Used Porsche Cayman for Sale in Chicago, IL
Buy a luxurious Porsche Cayman in the Windy City
Skip to FiltersReport abuse
32 listings
- $34,990great price$5,658 below market
- 69,401 miles
- No accidents, 3 owners, personal use only
- 6cyl automated manual
- Carvana - Chicago (41 mi away)
- Home delivery*
Close
Located in Chicago, IL / 41 miles away from Chicago, IL
At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts you ...
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:
24 Combined MPG (20 City/30 Highway)
Listing Information:
VIN: WP0AA2A8XFK160207
Stock: 2003519478
Certified Pre-Owned: No
Listed since: 03-20-2025 - $108,995good price$8,734 below market
- 11,623 miles
- No accidents, 4 owners, personal use only
- 6cyl manual
- Motor Cars of Chicago (34 mi away)
Close
Located in Joliet, IL / 34 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:
Listing Information:
VIN: WP0AC2A89GK191850
Stock: 5565
Certified Pre-Owned: No - $49,888fair price$407 above market
- 38,776 miles
- No accidents, 3 owners, personal use only
- 6cyl automated manual
- Chicago Auto Place (22 mi away)
Close
Located in Downers Grove, IL / 22 miles away from Chicago, IL
Thank you for visiting another one of Chicago Auto Place's exclusive listings! CALL US NOW FOR A FREE QUOTE 630-422-1122 FOR MORE PHOTOS VISIT WWW.CHI...
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:
23 Combined MPG (20 City/28 Highway)
Listing Information:
VIN: WP0AB2A8XEK193199
Stock: H8960
Certified Pre-Owned: No
Listed since: 01-03-2025 - $49,995fair price$882 above market
- 35,859 miles
- 1 accident, 2 owners, personal use only
- 6cyl automated manual
- Unlimited Motors Elwood (146 mi away)
Close
Located in Elwood, IN / 146 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:
23 Combined MPG (20 City/28 Highway)
Listing Information:
VIN: WP0AB2A8XEK191405
Stock: STK191405
Certified Pre-Owned: No
Listed since: 04-11-2025 - $119,995
- 34,195 miles
- No accidents, 2 owners, personal use
- 6cyl manual
- Reina International Auto (86 mi away)
Close
Located in Brookfield, WI / 86 miles away from Chicago, IL
2016 Porsche Cayman GT4, Carrera White Metallic on Black, Clean Carfax, 2 Owner, Only 34K Miles, 6-Speed Manual, modified with enlarged plenum 82 mm a...
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:
Listing Information:
VIN: WP0AC2A83GK192587
Stock: 2587C
Certified Pre-Owned: No
Listed since: 10-03-2024 - 47,604 miles
- No accidents, 3 owners, personal use only
- 6cyl automatic
- Carmel Motors (161 mi away)
Close
Located in Indianapolis, IN / 161 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: WP0AB29888U781678
Stock: F781678
Certified Pre-Owned: No
Listed since: 10-30-2024- Price Drop$68,590
- 37,283 miles
- No accidents, 5 owners, personal use only
- 6cyl automated manual
- Carvana - Indianapolis (164 mi away)
- Home delivery*
Close
Located in Indianapolis, IN / 164 miles away from Chicago, IL
At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts you ...
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:
22 Combined MPG (19 City/27 Highway)
Listing Information:
VIN: WP0AB2A82CS793311
Stock: 2003581206
Certified Pre-Owned: No
Listed since: 04-01-2025 - Price Drop$43,990great price$5,861 below market
- 19,931 miles
- No accidents, 3 owners, personal use
- 6cyl automated manual
- Carvana (In-stock online)
- Home delivery*
Close
Located in Birmingham, AL / 580 miles away from Chicago, IL
At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts you ...
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:
24 Combined MPG (20 City/30 Highway)
Listing Information:
VIN: WP0AA2A82FK162310
Stock: 2003604613
Certified Pre-Owned: No
Listed since: 03-25-2025 - $49,800great price$6,677 below market
- 11,887 miles
- No accidents, 3 owners, personal use only
- 6cyl automated manual
- Chicago Motor Cars (30 mi away)
Close
Located in West Chicago, IL / 30 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:
24 Combined MPG (20 City/30 Highway)
Listing Information:
VIN: WP0AA2A85GK171391
Stock: 21580A
Certified Pre-Owned: No
Listed since: 03-13-2025 - Price Drop$102,727good price$13,984 below market
- 9,007 miles
- No accidents, 1 owner, personal use only
- 6cyl manual
- Kunes Chevrolet GMC (70 mi away)
Close
Located in Elkhorn, WI / 70 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:
Listing Information:
VIN: WP0AC2A84GK197779
Stock: 06P2044
Certified Pre-Owned: No
Listed since: 02-28-2025 - $69,987great price$6,497 below market
- 42,113 miles
- No accidents, 5 owners, personal use
- 6cyl automated manual
- Dreyer & Reinbold Subaru (177 mi away)
Close
Located in Greenwood, IN / 177 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:
22 Combined MPG (19 City/26 Highway)
Listing Information:
VIN: WP0AB2A89FK182924
Stock: A11265A
Certified Pre-Owned: No
Listed since: 03-16-2025 - $60,900good price$4,057 below market
- 4,885 miles
- No accidents, 1 owner, personal use only
- 6cyl automated manual
- Midwest Highline (74 mi away)
Close
Located in Rockford, IL / 74 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:
23 Combined MPG (20 City/28 Highway)
Listing Information:
VIN: WP0AB2A87FK182601
Stock: 24693
Certified Pre-Owned: No
Listed since: 06-07-2024 - $29,154good price$3,815 below market
- 67,139 miles
- No accidents, 3 owners, personal use only
- 6cyl automatic
- Tom Wood Porsche (157 mi away)
Close
Located in Indianapolis, IN / 157 miles away from Chicago, IL
2007 Porsche Cayman S ?" High-Performance Sports CoupeExperience the thrill of driving with the 2007 Porsche Cayman S, a precision-engineered sports c...
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: WP0AB29857U781166
Stock: UP22214
Certified Pre-Owned: No
Listed since: 04-02-2025 - $40,990great price$5,587 below market
- 54,060 miles
- 1 accident, 4 owners, personal use only
- 6cyl automated manual
- Carvana (In-stock online)
- Home delivery*
Close
Located in Sacramento, CA / 1,788 miles away from Chicago, IL
At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts you ...
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:
23 Combined MPG (20 City/28 Highway)
Listing Information:
VIN: WP0AB2A81EK192524
Stock: 2003317039
Certified Pre-Owned: No
Listed since: 12-03-2024 - $35,995fair price$2,992 below market
- 19,198 miles
- No accidents, 1 owner, personal use only
- 6cyl automatic
- Greater Chicago Motors (23 mi away)
Close
Located in Glendale Heights, IL / 23 miles away from Chicago, IL
2007 Cayman S Yes Real Miles!!! Carfax Certified~ No Accidents BRAND NEW tires!! BRAND NEW alcantara upgraded headliner 1 Owner Garage Queen Very Rare...
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: WP0AB29817U781097
Stock: GCM7261
Certified Pre-Owned: No
Listed since: 02-18-2025 - Price Drop$40,725good price$4,379 below market
- 56,913 miles
- 1 accident, 7 owners, personal use only
- 6cyl automated manual
- Motor Werks Honda (31 mi away)
Close
Located in Barrington, IL / 31 miles away from Chicago, IL
Unleash thrilling performance and timeless design with the **Rhodium Silver Metallic 2014 Porsche Cayman S RWD**, a sports car engineered for precisio...
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:
23 Combined MPG (20 City/28 Highway)
Listing Information:
VIN: WP0AB2A82EK193357
Stock: PHR2726
Certified Pre-Owned: No
Listed since: 10-17-2024 - $49,900fair price$1,555 below market
- 26,317 miles
- No accidents, 2 owners, personal use only
- 6cyl automated manual
- GR Auto Gallery of Grand Rapids (126 mi away)
Close
Located in Grand Rapids, MI / 126 miles away from Chicago, IL
GR Auto Gallery is pleased to offer this high quality, low mile, fully documented 2014 Porsche Cayman S to the world market. The car is presented in 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:
23 Combined MPG (20 City/28 Highway)
Listing Information:
VIN: WP0AB2A80EK191476
Stock: P6281 L
Certified Pre-Owned: No
Listed since: 01-07-2025 - New Listing$111,900fair price$1,337 below market
- 9,435 miles
- No accidents, 4 owners, personal use only
- 6cyl manual
- Porsche Barrington (31 mi away)
Close
Located in Barrington, IL / 31 miles away from Chicago, IL
Silver 2016 Porsche Cayman GT4 Recent Arrival! 3.8L H6 DOHC GT4981810 Cayman GT458 Leather Interior in Black with Alcantara, Stitching in Yellow $1,09...
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:
Listing Information:
VIN: WP0AC2A87GK191958
Stock: PPG3963
Certified Pre-Owned: No
Listed since: 04-09-2025 - $50,999fair price$858 below market
- 24,888 miles
- No accidents, 3 owners, personal use only
- 6cyl automated manual
- Specialty Motors (37 mi away)
Close
Located in Gurnee, IL / 37 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:
23 Combined MPG (20 City/28 Highway)
Listing Information:
VIN: WP0AB2A84EK191013
Stock: 191013
Certified Pre-Owned: No
Listed since: 04-16-2025 - New Listing$53,590fair price$906 below market
- 29,131 miles
- No accidents, 4 owners, personal use
- 6cyl manual
- Carvana (In-stock online)
- Home delivery*
Close
Located in Atlanta, GA / 586 miles away from Chicago, IL
At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts you ...
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:
23 Combined MPG (20 City/28 Highway)
Listing Information:
VIN: WP0AB2A84FK183656
Stock: 2003636700
Certified Pre-Owned: No
Listed since: 04-09-2025 - New Listing$49,998fair price$1,699 above market
- 23,297 miles
- 6cyl manual
- CarMax (In-stock online)
- Transfer available from NV to IL*
Close
Located in Las Vegas, NV / 1,527 miles away from Chicago, IL
CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...
AutoCheck Vehicle History Summary Unavailable.
Features and Specs:
24 Combined MPG (20 City/30 Highway)
Listing Information:
VIN: WP0AA2A80GK171735
Stock: 26742001
Certified Pre-Owned: No
Showing 1 - 21 out of 32 listings
Consumer Reviews for the Porsche Cayman
Read recent reviews for the Porsche Cayman
Excellent on the race course
NW Driver, 11/10/2020
2016 Porsche Cayman
Took my 2016 Cayman S pdk to the race track for a high performance driving course and then last week for lapping. The other reviewers are right in the mark- at 45k miles the car is a great daily driver and a true sports car.
The brakes stop quickly and predictably, and the car is stable at 128mph; and it takes the S turns remarkably well.
My only regrets- not finding one with the sports … exhaust, nav and the Chrono package. But the price was right and the car looks brand new- given the build quality.
Filters
Skip to ResultsApplied Filters4Active
Make & Model
Year
New / Used
Price & Payments
Price Rating
Trim
Mileage
Accidents & History
Engine & Drivetrain
Exterior Color
Interior Color
Total Seating
Edmunds Review
Features
Options & Packages
MPG
* Delivery of any kind does not apply to Alaska and Hawaii. Contact the dealer for delivery details, restrictions and costs.