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Best Deals on Used Convertibles for Sale in Chicago, IL

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Items 1 to 2 of 11.

    197 Matches

    Used 2018 Buick Cascada Sport Touring w/ Dark Effects Package
    Used
    • Sport Touring
    • 108K mi
    11,995
    See payment
    Great Price
    360°
    Used 2025 Porsche 718 Boxster Spyder RS
    Used
    • Spyder RS
    • 37 mi
    231,900
    See payment
    Good Price
    Certified 2024 Mercedes-Benz CLE 450 4MATIC Cabriolet
     Mercedes-Benz Certified
    • 4MATIC Cabriolet
    • 28K mi
    62,922
    See payment
    Great Price
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    Based on 4.5% APR for mos.
    Newly Listed
    Used 2023 Ford Mustang Premium
    Used
    • Premium
    • 60K mi
    22,000
    See payment
    Good Price
    Used 2025 Ford Mustang Premium
    Used
    • Premium
    • 20K mi
    37,534
    See payment
    Good Price
    Newly Listed
    New 2026 MAZDA MX-5 Miata Grand Touring
    Consider New, Similar Payment
    • Grand Touring
    • 4 mi
    Certified 2021 Porsche 911 Carrera
     Porsche Certified
    • Carrera
    • 0 mi
    126,991
    See payment
    Great Price
    Sponsored
    Certified
    • Carrera
    • 201 mi
    175,750
    See payment
    Great Price
    Certified 2024 Mercedes-Benz CLE 450 4MATIC Cabriolet
     Mercedes-Benz Certified
    • 4MATIC Cabriolet
    • 28K mi
    62,922
    See payment
    Great Price
    Certified 2025 Mercedes-Benz CLE 300 4MATIC Cabriolet
     Mercedes-Benz Certified
    • 4MATIC Cabriolet
    • 7K mi
    64,216
    See payment
    Good Price
    Used 2008 Porsche Boxster S
    24,999
    See payment
    Great Price
    Used 2022 Ford Mustang Premium
    CarBravo Certified
    • Premium
    • 73K mi
    19,700
    See payment
    Great Price
    Used 2025 Ford Mustang GT Premium
    Used
    • GT Premium
    • 6K mi
    53,998
    See payment
    Great Price
    Used 2023 Ford Mustang GT Premium
    Used
    • GT Premium
    • 42K mi
    33,800
    See payment
    Great Price
    Used 2022 BMW Z4 sDrive30i w/ Driving Assistance Package
    Used
    • sDrive30i
    • 62K mi
    27,995
    See payment
    Great Price
    Used 2024 Ford Mustang Premium
    Used
    • Premium
    • 42K mi
    28,625
    See payment
    Good Price
    Newly Listed
    Certified 2025 Porsche 718 Boxster Spyder RS
     Porsche Certified
    • Spyder RS
    • 1K mi
    209,000
    See payment
    Great Price
    Newly Listed
    Used 2024 BMW M850i xDrive Convertible
    Used
    • Convertible
    • 13K mi
    88,846
    See payment
    Great Price
    Certified 2026 Porsche 911 Carrera
     Porsche Certified
    • Carrera
    • 201 mi
    175,750
    See payment
    Great Price
    Used 2021 Audi R8 V10 performance w/ R8 Performance Design Package
    Used
    • V10 performance
    • 4K mi
    199,999
    See payment
    Good Price
    360°
    Used 2022 BMW Z4 M40i w/ Premium Package
    Used
    • M40i
    • 31K mi
    48,000
    See payment
    Great Price
    Certified 2025 MAZDA MX-5 Miata Grand Touring
     Mazda Certified
    • Grand Touring
    • 11K mi
    31,995
    See payment
    Good Price
    Certified 2025 MAZDA MX-5 Miata Grand Touring w/ Weather Package
     Mazda Certified
    • Grand Touring
    • 1K mi
    33,995
    See payment
    Good Price
    Used 2022 BMW M4 xDrive Competition w/ Executive Package
    Used
    • Competition
    • 26K mi
    64,800
    See payment
    Great Price
    Used 2017 Audi R8 V10
    Used
    • V10
    • 33K mi
    124,800
    See payment
    Good Price
    360°
    Certified 2024 BMW 430i xDrive Convertible w/ Convenience Package
     BMW Certified
    • Convertible
    • 5K mi
    53,500
    See payment
    Good Price
    360°
    Certified 2026 BMW Z4 sDrive30i
     BMW Certified
    • sDrive30i
    • 11K mi
    53,600
    See payment
    Great Price
    360°
    Certified 2025 Porsche 718 Boxster Spyder RS
     Porsche Certified
    • Spyder RS
    • 304 mi
    228,900
    See payment
    Great Price

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