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Price Range

$0 $60,000+

Max Mileage

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623 Results for

Used Toyota Highlander For Sale in Chicago, IL

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

  • Dealer Page
  • Get Directions
$6,995

2002 Toyota Highlander

122,036 miles / Gardner, IL

Photo 1: 2014 Toyota Highlander Limited with  in Merrillville, IN
Photo 2: 2014 Toyota Highlander Limited with  in Merrillville, IN
Photo 3: 2014 Toyota Highlander Limited with  in Merrillville, IN
Photo 4: 2014 Toyota Highlander Limited with  in Merrillville, IN
Photo 5: 2014 Toyota Highlander Limited with  in Merrillville, IN

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

  • Call Dealer
  • Get Directions
$27,993

2014 Toyota Highlander Limited

83,670 miles / Merrillville, IN

Photo 1: Creme Brulee Mica 2014 Toyota Highlander XLE in Northbrook, IL exterior view from front driver's side
Photo 2: Creme Brulee Mica 2014 Toyota Highlander XLE in Northbrook, IL
Photo 3: cockpit view from driver’s seat 2014 Toyota Highlander XLE in Northbrook, IL
Photo 4: Creme Brulee Mica 2014 Toyota Highlander XLE in Northbrook, IL front view of grill, headlights, hood and windshield
Photo 5: Creme Brulee Mica 2014 Toyota Highlander XLE in Northbrook, IL exterior view from rear driver's side

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

  • Call Dealer
  • Get Directions
$31,991

2014 Toyota Highlander XLE

19,823 miles / Northbrook, IL

Photo 1: 2013 Toyota Highlander Base Plus with  in Naperville, IL
Photo 2: 2013 Toyota Highlander Base Plus with  in Naperville, IL
Photo 3: 2013 Toyota Highlander Base Plus in Naperville, IL
Photo 4: 2013 Toyota Highlander Base Plus in Naperville, IL
Photo 5: 2013 Toyota Highlander Base Plus in Naperville, IL

Automatic / AWD / 6 Cyl
17 mpg city / 22 mpg hwy

  • Call Dealer
  • Get Directions
$24,971

2013 Toyota Highlander Base Plus

34,362 miles / Naperville, IL

Photo 1: 2016 Toyota Highlander LE Plus with  in Chicago, IL
Photo 2: 2016 Toyota Highlander LE Plus with  in Chicago, IL
Photo 3: 2016 Toyota Highlander LE Plus with  in Chicago, IL

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

  • Call Dealer
  • Get Directions
$32,990

2016 Toyota Highlander LE Plus

5,868 miles / Chicago, IL

Photo 1: 2010 Toyota Highlander Limited with  in Naperville, IL

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

  • Dealer Page
  • Call
  • Get Directions
$16,977

2010 Toyota Highlander Limited

104,099 miles / Naperville, IL

Photo 1: Classic Silver Metallic 2013 Toyota Highlander Limited in Northbrook, IL exterior view from front driver's side
Photo 2: Classic Silver Metallic 2013 Toyota Highlander Limited in Northbrook, IL
Photo 3: cockpit view from driver’s seat 2013 Toyota Highlander Limited in Northbrook, IL
Photo 4: cockpit view from driver’s seat 2013 Toyota Highlander Limited in Northbrook, IL
Photo 5: Classic Silver Metallic 2013 Toyota Highlander Limited in Northbrook, IL front view of grill, headlights, hood and windshield

Automatic / AWD / 6 Cyl
17 mpg city / 22 mpg hwy

  • Call Dealer
  • Get Directions
$28,668

2013 Toyota Highlander Limited

36,849 miles / Northbrook, IL

Photo 1: Blizzard Pearl 2014 Toyota Highlander Limited in Bourbonnais, IL exterior view from front driver's side
Photo 2: Blizzard Pearl 2014 Toyota Highlander Limited in Bourbonnais, IL
Photo 3: cockpit view from driver’s seat 2014 Toyota Highlander Limited in Bourbonnais, IL
Photo 4: interior dashboard and console 2014 Toyota Highlander Limited in Bourbonnais, IL
Photo 5: Blizzard Pearl 2014 Toyota Highlander Limited in Bourbonnais, IL front view of grill, headlights, hood and windshield

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

  • Call Dealer
  • Get Directions
$30,700

2014 Toyota Highlander Limited

34,334 miles / Bourbonnais, IL

Photo 1:  2004 Toyota Highlander in Naperville, IL exterior view from front driver's side
Photo 2:  2004 Toyota Highlander in Naperville, IL
Photo 3: cockpit view from driver’s seat 2004 Toyota Highlander in Naperville, IL
Photo 4: interior dashboard and console 2004 Toyota Highlander in Naperville, IL
Photo 5:  2004 Toyota Highlander in Naperville, IL front view of grill, headlights, hood and windshield

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

  • Dealer Page
  • Call
  • Get Directions
$5,277

2004 Toyota Highlander

168,348 miles / Naperville, IL

Photo 1: 2005 Toyota Highlander Limited with  in Arlington Heights, IL
Photo 2: 2005 Toyota Highlander Limited with  in Arlington Heights, IL
Photo 3: 2005 Toyota Highlander Limited in Arlington Heights, IL
Photo 4: 2005 Toyota Highlander Limited in Arlington Heights, IL
Photo 5: 2005 Toyota Highlander Limited in Arlington Heights, IL

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

  • Call Dealer
  • Get Directions
$9,291

2005 Toyota Highlander Limited

110,795 miles / Arlington Heights, IL

Photo 1: Silver Sky Metallic 2015 Toyota Highlander XLE in Northbrook, IL exterior view from front driver's side
Photo 2: Silver Sky Metallic 2015 Toyota Highlander XLE in Northbrook, IL
Photo 3: cockpit view from driver’s seat 2015 Toyota Highlander XLE in Northbrook, IL
Photo 4: Silver Sky Metallic 2015 Toyota Highlander XLE in Northbrook, IL front view of grill, headlights, hood and windshield
Photo 5: Silver Sky Metallic 2015 Toyota Highlander XLE in Northbrook, IL exterior view from rear driver's side

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

  • Call Dealer
  • Get Directions
$32,444

2015 Toyota Highlander XLE

36,599 miles / Northbrook, IL

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

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

  • Call Dealer
  • Get Directions
$34,700

2015 Toyota Highlander Limited

19,869 miles / Bourbonnais, IL

Photo 1: 2008 Toyota Highlander Limited with  in Mundelein, IL
Photo 2: 2008 Toyota Highlander Limited with  in Mundelein, IL
Photo 3: 2008 Toyota Highlander Limited with  in Mundelein, IL
Photo 4: 2008 Toyota Highlander Limited with  in Mundelein, IL
Photo 5: 2008 Toyota Highlander Limited with  in Mundelein, IL

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

  • Call Dealer
  • Get Directions
$11,995

2008 Toyota Highlander Limited

137,963 miles / Mundelein, IL

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

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

  • Call Dealer
  • Get Directions
$28,994

2015 Toyota Highlander XLE

36,501 miles / Calumet City, IL

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

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

  • Call Dealer
  • Get Directions
$34,777

2015 Toyota Highlander Limited

46,107 miles / Naperville, IL

Photo 1: 2012 Toyota Highlander Base with  in Michigan City, IN
Photo 2: 2012 Toyota Highlander Base with  in Michigan City, IN
Photo 3: 2012 Toyota Highlander Base in Michigan City, IN
Photo 4: 2012 Toyota Highlander Base in Michigan City, IN
Photo 5: 2012 Toyota Highlander Base in Michigan City, IN

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

  • Call Dealer
  • Get Directions
$19,000

2012 Toyota Highlander Base

75,258 miles / Michigan City, IN

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

Automatic / AWD / 6 Cyl
17 mpg city / 22 mpg hwy

  • Call Dealer
  • Get Directions
$26,980

2013 Toyota Highlander Limited

31,513 miles / North Aurora, IL

Photo 1: Oasis Green Pearl 2006 Toyota Highlander in Downers Grove, IL exterior view from front driver's side
Photo 2: Oasis Green Pearl 2006 Toyota Highlander in Downers Grove, IL
Photo 3: interior dashboard and console 2006 Toyota Highlander in Downers Grove, IL
Photo 4: Oasis Green Pearl 2006 Toyota Highlander in Downers Grove, IL front view of grill, headlights, hood and windshield
Photo 5: Oasis Green Pearl 2006 Toyota Highlander in Downers Grove, IL exterior view of driver's side

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

  • Call Dealer
  • Get Directions
$8,000

2006 Toyota Highlander

102,149 miles / Downers Grove, IL

Photo 1: Millennium Silver Metallic 2004 Toyota Highlander Limited in Crystal Lake, IL exterior view from front driver's side
Photo 2: Millennium Silver Metallic 2004 Toyota Highlander Limited in Crystal Lake, IL
Photo 3: cockpit view from driver’s seat 2004 Toyota Highlander Limited in Crystal Lake, IL
Photo 4: interior dashboard and console 2004 Toyota Highlander Limited in Crystal Lake, IL
Photo 5: 2004 Toyota Highlander Limited with  in Crystal Lake, IL

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

  • Call Dealer
  • Get Directions
$6,733

2004 Toyota Highlander Limited

191,264 miles / Crystal Lake, IL

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

Automatic / AWD / 6 Cyl
17 mpg city / 22 mpg hwy

  • Call Dealer
  • Get Directions
$23,995

2013 Toyota Highlander SE

59,933 miles / Tinley Park, IL

Photo 1:  2014 Toyota Highlander XLE in Glendale Heights, IL exterior view from front driver's side
Photo 2:  2014 Toyota Highlander XLE in Glendale Heights, IL
Photo 3: cockpit view from driver’s seat 2014 Toyota Highlander XLE in Glendale Heights, IL
Photo 4: 2014 Toyota Highlander XLE with  in Glendale Heights, IL
Photo 5:  2014 Toyota Highlander XLE in Glendale Heights, IL front view of grill, headlights, hood and windshield

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

  • Call Dealer
  • Get Directions
$29,150

2014 Toyota Highlander XLE

31,751 miles / Glendale Heights, IL

Photo 1:  2013 Toyota Highlander Limited in Glenview, IL exterior view from front driver's side
Photo 2:  2013 Toyota Highlander Limited in Glenview, IL
Photo 3: cockpit view from driver’s seat 2013 Toyota Highlander Limited in Glenview, IL
Photo 4: interior dashboard and console 2013 Toyota Highlander Limited in Glenview, IL
Photo 5:  2013 Toyota Highlander Limited in Glenview, IL front view of grill, headlights, hood and windshield

Automatic / AWD / 6 Cyl
17 mpg city / 22 mpg hwy

  • Dealer Page
  • Call
  • Get Directions
$25,699

2013 Toyota Highlander Limited

55,046 miles / Glenview, IL

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

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

  • Call Dealer
  • Get Directions
$34,987

2014 Toyota Highlander Limited Platinum

37,265 miles / Crystal Lake, IL

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

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

  • Call Dealer
  • Get Directions
$26,922

2015 Toyota Highlander LE

33,074 miles / Elgin, IL