• Limited
  • XLE
  • Base
  • LE
  • Sport
  • SE
  • Gasoline
  • MP3
  • Well-Equipped
  • 6 Cyl
  • Heated Seats
  • AWD
  • 4WD
  • Handsfree/Bluetooth Integration
  • One Owner
  • Rear-View Camera
  • Great Deal
  • Good Deal
  • Navigation System
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  • Silver
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  • Satellite Radio
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  • Lower Than Average Mileage
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  • 2016
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  • 4 Cyl
  • 2008
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  • Popular Model
  • 2017
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  • 2011
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  • 2012
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  • Fair Price
  • 2007
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  • Beige
  • 2004
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Price Range

$0 $60,000+

Max Mileage

New $80,000+

MPG

Min 14 Max 50

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569 Results for

Used Toyota Highlander For Sale in Chicago, IL

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Photo 1: 2015 Toyota Highlander XLE with  in Tinley Park, IL
Photo 2: 2015 Toyota Highlander XLE with  in Tinley Park, IL
Photo 3: 2015 Toyota Highlander XLE with  in Tinley Park, IL
Photo 4: 2015 Toyota Highlander XLE with  in Tinley Park, IL
Photo 5: 2015 Toyota Highlander XLE with  in Tinley Park, IL

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

  • Dealer Page
$32,998

2015 Toyota Highlander XLE

45,178 miles Tinley Park, IL

Photo 1:  2014 Toyota Highlander LE in Tinley Park, IL exterior view from front driver's side
Photo 2:  2014 Toyota Highlander LE in Tinley Park, IL
Photo 3:  2014 Toyota Highlander LE in Tinley Park, IL front view of grill, headlights, hood and windshield
Photo 4:  2014 Toyota Highlander LE in Tinley Park, IL exterior view of passenger side
Photo 5:  2014 Toyota Highlander LE in Tinley Park, IL exterior view from rear driver's side

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

  • Dealer Page
$25,998

2014 Toyota Highlander LE

31,046 miles Tinley Park, IL

Photo 1:  2006 Toyota Highlander in Oak Lawn, IL exterior view from front driver's side
Photo 2:  2006 Toyota Highlander in Oak Lawn, IL
Photo 3:  2006 Toyota Highlander in Oak Lawn, IL front view of grill, headlights, hood and windshield
Photo 4:  2006 Toyota Highlander in Oak Lawn, IL exterior view of passenger side
Photo 5:  2006 Toyota Highlander in Oak Lawn, IL exterior view from rear driver's side

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

  • Dealer Page
$14,599

2006 Toyota Highlander

54,280 miles Oak Lawn, IL

Photo 1:  2007 Toyota Highlander in Glencoe, IL exterior view from front driver's side
Photo 2:  2007 Toyota Highlander in Glencoe, IL
Photo 3:  2007 Toyota Highlander in Glencoe, IL front view of grill, headlights, hood and windshield
Photo 4:  2007 Toyota Highlander in Glencoe, IL exterior view of passenger side
Photo 5:  2007 Toyota Highlander in Glencoe, IL exterior view from rear driver's side

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

  • Dealer Page
$10,998

2007 Toyota Highlander

94,830 miles Glencoe, IL

Photo 1:  2014 Toyota Highlander XLE in Tinley Park, IL exterior view from front driver's side
Photo 2:  2014 Toyota Highlander XLE in Tinley Park, IL
Photo 3:  2014 Toyota Highlander XLE in Tinley Park, IL front view of grill, headlights, hood and windshield
Photo 4:  2014 Toyota Highlander XLE in Tinley Park, IL exterior view of passenger side
Photo 5: 2014 Toyota Highlander XLE with  in Tinley Park, IL

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

  • Dealer Page
$32,998

2014 Toyota Highlander XLE

19,197 miles Tinley Park, IL

Photo 1: 2013 Toyota Highlander Limited with  in Glencoe, IL
Photo 2: 2013 Toyota Highlander Limited with  in Glencoe, IL
Photo 3: 2013 Toyota Highlander Limited with  in Glencoe, IL
Photo 4: 2013 Toyota Highlander Limited with  in Glencoe, IL
Photo 5: 2013 Toyota Highlander Limited with  in Glencoe, IL

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

  • Dealer Page
$24,998

2013 Toyota Highlander Limited

90,470 miles Glencoe, IL

Photo 1:  2008 Toyota Highlander Limited in Glencoe, IL exterior view from front driver's side
Photo 2:  2008 Toyota Highlander Limited in Glencoe, IL
Photo 3:  2008 Toyota Highlander Limited in Glencoe, IL front view of grill, headlights, hood and windshield
Photo 4:  2008 Toyota Highlander Limited in Glencoe, IL exterior view of passenger side
Photo 5:  2008 Toyota Highlander Limited in Glencoe, IL exterior view from rear driver's side

Automatic / 4WD / 6 Cyl
27 mpg city / 25 mpg hwy

  • Dealer Page
$23,599

2008 Toyota Highlander Limited

38,254 miles Glencoe, IL

Photo 1: 2010 Toyota Highlander Limited with  in Oak Park, IL
Photo 2: 2010 Toyota Highlander Limited with  in Oak Park, IL
Photo 3: 2010 Toyota Highlander Limited with  in Oak Park, IL
Photo 4: 2010 Toyota Highlander Limited with  in Oak Park, IL
Photo 5: 2010 Toyota Highlander Limited with  in Oak Park, IL

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

  • Get Directions
$18,295

2010 Toyota Highlander Limited

83,935 miles Oak Park, IL

Photo 1: 2010 Toyota Highlander SE with  in Northbrook, IL
Photo 2: 2010 Toyota Highlander SE with  in Northbrook, IL
Photo 3: 2010 Toyota Highlander SE with  in Northbrook, IL
Photo 4: 2010 Toyota Highlander SE with  in Northbrook, IL
Photo 5: 2010 Toyota Highlander SE with  in Northbrook, IL

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

  • Call Dealer
  • Get Directions
$13,599

2010 Toyota Highlander SE

98,162 miles Northbrook, IL

Photo 1: Silver Sky Metallic 2014 Toyota Highlander Limited in Northbrook, IL exterior view from front driver's side
Photo 2: Silver Sky Metallic 2014 Toyota Highlander Limited in Northbrook, IL
Photo 3: cockpit view from driver’s seat 2014 Toyota Highlander Limited in Northbrook, IL
Photo 4: Silver Sky Metallic 2014 Toyota Highlander Limited in Northbrook, IL closeup view of wheel
Photo 5: Silver Sky Metallic 2014 Toyota Highlander Limited in Northbrook, IL front view of grill, headlights, hood and windshield

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

  • Call Dealer
  • Get Directions
$31,371

2014 Toyota Highlander Limited

31,369 miles Northbrook, IL

Photo 1: Magnetic Gray Metallic 2013 Toyota Highlander Limited in Naperville, IL
Photo 2: 2013 Toyota Highlander Limited with  in Naperville, IL
Photo 3: 2013 Toyota Highlander Limited with  in Naperville, IL
Photo 4: Magnetic Gray Metallic 2013 Toyota Highlander Limited in Naperville, IL front view of grill, headlights, hood and windshield
Photo 5: Magnetic Gray Metallic 2013 Toyota Highlander Limited in Naperville, IL exterior view of passenger side

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

  • Call Dealer
  • Get Directions
$25,983

2013 Toyota Highlander Limited

48,540 miles Naperville, IL

Photo 1: Maroon 2012 Toyota Highlander in Naperville, IL exterior view from front driver's side

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

  • Call Dealer
  • Get Directions
$21,980

2012 Toyota Highlander

45,878 miles Naperville, IL

Photo 1: Predawn Gray Mica 2015 Toyota Highlander Limited in Downers Grove, IL exterior view from front driver's side
Photo 2: cockpit view from driver’s seat 2015 Toyota Highlander Limited in Downers Grove, IL
Photo 3: interior dashboard and console 2015 Toyota Highlander Limited in Downers Grove, IL
Photo 4: Predawn Gray Mica 2015 Toyota Highlander Limited in Downers Grove, IL front view of grill, headlights, hood and windshield
Photo 5: Predawn Gray Mica 2015 Toyota Highlander Limited in Downers Grove, IL exterior view of driver's side

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

  • Call Dealer
  • Get Directions
$34,894

2015 Toyota Highlander Limited

29,831 miles Downers Grove, IL

Photo 1: Beige/Tan 2009 Toyota Highlander Base in Elmhurst, IL exterior view from front driver's side
Photo 2: Beige/Tan 2009 Toyota Highlander Base in Elmhurst, IL
Photo 3: interior dashboard and console 2009 Toyota Highlander Base in Elmhurst, IL
Photo 4: Beige/Tan 2009 Toyota Highlander Base in Elmhurst, IL exterior view from rear driver's side
Photo 5: Beige/Tan 2009 Toyota Highlander Base in Elmhurst, IL exterior view from rear passenger side

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

  • Get Directions
$12,995

2009 Toyota Highlander Base

75,700 miles Elmhurst, IL

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

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

  • Call Dealer
  • Get Directions
$21,996

2013 Toyota Highlander SE

90,100 miles Channahon, IL

Photo 1: 2015 Toyota Highlander Limited Platinum with  in Northbrook, IL
Photo 2: 2015 Toyota Highlander Limited Platinum with  in Northbrook, IL
Photo 3: 2015 Toyota Highlander Limited Platinum with  in Northbrook, IL
Photo 4: 2015 Toyota Highlander Limited Platinum with  in Northbrook, IL
Photo 5: 2015 Toyota Highlander Limited Platinum with  in Northbrook, IL

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

  • Call Dealer
  • Get Directions
$32,988

2015 Toyota Highlander Limited Platinum

50,214 miles Northbrook, IL

Photo 1: 2016 Toyota Highlander XLE with  in Joliet, IL
Photo 2: 2016 Toyota Highlander XLE with  in Joliet, IL
Photo 3: 2016 Toyota Highlander XLE with  in Joliet, IL
Photo 4: 2016 Toyota Highlander XLE with  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
$37,000

2016 Toyota Highlander XLE

8,789 miles Joliet, IL

Photo 1:  2006 Toyota Highlander Limited in Chicago, IL
Photo 2: cockpit view from driver’s seat 2006 Toyota Highlander Limited in Chicago, IL
Photo 3: 2006 Toyota Highlander Limited with  in Chicago, IL
Photo 4:  2006 Toyota Highlander Limited in Chicago, IL exterior view of passenger side
Photo 5:  2006 Toyota Highlander Limited in Chicago, IL exterior view of driver's side

Automatic / FWD / 6 Cyl
28 mpg city / 25 mpg hwy

  • Call Dealer
  • Get Directions
$9,741

2006 Toyota Highlander Limited

103,092 miles Chicago, IL

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

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

  • Call Dealer
  • Get Directions
$35,500

2015 Toyota Highlander Limited

28,924 miles Joliet, IL

Photo 1: Nautical Blue Metallic 2013 Toyota Highlander Limited in Highland, IN exterior view from front driver's side
Photo 2: Nautical Blue Metallic 2013 Toyota Highlander Limited in Highland, IN
Photo 3: cockpit view from driver’s seat 2013 Toyota Highlander Limited in Highland, IN
Photo 4: interior dashboard and console 2013 Toyota Highlander Limited in Highland, IN
Photo 5: interior dashboard and console 2013 Toyota Highlander Limited in Highland, IN

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

  • Get Directions
$27,300

2013 Toyota Highlander Limited

31,832 miles Highland, IN

Photo 1: 2012 Toyota Highlander with  in Elmhurst, IL
Photo 2: 2012 Toyota Highlander with  in Elmhurst, IL
Photo 3: 2012 Toyota Highlander in Elmhurst, IL
Photo 4: 2012 Toyota Highlander in Elmhurst, IL
Photo 5: 2012 Toyota Highlander in Elmhurst, IL

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

  • Call Dealer
  • Get Directions
$15,995

2012 Toyota Highlander

126,154 miles Elmhurst, IL

Photo 1: Celestial Silver Metallic 2017 Toyota Highlander Limited in Elgin, IL exterior view from front driver's side
Photo 2: Celestial Silver Metallic 2017 Toyota Highlander Limited in Elgin, IL
Photo 3: cockpit view from driver’s seat 2017 Toyota Highlander Limited in Elgin, IL
Photo 4: Celestial Silver Metallic 2017 Toyota Highlander Limited in Elgin, IL exterior view of driver's side
Photo 5: Celestial Silver Metallic 2017 Toyota Highlander Limited in Elgin, IL front view of grill, headlights, hood and windshield

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

  • Call Dealer
  • Get Directions
$38,490

2017 Toyota Highlander Limited

5,985 miles Elgin, IL

Photo 1:  2012 Toyota Highlander in Valparaiso, IN exterior view from front driver's side
Photo 2:  2012 Toyota Highlander in Valparaiso, IN
Photo 3: cockpit view from driver’s seat 2012 Toyota Highlander in Valparaiso, IN
Photo 4: interior dashboard and console 2012 Toyota Highlander in Valparaiso, IN
Photo 5:  2012 Toyota Highlander in Valparaiso, IN exterior view from rear driver's side

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

  • Call Dealer
  • Get Directions
$17,553

2012 Toyota Highlander

60,727 miles Valparaiso, IN

Photo 1: 2008 Toyota Highlander Base with  in Northbrook, IL
Photo 2: 2008 Toyota Highlander Base with  in Northbrook, IL
Photo 3: 2008 Toyota Highlander Base with  in Northbrook, IL
Photo 4: 2008 Toyota Highlander Base with  in Northbrook, IL
Photo 5: 2008 Toyota Highlander Base with  in Northbrook, IL

Automatic / 4WD / 6 Cyl
27 mpg city / 25 mpg hwy

  • Call Dealer
  • Get Directions
$10,648

2008 Toyota Highlander Base

135,998 miles Northbrook, IL