Used Porsche Cayman for Sale in Chicago, IL
Buy a luxurious Porsche Cayman in the Windy City
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26 listings
- $27,999great price$5,841 below market
- 56,077 miles
- No accidents, 2 owners, personal use only
- 6cyl automatic
- Specialty Motors (37 mi away)
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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:
21 Combined MPG (18 City/26 Highway)
Listing Information:
VIN: WP0AB29827U783232
Stock: 783232
Certified Pre-Owned: No - New Listing$56,990great price$9,405 below market
- 8,083 miles
- No accidents, 2 owners, corporate fleet vehicle
- 6cyl automated manual
- Carvana - Indianapolis (164 mi away)
- Home delivery*
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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: 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:
23 Combined MPG (20 City/28 Highway)
Listing Information:
VIN: WP0AB2A89FK184415
Stock: 2003837617
Certified Pre-Owned: No
Listed since: 06-21-2025 - $67,000good price$6,844 below market
- 42,114 miles
- No accidents, 5 owners, personal use
- 6cyl automated manual
- AutoGiant USA (161 mi away)
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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:
22 Combined MPG (19 City/26 Highway)
Listing Information:
VIN: WP0AB2A89FK182924
Stock: F182924
Certified Pre-Owned: No
Listed since: 05-09-2025 - $27,999good price$1,937 below market
- 55,014 miles
- No accidents, 4 owners, personal use only
- 6cyl manual
- Specialty Motors (37 mi away)
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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/29 Highway)
Listing Information:
VIN: WP0AA29897U762137
Stock: 762137
Certified Pre-Owned: No - $24,999fair price$969 below market
- 53,413 miles
- No accidents, 6 owners, corporate fleet vehicle
- 6cyl automatic
- Specialty Motors (37 mi away)
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Located in Gurnee, IL / 37 miles away from Chicago, IL
** VEHICLE LOCATION MAY VARY BETWEEN OUR TWO DEALERSHIPS, PLEASE CALL AHEAD TO CONFIRM LOCATION BEFORE VISITING *** 2008 PORSCHE CAYMAN COUPE 2D ** BL...
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:
23 Combined MPG (20 City/29 Highway)
Listing Information:
VIN: WP0AA29888U762714
Stock: 762714
Certified Pre-Owned: No - $109,995fair price$2,533 above market
- 34,195 miles
- No accidents, 2 owners, personal use
- 6cyl manual
- Reina International Auto (86 mi away)
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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 - 56,897 miles
- No accidents, 2 owners, personal use
- 6cyl 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:
24 Combined MPG (20 City/30 Highway)
Listing Information:
VIN: WP0AA2A88GK171515
Stock: 171515
Certified Pre-Owned: No- New Listing$51,998great price$4,607 below market
- 18,260 miles
- 1 accident, 3 owners, personal use only
- 6cyl manual
- CarMax (In-stock online)
- Transfer available from WA to IL*
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Located in Vancouver, WA / 1,747 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
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: WP0AB2A82EK190801
Stock: 27291577
Certified Pre-Owned: No - $38,590great price$4,231 below market
- 52,759 miles
- No accidents, 4 owners, personal use
- 6cyl automated manual
- Carvana (In-stock online)
- Home delivery*
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Located in Phoenix, AZ / 1,447 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: WP0AA2A86EK170120
Stock: 2003806690
Certified Pre-Owned: No
Listed since: 06-25-2025 - New Listing$47,998good price$4,195 below market
- 29,794 miles
- No accidents, 6 owners, personal use only
- 6cyl manual
- CarMax (In-stock online)
- Transfer available from FL to IL*
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Located in Doral, FL / 1,187 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
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: WP0AA2A83GK170143
Stock: 27634629
Certified Pre-Owned: No - $88,590good price$16,591 below market
- 28,779 miles
- No accidents, 6 owners, personal use
- 6cyl manual
- Carvana (In-stock online)
- Home delivery*
Close
Located in Richmond, VA / 606 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:
Listing Information:
VIN: WP0AC2A84GK197717
Stock: 2003841291
Certified Pre-Owned: No
Listed since: 06-26-2025 - New Listing$54,990good price$3,416 below market
- 12,549 miles
- No accidents, 1 owner, personal use
- 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: 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: WP0AB2A83EK193299
Stock: 2003820823
Certified Pre-Owned: No
Listed since: 06-13-2025 - New Listing$49,990good price$1,569 below market
- 34,261 miles
- No accidents, 7 owners, personal use
- 6cyl automated manual
- Carvana (In-stock online)
- Home delivery*
Close
Located in Phoenix, AZ / 1,447 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: WP0AB2A87EK192589
Stock: 2003828337
Certified Pre-Owned: No
Listed since: 06-28-2025 - $35,995fair price$175 below market
- 38,743 miles
- No accidents, 3 owners, personal use only
- 6cyl automated manual
- Greater Chicago Motors (23 mi away)
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Located in Glendale Heights, IL / 23 miles away from Chicago, IL
2011 Cayman Double BlackPDKHeated SeatsBose Upgrade soundsHeated steering wheelBluetoothCarfax CertifiedFABSPEED EXHUAST AND DOWNPIPESOriginal Exhaust...
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: WP0AA2A80BU761060
Stock: GCM7307
Certified Pre-Owned: No
Listed since: 04-24-2025 - $40,990fair price$799 below market
- 48,716 miles
- No accidents, 2 owners, personal use only
- 6cyl automated manual
- Carvana (In-stock online)
- Home delivery*
Close
Located in Cleveland, OH / 307 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: WP0AA2A84FK162826
Stock: 2003825946
Certified Pre-Owned: No
Listed since: 06-18-2025 - New Listing$49,990fair price$710 above market
- 15,802 miles
- No accidents, 1 owner, personal use only
- 6cyl automated manual
- Carvana (In-stock online)
- Home delivery*
Close
Located in St. Louis, MO / 262 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: WP0AA2A87GK171327
Stock: 2003846088
Certified Pre-Owned: No
Listed since: 06-27-2025 - $79,900fair price$1,811 above market
- 29,945 miles
- No accidents, 3 owners, personal use only
- 6cyl manual
- Gold Coast Motors (30 mi away)
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Located in Naperville, IL / 30 miles away from Chicago, IL
Vehicle Overview PURCHASE WITH CONFIDENCE FROM "GOLD COAST MOTORS"!! CALL SALES @ 6**.3**.9*** TODAY!! ***WE OFFER NATIONWIDE FINANCING WITH LOW RATES...
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: WP0AB2A87FK183134
Stock: 3072
Certified Pre-Owned: No
Listed since: 03-09-2025 - $30,900fair price$1,557 above market
- 58,368 miles
- No accidents, 3 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
Blue 2007 Porsche Cayman Recent Arrival! 2.7L H6 SMPI DOHC987110 CaymanDC Stone Grey Standard Leather56 Cobalt Blue MetallicP74 Bi-Xenon Lighting Syst...
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/29 Highway)
Listing Information:
VIN: WP0AA29867U760524
Stock: PPR4013
Certified Pre-Owned: No
Listed since: 06-29-2025 - New Listing
- 23,002 miles
- No accidents, 1 owner, personal use only
- 6cyl manual
- CarMax (In-stock online)
- Transfer available from CT to IL*
Close
Located in Hartford, CT / 769 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
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: WP0AA2A85FK163709
Stock: 27275390
Certified Pre-Owned: No - $27,995fair price$657 below market
- 36,778 miles
- 1 accident, 2 owners, personal use only
- 6cyl manual
- Indy Wholesale Direct (153 mi away)
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Located in Carmel, IN / 153 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/29 Highway)
Listing Information:
VIN: WP0AA29808U760228
Stock: 760228BB
Certified Pre-Owned: No
Listed since: 01-02-2025 - New Listing
- 41,382 miles
- No accidents, 2 owners, personal use only
- 6cyl automated manual
- Carvana (In-stock online)
- Home delivery*
Close
Located in Dallas, TX / 803 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: WP0AA2A80CS760178
Stock: 2003782754
Certified Pre-Owned: No
Listed since: 05-30-2025
Showing 1 - 21 out of 26 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.
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