,789 miles Joliet, IL

Photo 1: Ooh La La Rouge Mica 2015 Toyota Highlander LE Plus in Joliet, IL exterior view from front driver's side
Photo 2: Ooh La La Rouge Mica 2015 Toyota Highlander LE Plus in Joliet, IL
Photo 3: interior dashboard and console 2015 Toyota Highlander LE Plus in Joliet, IL
Photo 4: cockpit view from driver’s seat 2015 Toyota Highlander LE Plus in Joliet, IL
Photo 5: 2015 Toyota Highlander LE Plus with  in Joliet, IL

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

  • Call Dealer
  • Get Directions
$26,800

2015 Toyota Highlander LE Plus

40,050 miles Joliet, IL

Photo 1: Classic Silver Metallic 2012 Toyota Highlander SE in Joliet, IL exterior view from front driver's side
Photo 2: Classic Silver Metallic 2012 Toyota Highlander SE in Joliet, IL
Photo 3: interior dashboard and console 2012 Toyota Highlander SE in Joliet, IL
Photo 4: cockpit view from driver’s seat 2012 Toyota Highlander SE in Joliet, IL
Photo 5: Classic Silver Metallic 2012 Toyota Highlander SE in Joliet, IL front view of grill, headlights, hood and windshield

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

  • Call Dealer
  • Get Directions
$18,500

2012 Toyota Highlander SE

88,223 miles Joliet, IL

Photo 1: Classic Silver 2012 Toyota Highlander Limited in Forest Park, IL exterior view from front driver's side
Photo 2: Classic Silver 2012 Toyota Highlander Limited in Forest Park, IL
Photo 3: interior dashboard and console 2012 Toyota Highlander Limited in Forest Park, IL
Photo 4: cockpit view from driver’s seat 2012 Toyota Highlander Limited in Forest Park, IL
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
$25,377

2012 Toyota Highlander Limited

24,959 miles Forest Park, IL

Photo 1:  2013 Toyota Highlander Limited in Elmhurst, IL exterior view from front driver's side
Photo 2:  2013 Toyota Highlander Limited in Elmhurst, IL
Photo 3: interior dashboard and console 2013 Toyota Highlander Limited in Elmhurst, IL
Photo 4: cockpit view from driver’s seat 2013 Toyota Highlander Limited in Elmhurst, IL
Photo 5: 2013 Toyota Highlander Limited with  in Elmhurst, IL

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

  • Call Dealer
  • Get Directions
$21,293

2013 Toyota Highlander Limited

81,212 miles Elmhurst, IL

Photo 1:  2010 Toyota Highlander Limited in North Aurora, IL exterior view from front driver's side
Photo 2:  2010 Toyota Highlander Limited in North Aurora, IL
Photo 3: interior dashboard and console 2010 Toyota Highlander Limited in North Aurora, IL
Photo 4: cockpit view from driver’s seat 2010 Toyota Highlander Limited in North Aurora, IL
Photo 5: 2010 Toyota Highlander Limited with  in North Aurora, IL

Automatic / 4WD / 6 Cyl
17 mpg city / 23 mpg hwy

  • Call Dealer
  • Get Directions
$17,450

2010 Toyota Highlander Limited

62,152 miles North Aurora, IL

Photo 1: Magnetic Gray Metallic 2012 Toyota Highlander SE in Schaumburg, IL exterior view from front driver's side
Photo 2: Magnetic Gray Metallic 2012 Toyota Highlander SE in Schaumburg, IL
Photo 3: interior dashboard and console 2012 Toyota Highlander SE in Schaumburg, IL
Photo 4: cockpit view from driver’s seat 2012 Toyota Highlander SE in Schaumburg, IL
Photo 5: Magnetic Gray Metallic 2012 Toyota Highlander SE in Schaumburg, IL front view of grill, headlights, hood and windshield

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

  • Call Dealer
  • Get Directions
$19,999

2012 Toyota Highlander SE

67,960 miles Schaumburg, IL

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

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

  • Call Dealer
  • Get Directions
$29,000

2015 Toyota Highlander XLE

46,035 miles Chicago, IL

Automatic / FWD / 6 Cyl
17 mpg city / 21 mpg hwy

  • Call Dealer
  • Get Directions
$6,941

2003 Toyota Highlander

127,641 miles Forest Park, IL

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

  • Call Dealer
  • Get Directions
$28,994

2013 Toyota Highlander Limited

41,867 miles Chicago, IL

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

  • Call Dealer
  • Get Directions
Not Priced

2015 Toyota Highlander XLE

22,694 miles Saint Charles, IL

Photo 1: Midnight Black Metallic 2017 Toyota Highlander LE in Crystal Lake, IL exterior view from front driver's side
Photo 2: Midnight Black Metallic 2017 Toyota Highlander LE in Crystal Lake, IL
Photo 3: interior dashboard and console 2017 Toyota Highlander LE in Crystal Lake, IL
Photo 4: cockpit view from driver’s seat 2017 Toyota Highlander LE in Crystal Lake, IL
Photo 5: 2017 Toyota Highlander LE with  in Crystal Lake, IL

Automatic / AWD / 6 Cyl
20 mpg city / 27 mpg hwy

  • Get Directions
$31,500

2017 Toyota Highlander LE

6,269 miles Crystal Lake, IL

Photo 1: Sandy Beach Metallic 2011 Toyota Highlander Base in Westmont, IL exterior view from front driver's side
Photo 2: Sandy Beach Metallic 2011 Toyota Highlander Base in Westmont, IL
Photo 3: interior dashboard and console 2011 Toyota Highlander Base in Westmont, IL
Photo 4: Sandy Beach Metallic 2011 Toyota Highlander Base in Westmont, IL front view of grill, headlights, hood and windshield
Photo 5: 2011 Toyota Highlander Base with  in Westmont, IL

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

  • Get Directions
$15,500

2011 Toyota Highlander Base

66,866 miles Westmont, IL

Photo 1: Predawn Gray Mica 2016 Toyota Highlander XLE in Bourbonnais, IL exterior view from front driver's side
Photo 2: Predawn Gray Mica 2016 Toyota Highlander XLE in Bourbonnais, IL
Photo 3: Predawn Gray Mica 2016 Toyota Highlander XLE in Bourbonnais, IL front view of grill, headlights, hood and windshield

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

  • Get Directions
$34,995

2016 Toyota Highlander XLE

21,026 miles Bourbonnais, IL

Photo 1: 2014 Toyota Highlander Limited with  in Westmont, IL
Photo 2: 2014 Toyota Highlander Limited with  in Westmont, IL
Photo 3: 2014 Toyota Highlander Limited with  in Westmont, IL
Photo 4: 2014 Toyota Highlander Limited with  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
$34,700

2014 Toyota Highlander Limited

20,322 miles Westmont, IL

Photo 1: 2014 Toyota Highlander Limited with  in Elmhurst, IL
Photo 2: 2014 Toyota Highlander Limited with  in Elmhurst, IL
Photo 3: 2014 Toyota Highlander Limited with  in Elmhurst, IL
Photo 4: 2014 Toyota Highlander Limited with  in Elmhurst, IL
Photo 5: 2014 Toyota Highlander Limited with  in Elmhurst, IL

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

  • Get Directions
$31,421

2014 Toyota Highlander Limited

34,765 miles Elmhurst, IL

Photo 1:  2011 Toyota Highlander Limited in Oak Park, IL exterior view from front driver's side
Photo 2:  2011 Toyota Highlander Limited in Oak Park, IL
Photo 3: interior dashboard and console 2011 Toyota Highlander Limited in Oak Park, IL
Photo 4: cockpit view from driver’s seat 2011 Toyota Highlander Limited in Oak Park, IL
Photo 5: 2011 Toyota Highlander Limited with  in Oak Park, IL

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

  • Get Directions
$20,163

2011 Toyota Highlander Limited

73,386 miles Oak Park, IL

Photo 1: 2011 Toyota Highlander Base with  in Hodgkins, IL
Photo 2: 2011 Toyota Highlander Base with  in Hodgkins, IL
Photo 3: 2011 Toyota Highlander Base with  in Hodgkins, IL
Photo 4: 2011 Toyota Highlander Base with  in Hodgkins, IL
Photo 5: 2011 Toyota Highlander Base with  in Hodgkins, IL

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

  • Get Directions
$15,980

2011 Toyota Highlander Base

103,381 miles Hodgkins, IL

Photo 1: 2003 Toyota Highlander with  in Palatine, IL
Photo 2: 2003 Toyota Highlander in Palatine, IL
Photo 3: 2003 Toyota Highlander in Palatine, IL
Photo 4: 2003 Toyota Highlander in Palatine, IL
Photo 5: 2003 Toyota Highlander in Palatine, IL

Automatic / 4WD / 6 Cyl
16 mpg city / 21 mpg hwy

  • Get Directions
$7,398

2003 Toyota Highlander

111,577 miles Palatine, IL

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

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

  • Get Directions
$26,500

2015 Toyota Highlander LE

30,482 miles Westmont, IL

Photo 1:  2016 Toyota Highlander XLE in Hodgkins, IL exterior view from front driver's side

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

  • Get Directions
$37,980

2016 Toyota Highlander XLE

8,976 miles Hodgkins, IL