Used Porsche Cayman S for Sale in Chicago, IL
Buy a sporty Porsche Cayman S in the Windy City
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40 listings
- New Listing
- 45,140 miles
- 1 accident, 2 owners, personal use only
- 6cyl manual
- Porsche Barrington (31 mi away)
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Located in Barrington, IL / 31 miles away from Chicago, IL
Seal Gray Metallic 2006 Porsche Cayman S Recent Arrival! Bose, Sport Seats, Sport Shifter, Front fog lights, Garage door transmitter: HomeLink, Illumi...
AutoCheck Vehicle History Summary
Accident Free Vehicle: No
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
21 Combined MPG (18 City/26 Highway)
Listing Information:
VIN: WP0AB29866U781515
Stock: PPG3874
Certified Pre-Owned: No
Listed since: 12-17-2024 - 71,607 miles
- Odometer issue reported, 2 owners, personal use only
- 6cyl manual
- GR Auto Gallery of Grand Rapids (127 mi away)
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Located in Grand Rapids, MI / 127 miles away from Chicago, IL
Porsche knocked it out of the park with the debut of the Porsche Cayman which was a modified Boxster in a coupe version. Offering both the standard a...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Issue reported
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
21 Combined MPG (18 City/26 Highway)
Listing Information:
VIN: WP0AB29876U784617
Stock: B5762 L
Certified Pre-Owned: No
Listed since: 11-13-2024- 46,757 miles
- No accidents, 2 owners, personal use only
- 6cyl manual
- GR Auto Gallery of Grand Rapids (127 mi away)
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Located in Grand Rapids, MI / 127 miles away from Chicago, IL
Beneath its sleek exterior beats the heart of a true driver's car. The naturally aspirated 3.4 liter flat six channels its 295 horsepower to the rear ...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
21 Combined MPG (18 City/26 Highway)
Listing Information:
VIN: WP0AB29886U783220
Stock: P6265 L
Certified Pre-Owned: No
Listed since: 12-18-2024- 86,998 miles
- 1 accident, 6 owners, personal use only
- 6cyl manual
- The Auto Livery (237 mi away)
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Located in Fairfield, OH / 237 miles away from Chicago, IL
Super clean and extremely well optioned 987 Cayman S Coupe with the 3.4L Carrera derived flat 6cyl engine and all important 6spd manual transmission. ...
AutoCheck Vehicle History Summary
Accident Free Vehicle: No
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
21 Combined MPG (18 City/26 Highway)
Listing Information:
VIN: WP0AB29886U781631
Stock: 6U781631
Certified Pre-Owned: No
Listed since: 08-30-2024- $30,840fair price$1,596 above market
- 57,262 miles
- No accidents, 5 owners, personal use only
- 6cyl automatic
- Driving Xcellence (266 mi away)
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Located in Jeffersonville, IN / 266 miles away from Chicago, IL
- 60k MILES SERVICE ALREADY PERFORMED BY PORSCHE DEALER - 6-SPEED MANUAL - SPORT MODE BUTTON - SPORT CHRONO PACKAGE - SPEED ACTIVATED REAR SPOILER - P...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
21 Combined MPG (18 City/26 Highway)
Listing Information:
VIN: WP0AB29876U781703
Stock: 781703
Certified Pre-Owned: No
Listed since: 01-03-2024 - 43,637 miles
- 1 accident, 3 owners, personal use only
- 6cyl automatic
- Jeff's Motorcars (329 mi away)
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Located in North Canton, OH / 329 miles away from Chicago, IL
AutoCheck Vehicle History Summary
Accident Free Vehicle: No
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
21 Combined MPG (18 City/26 Highway)
Listing Information:
VIN: WP0AB29886U782648
Stock: 23627-P
Certified Pre-Owned: No
Listed since: 12-15-2024- $27,395fair price$1,533 below market
- 46,845 miles
- No accidents, 2 owners, personal use
- 6cyl automatic
- Inver Grove Toyota (343 mi away)
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Located in Inver Grove Heights, MN / 343 miles away from Chicago, IL
Carrera White 2006 Porsche Cayman S RWD 5-Speed Automatic with Tiptronic S 3.4L H6 SMPI DOHCOdometer is 22297 miles below market average! 20/28 City/H...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
21 Combined MPG (18 City/26 Highway)
Listing Information:
VIN: WP0AB29866U785712
Stock: A13304
Certified Pre-Owned: No
Listed since: 08-21-2024 - 19,266 miles
- No accidents, 3 owners, personal use only
- 6cyl automatic
- U Car Connect (355 mi away)
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Located in Eden Prairie, MN / 355 miles away from Chicago, IL
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
21 Combined MPG (18 City/26 Highway)
Listing Information:
VIN: WP0AB29886U781810
Stock: 17044
Certified Pre-Owned: No
Listed since: 10-25-2024- $23,472good price$2,631 below market
- 81,758 miles
- 1 accident, 6 owners, personal use only
- 6cyl automatic
- Moses Factory Outlet-Teays Valley (384 mi away)
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Located in Hurricane, WV / 384 miles away from Chicago, IL
20/28 City/Highway MPGMoses Auto Group utilizes MARKET VALUE PRICING on all the vehicles in our inventory. We use real-time market data to ensure that...
AutoCheck Vehicle History Summary
Accident Free Vehicle: No
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
21 Combined MPG (18 City/26 Highway)
Listing Information:
VIN: WP0AB29856U782333
Stock: OW24892
Certified Pre-Owned: No
Listed since: 12-09-2024 - 36,866 miles
- No accidents, 3 owners, personal use only
- 6cyl manual
- LW Automotive (405 mi away)
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Located in Pittsburgh, PA / 405 miles away from Chicago, IL
LW Automotive LW Automotive 9234 Perry Highway Pittsburgh, PA 15237 4**-3**-7*** FREE NATIONWIDE SHIPPING AT OUR ASKING PRICE! 2006 PORSCHE CAYMAN S F...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
21 Combined MPG (18 City/26 Highway)
Listing Information:
VIN: WP0AB29846U785899
Stock: 25714632
Certified Pre-Owned: No
Listed since: 09-12-2024- 51,559 miles
- No accidents, 4 owners, corporate fleet vehicle
- 6cyl manual
- LW Automotive (405 mi away)
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Located in Pittsburgh, PA / 405 miles away from Chicago, IL
LW Automotive LW Automotive 9234 Perry Highway Pittsburgh, PA 15237 4**-3**-7*** FREE NATIONWIDE SHIPPING AT OUR ASKING PRICE! 2006 PORSCHE CAYMAN S F...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: No
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
21 Combined MPG (18 City/26 Highway)
Listing Information:
VIN: WP0AB298X6U782215
Stock: 23321241
Certified Pre-Owned: No
Listed since: 08-25-2024- 72,221 miles
- Insurance loss reported, 12 owners, personal use
- 6cyl manual
- The Internet Car Lot (436 mi away)
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Located in Omaha, NE / 436 miles away from Chicago, IL
Please note that this vehicle has a branded title. Check out this very nice 2006 Porsche Cayman S! This vehicle looks and drives great! It has great o...
AutoCheck Vehicle History Summary
Accident Free Vehicle: No
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Issue reported
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
21 Combined MPG (18 City/26 Highway)
Listing Information:
VIN: WP0AB29876U780454
Stock: 780454COFA71801
Certified Pre-Owned: No- Price Drop$20,990great price$3,230 below market
- 93,907 miles
- 1 accident, 5 owners, personal use only
- 6cyl manual
- CarNation Motors (575 mi away)
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Located in Harrisburg, PA / 575 miles away from Chicago, IL
** ONLY 93K MILES ** ** VEHICLE COMES WITH 1 MONTH OR 1K MILES WHICHEVER COMES FIRST ON POWER TRAIN & TRANSMISSION, EXTENDED WARRANTIES ARE AVAILABLE ...
AutoCheck Vehicle History Summary
Accident Free Vehicle: No
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
21 Combined MPG (18 City/26 Highway)
Listing Information:
VIN: WP0AB29826U785111
Stock: 785111
Certified Pre-Owned: No
Listed since: 09-12-2024 - $29,495fair price$696 below market
- 55,373 miles
- No accidents, 5 owners, personal use only
- 6cyl manual
- FC Auto Sales & Service (587 mi away)
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Located in Falls Church, VA / 587 miles away from Chicago, IL
If you've been looking for just the right vehicle, then stop your search right here. Step into the 2006 Porsche Cayman S! Assembled with the most disc...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
21 Combined MPG (18 City/26 Highway)
Listing Information:
VIN: WP0AB29876U785668
Stock: 7983
Certified Pre-Owned: No
Listed since: 10-02-2024 - $27,990great price$4,222 below market
- 47,096 miles
- No accidents, 6 owners, personal use
- 6cyl automatic
- Autoleader (599 mi away)
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Located in Baltimore, MD / 599 miles away from Chicago, IL
2016 Porsche Cayman S in sleek black exterior with a matching black leather interior. This stunning sports coupe is the epitome of Porsche s precision...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
21 Combined MPG (18 City/26 Highway)
Listing Information:
VIN: WP0AB29826U781155
Stock: 1155
Certified Pre-Owned: No
Listed since: 09-19-2024 - $28,590good price$2,585 below market
- 48,307 miles
- No accidents, 2 owners, personal use only
- 6cyl manual
- Belmonte Auto Imports (639 mi away)
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Located in Raleigh, NC / 639 miles away from Chicago, IL
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
21 Combined MPG (18 City/26 Highway)
Listing Information:
VIN: WP0AB298X6U783476
Stock: R1013439
Certified Pre-Owned: No
Listed since: 10-24-2024 - $28,500fair price$244 below market
- 64,000 miles
- 1 accident, 4 owners, corporate fleet vehicle
- 6cyl manual
- Holiday Motors Portsmouth (697 mi away)
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Located in Portsmouth, VA / 697 miles away from Chicago, IL
PLEASE MAKE AN APPOINTMENT TO ENSURE AVAILABILITY. Gargage kept and in amazing condition in every way. This Cayman S is incredibly fun to drive and es...
AutoCheck Vehicle History Summary
Accident Free Vehicle: No
Personal Use Only: No
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
21 Combined MPG (18 City/26 Highway)
Listing Information:
VIN: WP0AB29836U782203
Stock: 82203
Certified Pre-Owned: No
Listed since: 11-14-2024 - Price Drop$27,144good price$2,576 below market
- 58,413 miles
- No accidents, 2 owners, personal use only
- 6cyl manual
- Blasius Preowned Auto Sales (751 mi away)
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Located in Waterbury, CT / 751 miles away from Chicago, IL
2006 Porsche Cayman S Atlas Gray Metallic BACKUP CAMERA, HEATED LEATHER SEATS, NO ACCIDENTS, ALLOY WHEELS, BLIND SPOT MONITOR, Cayman S, 2D Coupe, 3.4...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
21 Combined MPG (18 City/26 Highway)
Listing Information:
VIN: WP0AB29896U785185
Stock: U8815A
Certified Pre-Owned: No
Listed since: 01-03-2025 - $29,995good price$2,296 below market
- 41,104 miles
- 1 accident, 4 owners, personal use only
- 6cyl manual
- Coventry Motorcar (784 mi away)
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Located in Coventry, CT / 784 miles away from Chicago, IL
FULLY SERVICED INCLUDING ALL MANUALS AND 2-KEYS. PLEASE INQUIRE FOR MORE DETAILS. Visit www.COVENTRYMOTORCAR.com for more photos of this vehicle.
AutoCheck Vehicle History Summary
Accident Free Vehicle: No
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
21 Combined MPG (18 City/26 Highway)
Listing Information:
VIN: WP0AB29856U784616
Stock: 784616
Certified Pre-Owned: No
Listed since: 01-04-2025 - $33,995fair price
- 49,036 miles
- No accidents, 5 owners, personal use only
- 6cyl manual
- Auto Park Dallas (798 mi away)
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Located in Lewisville, TX / 798 miles away from Chicago, IL
AutoPark Dallas is thrilled to offer you this Beautiful LOW MILEAGE 2006 Porsche Cayman S for sale! The classic Porsche styling, sublime steering, and...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
21 Combined MPG (18 City/26 Highway)
Listing Information:
VIN: WP0AB29866U780722
Stock: 2289
Certified Pre-Owned: No
Listed since: 09-23-2024 - $26,995fair price
- 84,829 miles
- No accidents, 5 owners, corporate fleet vehicle
- 6cyl manual
- Auto Park Dallas (798 mi away)
Close
Located in Lewisville, TX / 798 miles away from Chicago, IL
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: No
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
21 Combined MPG (18 City/26 Highway)
Listing Information:
VIN: WP0AB29816U780630
Stock: 2319-TR2
Certified Pre-Owned: No
Listed since: 09-29-2024
Showing 1 - 21 out of 40 listings
Consumer Reviews for the Porsche Cayman S
Read recent reviews for the Porsche Cayman S
Luv This Red Cayman S
JHudson, 07/14/2022
2006 Porsche Cayman S
I bought my 2006 Cayman S about three years ago or more. I had a MR2 that continuously had engine related problems. Got totaled by a rear ender. I looked around and the ad came about from no where. I went to see the vehicle, drove it, and the rest is pleasant history. A few days after having the car, it would not start. Got a new battery, no more problems related to starting. A few … weeks later the water pump started leaking. I was glad to know it only needed a water pump and not an engine. I replaced the rear trunk brake light. Since then the car has run as beautifully as it looks .It is a head turner though I try and maintain a sense of humility at the gas pump when people want to discuss it. I think the problems with the battery and water pump has to do with the car not being driven enough. It seems many people buy this car and let them sit to the side to save mileage or value on return. I think I got this car at just the right age to drive it responsibly. I agree with the other positive comments I have read.
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