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Used Porsche Cayman for Sale in Chicago, IL

Buy a luxurious Porsche Cayman in the Windy City
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20 listings
  • $49,990
    great price
    $9,708 below market
    9,999 miles
    No accidents, 3 Owners, Personal use only
    6cyl Automated Manual
    Carvana (In-stock online)
    Free home delivery*
    • Bluetooth
    • Navigation
    • Leather Seats
    • Upgraded Headlights
    • Power Driver Seat
    Close

    Located in Cleveland, OH / 308 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: WP0AA2A83GK170448
    Stock: 2002631337
    Certified Pre-Owned: No
    Listed since: 11-23-2023

  • Price Drop
    $33,998
    great price
    $5,620 below market
    50,056 miles
    1 Accident, 3 Owners, Rental vehicle
    6cyl Automated Manual
    CarMax (In-stock online)
    Delivery available*
    • Bluetooth
    • Navigation
    • Leather Seats
    • Power Driver Seat
    • Tire Pressure Warnin...
    Close

    Located in Naples, FL / 1,136 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: 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:

    24 Combined MPG (20 City/30 Highway)

    Listing Information:

    VIN: WP0AA2A81EK172602
    Stock: 22456491
    Certified Pre-Owned: No

  • Price Drop
    $38,990
    good price
    $2,888 below market
    65,964 miles
    No accidents, 4 Owners, Personal use only
    6cyl Automated Manual
    Carvana (In-stock online)
    Free home delivery*
    • Bluetooth
    • Navigation
    • Leather Seats
    • Power Driver Seat
    • Tire Pressure Warnin...
    Close

    Located in Phoenix, AZ / 1,446 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: WP0AA2A80FK160698
    Stock: 2002698714
    Certified Pre-Owned: No
    Listed since: 01-19-2024

  • New Listing
    $53,990
    good price
    $3,270 below market
    23,841 miles
    No accidents, 3 Owners, Personal use
    6cyl Manual
    Carvana (In-stock online)
    Free home delivery*
    • Bluetooth
    • Navigation
    • Leather Seats
    • Upgraded Headlights
    • Power Driver Seat
    Close

    Located in Philadelphia, PA / 666 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: WP0AB2A86EK192230
    Stock: 2002760549
    Certified Pre-Owned: No
    Listed since: 02-20-2024

  • New Listing
    $43,998
    good price
    $2,864 below market
    38,615 miles
    No accidents, 2 Owners, Personal use only
    6cyl Automated Manual
    CarMax (In-stock online)
    Delivery available*
    • Bluetooth
    • Navigation
    • Leather Seats
    • Power Driver Seat
    • Tire Pressure Warnin...
    Close

    Located in Virginia Beach, VA / 707 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: WP0AA2A80GK170083
    Stock: 25538635
    Certified Pre-Owned: No

  • New Listing
    $44,998
    good price
    $2,949 below market
    58,403 miles
    6cyl Automated Manual
    CarMax (In-stock online)
    Delivery available*
    • Bluetooth
    • Navigation
    • Leather Seats
    • Upgraded Headlights
    • Power Driver Seat
    Close

    Located in Bristol, TN / 465 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:

    23 Combined MPG (20 City/28 Highway)

    Listing Information:

    VIN: WP0AB2A88EK193136
    Stock: 24441989
    Certified Pre-Owned: No

  • Price Drop
    $41,590
    good price
    $2,549 below market
    31,348 miles
    1 Accident, 5 Owners, Corporate fleet vehicle
    6cyl Automated Manual
    Carvana (In-stock online)
    Free home delivery*
    • Bluetooth
    • Navigation
    • Leather Seats
    • Power Driver Seat
    • Tire Pressure Warnin...
    Close

    Located in Tampa, FL / 1,005 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: 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:

    24 Combined MPG (20 City/30 Highway)

    Listing Information:

    VIN: WP0AA2A8XEK172193
    Stock: 2002649900
    Certified Pre-Owned: No
    Listed since: 02-02-2024

  • $24,950
    good price
    $1,975 below market
    44,555 miles
    2 Accidents, 1 Owner, Personal use only
    6cyl Automatic
    Revved Motors (18 mi away)
    • Leather Seats
    • Power Driver Seat
    • Tire Pressure Warnin...
    • Alarm
    • Trip Computer
    Close

    Located in Addison, IL / 18 miles away from Chicago, IL

    Vehicle Overview Please remember, every one of our cars has been enjoyed by their original owners, and these are not factory-new cars. This means they...

    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: WP0AA29848U762516
    Stock: D709
    Certified Pre-Owned: No
    Listed since: 10-21-2023

  • Price Drop
    11,973 miles
    No accidents, 3 Owners, Personal use
    6cyl Automated Manual
    Carvana (In-stock online)
    Free home delivery*
    • Bluetooth
    • Navigation
    • Leather Seats
    • Power Driver Seat
    • Tire Pressure Warnin...
    Close

    Located in Philadelphia, PA / 666 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: WP0AA2A88FK162974
    Stock: 2002669227
    Certified Pre-Owned: No
    Listed since: 01-17-2024

  • 36,198 miles
    1 Accident, 1 Owner, Personal use
    6cyl Manual
    Carvana (In-stock online)
    Free home delivery*
    • Bluetooth
    • Navigation
    • Leather Seats
    • Upgraded Headlights
    • Power Driver Seat
    Close

    Located in Dallas, TX / 802 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: WP0AB2A87EK192253
    Stock: 2002715476
    Certified Pre-Owned: No
    Listed since: 02-10-2024

  • New Listing
    $44,990
    fair price
    $1,077 above market
    32,285 miles
    No accidents, 4 Owners, Personal use
    6cyl Manual
    Carvana (In-stock online)
    Home delivery*
    • Bluetooth
    • Navigation
    • Leather Seats
    • Power Driver Seat
    • Tire Pressure Warnin...
    Close

    Located in Richmond, VA / 607 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: WP0AA2A89EK170841
    Stock: 2002735503
    Certified Pre-Owned: No
    Listed since: 02-06-2024

  • New Listing
    $35,995
    fair price
    $1,292 above market
    43,111 miles
    No accidents, 2 Owners, Personal use
    6cyl Automatic
    CarNeeD (22 mi away)
    • Leather Seats
    • Power Driver Seat
    • Tire Pressure Warnin...
    • Alarm
    • Trip Computer
    Close

    Located in Northbrook, IL / 22 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: WP0AB298X8U780564
    Stock: ND1464
    Certified Pre-Owned: No
    Listed since: 02-18-2024

  • New Listing
    $40,990
    fair price
    $1,635 above market
    54,043 miles
    No accidents, 3 Owners, Personal use
    6cyl Manual
    Carvana (In-stock online)
    Free home delivery*
    • Bluetooth
    • Navigation
    • Leather Seats
    • Power Driver Seat
    • Tire Pressure Warnin...
    Close

    Located in Birmingham, AL / 579 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: WP0AA2A89FK162028
    Stock: 2002700906
    Certified Pre-Owned: No
    Listed since: 02-21-2024

  • 7,957 miles
    No accidents, 2 Owners, Personal use
    6cyl Manual
    Carvana (In-stock online)
    Free home delivery*
    • Bluetooth
    • Navigation
    • Leather Seats
    • Power Driver Seat
    • Tire Pressure Warnin...
    Close

    Located in Dallas, TX / 802 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: WP0AA2A81EK174060
    Stock: 2002711011
    Certified Pre-Owned: No
    Listed since: 01-24-2024

  • 31,816 miles
    1 Accident, 3 Owners, Personal use only
    6cyl Manual
    CarMax (In-stock online)
    Delivery available*
    • Bluetooth
    • Navigation
    • Leather Seats
    • Upgraded Headlights
    • Power Driver Seat
    Close

    Located in Fort Worth, TX / 818 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:

    24 Combined MPG (20 City/30 Highway)

    Listing Information:

    VIN: WP0AA2A8XGK170477
    Stock: 25257087
    Certified Pre-Owned: No

  • 20,582 miles
    No accidents, 3 Owners, Personal use only
    6cyl Manual
    Carvana (In-stock online)
    Free home delivery*
    • Leather Seats
    • Power Driver Seat
    • Tire Pressure Warnin...
    • Alarm
    • Trip Computer
    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: WP0AA29849U760380
    Stock: 2002746079
    Certified Pre-Owned: No
    Listed since: 02-14-2024

  • New Listing
    $47,998
    fair price
    $790 above market
    56,308 miles
    6cyl Manual
    CarMax (In-stock online)
    Delivery available*
    • Bluetooth
    • Navigation
    • Leather Seats
    • Upgraded Headlights
    • Power Driver Seat
    Close

    Located in Bakersfield, CA / 1,744 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:

    23 Combined MPG (20 City/28 Highway)

    Listing Information:

    VIN: WP0AB2A84FK181227
    Stock: 24154286
    Certified Pre-Owned: No

  • 23,892 miles
    No accidents, 4 Owners, Corporate fleet vehicle
    6cyl Automated Manual
    Chicago Auto Place (20 mi away)
    • Bluetooth
    • Navigation
    • Leather Seats
    • Upgraded Headlights
    • Power Driver Seat
    Close

    Located in Downers Grove, IL / 20 miles away from Chicago, IL

    Premium Options Photo Finance Contact Thank you for visiting another one of Chicago Auto Place's exclusive listings! CALL US NOW FOR A FREE QUOTE 6**...

    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: WP0AB2A80EK193485
    Stock: H8517
    Certified Pre-Owned: No
    Listed since: 12-16-2023

  • New Listing
    108,820 miles
    No accidents, 1 Owner, Personal use
    6cyl Automated Manual
    Driveway (In-stock online)
    Home delivery*
    • Leather Seats
    • Power Driver Seat
    • Tire Pressure Warnin...
    • Alarm
    • Trip Computer
    Close

    Located in Fontana, CA / 1,699 miles away from Chicago, IL

    High Demand,Leather Seats,Flat 6 Cylinder Engine,Power Door Locks,Gasoline Fuel,Remote Trunk Release,CD Player,ABS,Power Passenger Seat,Rear Wheel Dri...

    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: WP0AA2A87CS760274
    Stock: CS760274P
    Certified Pre-Owned: No

  • 73,423 miles
    1 Accident, 3 Owners, Personal use
    6cyl Automated Manual
    CarMax (In-stock online)
    Delivery available*
    • Bluetooth
    • Navigation
    • Leather Seats
    • Power Driver Seat
    • Tire Pressure Warnin...
    Close

    Located in Tallahassee, FL / 810 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:

    24 Combined MPG (20 City/30 Highway)

    Listing Information:

    VIN: WP0AA2A86EK170795
    Stock: 23964192
    Certified Pre-Owned: No

1
Showing 1 - 20 out of 20 listings

Consumer Reviews for the Porsche Cayman

Read recent reviews for the Porsche Cayman
Overall Consumer Rating
4.7 out of 5 stars141 Reviews
Write a vehicle reviewSee all 141 reviews
  • 5 star
    (89%)
  • 4 star
    (5%)
  • 3 star
    (2%)
  • 2 star
    (1%)
  • 1 star
    (2%)
5 out of 5 stars

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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