• S
  • GT4
  • GTS
  • Base
  • R
  • 2014
  • Manual
  • Black
  • Great Deal
  • 2016
  • One Owner
  • Low Mileage
  • Rain-Sensing Wipers
  • Well-Equipped
  • Rare Model
  • 2015
  • Red
  • 2008
  • 2012
  • Premium Package
  • 2006
  • Silver
  • Good Deal
  • 2009
  • 2011
  • White
  • Fair Price
  • Lower Than Average Mileage
  • Certified Pre-Owned
  • Popular Model
  • 2010
  • Low Fuel Costs
  • 2007

Price Range

$0 $60,000+

Max Mileage

New $80,000+

MPG

Min 14 Max 50

MORE

76 Results for

Used Porsche Cayman For Sale in Chicago, IL

Search Results

Photo 1: Lapis Blue Metallic 2006 Porsche Cayman S in Chicago, IL exterior view from front driver's side
Photo 2: Lapis Blue Metallic 2006 Porsche Cayman S in Chicago, IL
Photo 3: interior dashboard and console 2006 Porsche Cayman S in Chicago, IL
Photo 4: cockpit view from driver’s seat 2006 Porsche Cayman S in Chicago, IL
Photo 5: 2006 Porsche Cayman S in Chicago, IL

Manual / RWD / 6 Cyl
18 mpg city / 26 mpg hwy

  • Get Directions
$31,995

2006 Porsche Cayman S

16,001 miles Chicago, IL

Photo 1: Carmine Red 2016 Porsche Cayman GT4 in Highland Park, IL exterior view from front driver's side
Photo 2: Carmine Red 2016 Porsche Cayman GT4 in Highland Park, IL
Photo 3: interior dashboard and console 2016 Porsche Cayman GT4 in Highland Park, IL
Photo 4: 2016 Porsche Cayman GT4 with  in Highland Park, IL
Photo 5: Carmine Red 2016 Porsche Cayman GT4 in Highland Park, IL front view of grill, headlights, hood and windshield

Manual / RWD / 6 Cyl
18 mpg city / 23 mpg hwy

  • Get Directions
$111,995

2016 Porsche Cayman GT4

3,360 miles Highland Park, IL

Photo 1:  2016 Porsche Cayman GT4 in Barrington, IL exterior view from front driver's side
Photo 2:  2016 Porsche Cayman GT4 in Barrington, IL
Photo 3: interior dashboard and console 2016 Porsche Cayman GT4 in Barrington, IL
Photo 4: 2016 Porsche Cayman GT4 with  in Barrington, IL
Photo 5:  2016 Porsche Cayman GT4 in Barrington, IL front view of grill, headlights, hood and windshield

Manual / RWD / 6 Cyl
18 mpg city / 23 mpg hwy

  • Get Directions
$107,000

2016 Porsche Cayman GT4

9,131 miles Barrington, IL

Photo 1: Carmon Red Metallic 2006 Porsche Cayman S in Highland Park, IL exterior view from front driver's side
Photo 2: Carmon Red Metallic 2006 Porsche Cayman S in Highland Park, IL
Photo 3: cockpit view from driver’s seat 2006 Porsche Cayman S in Highland Park, IL
Photo 4: 2006 Porsche Cayman S in Highland Park, IL
Photo 5: Carmon Red Metallic 2006 Porsche Cayman S in Highland Park, IL front view of grill, headlights, hood and windshield

Manual / RWD / 6 Cyl
18 mpg city / 26 mpg hwy

  • Get Directions
$25,995

2006 Porsche Cayman S

41,159 miles Highland Park, IL

Photo 1: Carmine Red 2016 Porsche Cayman GT4 in Westmont, IL exterior view from front driver's side
Photo 2: Carmine Red 2016 Porsche Cayman GT4 in Westmont, IL
Photo 3: interior dashboard and console 2016 Porsche Cayman GT4 in Westmont, IL
Photo 4: 2016 Porsche Cayman GT4 with  in Westmont, IL
Photo 5: Carmine Red 2016 Porsche Cayman GT4 in Westmont, IL front view of grill, headlights, hood and windshield

Manual / RWD / 6 Cyl
18 mpg city / 23 mpg hwy

  • Get Directions
$108,890

2016 Porsche Cayman GT4

3,524 miles Westmont, IL

Photo 1: Carrara White Metallic 2016 Porsche Cayman GT4 in Bensenville, IL
Photo 2: interior dashboard and console 2016 Porsche Cayman GT4 in Bensenville, IL
Photo 3: cockpit view from driver’s seat 2016 Porsche Cayman GT4 in Bensenville, IL
Photo 4: 2016 Porsche Cayman GT4 with  in Bensenville, IL
Photo 5: Carrara White Metallic 2016 Porsche Cayman GT4 in Bensenville, IL front view of grill, headlights, hood and windshield

Manual / RWD / 6 Cyl
18 mpg city / 23 mpg hwy

  • Get Directions
$98,998

2016 Porsche Cayman GT4

3,720 miles Bensenville, IL

Photo 1: Jet Black Metallic 2016 Porsche Cayman GT4 in Highland Park, IL exterior view from front driver's side
Photo 2: Jet Black Metallic 2016 Porsche Cayman GT4 in Highland Park, IL
Photo 3: interior dashboard and console 2016 Porsche Cayman GT4 in Highland Park, IL
Photo 4: cockpit view from driver’s seat 2016 Porsche Cayman GT4 in Highland Park, IL
Photo 5: 2016 Porsche Cayman GT4 with  in Highland Park, IL

Manual / RWD / 6 Cyl
18 mpg city / 23 mpg hwy

  • Get Directions
$112,995

2016 Porsche Cayman GT4

7,302 miles Highland Park, IL

Photo 1: Jet Black Metallic 2015 Porsche Cayman in Orland Park, IL

Manual / RWD / 6 Cyl
20 mpg city / 29 mpg hwy

  • Get Directions
$45,000

2015 Porsche Cayman

30,599 miles Orland Park, IL

Photo 1: Carrara White Metallic 2016 Porsche Cayman GT4 in Westmont, IL exterior view from front driver's side
Photo 2: Carrara White Metallic 2016 Porsche Cayman GT4 in Westmont, IL
Photo 3: interior dashboard and console 2016 Porsche Cayman GT4 in Westmont, IL
Photo 4: 2016 Porsche Cayman GT4 with  in Westmont, IL
Photo 5: Carrara White Metallic 2016 Porsche Cayman GT4 in Westmont, IL front view of grill, headlights, hood and windshield

Manual / RWD / 6 Cyl
18 mpg city / 23 mpg hwy

  • Get Directions
$99,980

2016 Porsche Cayman GT4

6,212 miles Westmont, IL

Photo 1:  2016 Porsche Cayman GT4 in Barrington, IL exterior view from front driver's side
Photo 2:  2016 Porsche Cayman GT4 in Barrington, IL
Photo 3: cockpit view from driver’s seat 2016 Porsche Cayman GT4 in Barrington, IL
Photo 4:  2016 Porsche Cayman GT4 in Barrington, IL front view of grill, headlights, hood and windshield
Photo 5: 2016 Porsche Cayman GT4 with  in Barrington, IL

Manual / RWD / 6 Cyl
18 mpg city / 23 mpg hwy

  • Get Directions
$96,900

2016 Porsche Cayman GT4

8,147 miles Barrington, IL

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

Manual / RWD / 6 Cyl
20 mpg city / 27 mpg hwy

  • Get Directions
$51,915

2014 Porsche Cayman S

6,303 miles Glendale Heights, IL

Photo 1:  2015 Porsche Cayman S in Westmont, IL exterior view from front driver's side
Photo 2: interior dashboard and console 2015 Porsche Cayman S in Westmont, IL
Photo 3: cockpit view from driver’s seat 2015 Porsche Cayman S in Westmont, IL
Photo 4: 2015 Porsche Cayman S in Westmont, IL
Photo 5:  2015 Porsche Cayman S in Westmont, IL front view of grill, headlights, hood and windshield

Automatic / RWD / 6 Cyl
21 mpg city / 29 mpg hwy

  • Get Directions
$51,800

2015 Porsche Cayman S

36,988 miles Westmont, IL

Photo 1: Agate Gray Metallic 2014 Porsche Cayman in Westmont, IL exterior view from front driver's side
Photo 2: Agate Gray Metallic 2014 Porsche Cayman in Westmont, IL
Photo 3: interior dashboard and console 2014 Porsche Cayman in Westmont, IL
Photo 4: 2014 Porsche Cayman with  in Westmont, IL
Photo 5: Agate Gray Metallic 2014 Porsche Cayman in Westmont, IL front view of grill, headlights, hood and windshield

Manual / RWD / 6 Cyl
20 mpg city / 29 mpg hwy

  • Get Directions
$44,000

2014 Porsche Cayman

25,595 miles Westmont, IL

Photo 1: Aqua Blue Metallic 2012 Porsche Cayman in Chicago, IL exterior view from front driver's side
Photo 2: Aqua Blue Metallic 2012 Porsche Cayman in Chicago, IL
Photo 3: interior dashboard and console 2012 Porsche Cayman in Chicago, IL
Photo 4: cockpit view from driver’s seat 2012 Porsche Cayman in Chicago, IL
Photo 5: 2012 Porsche Cayman with  in Chicago, IL

Automatic / RWD / 6 Cyl
20 mpg city / 29 mpg hwy

  • Get Directions
$39,995

2012 Porsche Cayman

23,701 miles Chicago, IL

Photo 1: Dark Blue Metallic 2015 Porsche Cayman in Orland Park, IL
Photo 2: interior dashboard and console 2015 Porsche Cayman in Orland Park, IL
Photo 3: cockpit view from driver’s seat 2015 Porsche Cayman in Orland Park, IL
Photo 4: 2015 Porsche Cayman in Orland Park, IL
Photo 5: Dark Blue Metallic 2015 Porsche Cayman in Orland Park, IL front view of grill, headlights, hood and windshield

Manual / RWD / 6 Cyl
20 mpg city / 29 mpg hwy

  • Get Directions
$47,000

2015 Porsche Cayman

17,786 miles Orland Park, IL

Photo 1:  2016 Porsche Cayman GT4 in Evanston, IL exterior view from front driver's side
Photo 2:  2016 Porsche Cayman GT4 in Evanston, IL
Photo 3: interior dashboard and console 2016 Porsche Cayman GT4 in Evanston, IL
Photo 4:  2016 Porsche Cayman GT4 in Evanston, IL front view of grill, headlights, hood and windshield
Photo 5: 2016 Porsche Cayman GT4 with  in Evanston, IL

Manual / RWD / 6 Cyl
18 mpg city / 23 mpg hwy

  • Get Directions
$98,994

2016 Porsche Cayman GT4

16,501 miles Evanston, IL

Photo 1: Dark Blue Metallic 2011 Porsche Cayman in Orland Park, IL exterior view from front driver's side
Photo 2: Dark Blue Metallic 2011 Porsche Cayman in Orland Park, IL
Photo 3: interior dashboard and console 2011 Porsche Cayman in Orland Park, IL
Photo 4: 2011 Porsche Cayman with  in Orland Park, IL
Photo 5: 2011 Porsche Cayman in Orland Park, IL

Manual / RWD / 6 Cyl
19 mpg city / 26 mpg hwy

  • Get Directions
$33,000

2011 Porsche Cayman

25,518 miles Orland Park, IL

Photo 1: Sapphire Blue Metallic 2016 Porsche Cayman in Westmont, IL exterior view from front driver's side
Photo 2: interior dashboard and console 2016 Porsche Cayman in Westmont, IL
Photo 3: cockpit view from driver’s seat 2016 Porsche Cayman in Westmont, IL
Photo 4: 2016 Porsche Cayman in Westmont, IL
Photo 5: Sapphire Blue Metallic 2016 Porsche Cayman in Westmont, IL front view of grill, headlights, hood and windshield

Automatic / RWD / 6 Cyl
22 mpg city / 31 mpg hwy

  • Get Directions
$52,800

2016 Porsche Cayman

9,838 miles Westmont, IL

Photo 1: Midnight Blue Metallic 2008 Porsche Cayman S in Westmont, IL exterior view from front driver's side
Photo 2: interior dashboard and console 2008 Porsche Cayman S in Westmont, IL
Photo 3: cockpit view from driver’s seat 2008 Porsche Cayman S in Westmont, IL
Photo 4: 2008 Porsche Cayman S in Westmont, IL
Photo 5: Midnight Blue Metallic 2008 Porsche Cayman S in Westmont, IL front view of grill, headlights, hood and windshield

Automatic / RWD / 6 Cyl
18 mpg city / 25 mpg hwy

  • Get Directions
$28,800

2008 Porsche Cayman S

52,212 miles Westmont, IL

Photo 1: Guards Red 2016 Porsche Cayman GT4 in Warrenville, IL exterior view from front driver's side
Photo 2: interior dashboard and console 2016 Porsche Cayman GT4 in Warrenville, IL
Photo 3: cockpit view from driver’s seat 2016 Porsche Cayman GT4 in Warrenville, IL
Photo 4: 2016 Porsche Cayman GT4 with  in Warrenville, IL
Photo 5: Guards Red 2016 Porsche Cayman GT4 in Warrenville, IL front view of grill, headlights, hood and windshield

Manual / RWD / 6 Cyl
18 mpg city / 23 mpg hwy

  • Get Directions
$119,800

2016 Porsche Cayman GT4

5,407 miles Warrenville, IL

Photo 1:  2008 Porsche Cayman S in Downers Grove, IL exterior view from front driver's side
Photo 2:  2008 Porsche Cayman S in Downers Grove, IL
Photo 3: interior dashboard and console 2008 Porsche Cayman S in Downers Grove, IL
Photo 4: cockpit view from driver’s seat 2008 Porsche Cayman S in Downers Grove, IL
Photo 5:  2008 Porsche Cayman S in Downers Grove, IL front view of grill, headlights, hood and windshield

Manual / RWD / 6 Cyl
18 mpg city / 26 mpg hwy

  • Get Directions
$29,985

2008 Porsche Cayman S

49,949 miles Downers Grove, IL

Photo 1:  2014 Porsche Cayman S in Warrenville, IL exterior view from front driver's side
Photo 2: interior dashboard and console 2014 Porsche Cayman S in Warrenville, IL
Photo 3: cockpit view from driver’s seat 2014 Porsche Cayman S in Warrenville, IL
Photo 4: 2014 Porsche Cayman S in Warrenville, IL
Photo 5:  2014 Porsche Cayman S in Warrenville, IL front view of grill, headlights, hood and windshield

Automatic / RWD / 6 Cyl
21 mpg city / 29 mpg hwy

  • Get Directions
$47,800

2014 Porsche Cayman S

43,336 miles Warrenville, IL

Photo 1:  2012 Porsche Cayman R in Warrenville, IL exterior view from front driver's side
Photo 2: interior dashboard and console 2012 Porsche Cayman R in Warrenville, IL
Photo 3: cockpit view from driver’s seat 2012 Porsche Cayman R in Warrenville, IL
Photo 4: 2012 Porsche Cayman R with  in Warrenville, IL
Photo 5:  2012 Porsche Cayman R in Warrenville, IL front view of grill, headlights, hood and windshield

Manual / RWD / 6 Cyl
19 mpg city / 26 mpg hwy

  • Get Directions
$65,800

2012 Porsche Cayman R

14,955 miles Warrenville, IL

Photo 1: Platinum Silver Metallic 2011 Porsche Cayman in Buffalo Grove, IL
Photo 2: interior dashboard and console 2011 Porsche Cayman in Buffalo Grove, IL
Photo 3: cockpit view from driver’s seat 2011 Porsche Cayman in Buffalo Grove, IL
Photo 4: 2011 Porsche Cayman with  in Buffalo Grove, IL
Photo 5: Platinum Silver Metallic 2011 Porsche Cayman in Buffalo Grove, IL front view of grill, headlights, hood and windshield

Manual / RWD / 6 Cyl
19 mpg city / 26 mpg hwy

  • Get Directions
$25,975

2011 Porsche Cayman

63,860 miles Buffalo Grove, IL