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Used Chevrolet Silverado 1500 Custom Trail Boss for Sale in Chicago, IL

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    High Demand
    New 2026 Chevrolet Silverado 1500 Custom Trail Boss w/ Turbomax Blackout Package
    48,914
    MSRP$56,640
    Dealer Fees Included
    Similar Match
    Castle Chevrolet
    (331) 209-8867
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    Certified 2023 Chevrolet Silverado 1500 Custom Trail Boss

    2023 Chevrolet Silverado 1500

    • Custom Trail Boss
    • 52K mi
    37,183
    Great Price
    Dealer Fees Included
    No Accidents
    Sponsored by Phillips Chevrolet
    • 27.67 mi. away
    • Online Paperwork
    Call
    Certified 2024 Chevrolet Silverado 1500 Custom Trail Boss

    2024 Chevrolet Silverado 1500

    • Custom Trail Boss
    • 84K mi
    35,349
    Good Price
    Dealer Fees Included
    No Accidents
    Sponsored by Phillips Chevrolet of Bradley
    • 50.13 mi. away
    • Online Paperwork
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    Used 2024 Chevrolet Silverado 1500 Custom Trail Boss
    Used

    2024 Chevrolet Silverado 1500

    • Custom Trail Boss
    • 12K mi
    43,813
    Great Price
    Dealer Fees Included
    No Accidents
    Sponsored by Zeigler Chevrolet Schaumburg
    • 24.39 mi. away
    • Online Paperwork
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    Used 2024 Chevrolet Silverado 1500 Custom Trail Boss w/ LPO, Dark Essentials Package
    Used

    2024 Chevrolet Silverado 1500

    • Custom Trail Boss
    • 17K mi
    40,149
    Great Price
    Dealer Fees Included
    No Accidents
    Team Honda
    • 33.55 mi. away
    • Online Paperwork
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    Certified 2024 Chevrolet Silverado 1500 Custom Trail Boss w/ Turbomax Blackout Package

    2024 Chevrolet Silverado 1500

    • Custom Trail Boss
    • 25K mi Mileage Value
    40,136
    Great Price
    Dealer Fees Included
    No Accidents
    ADVANTAGE BUICK GMC CADILLAC
    • 13.58 mi. away
    Call
    New 2026 Chevrolet Silverado 1500 Custom Trail Boss w/ Dark Appearance Package
    Consider Buying New

    2026 Chevrolet Silverado 1500

    • Custom Trail Boss
    • 7 mi
    46,185
    Team Chevrolet
    • 40.42 mi. away
    • Online Paperwork
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    Used 2024 Chevrolet Silverado 1500 Custom Trail Boss
    Used

    2024 Chevrolet Silverado 1500

    • Custom Trail Boss
    • 12K mi
    43,813
    Great Price
    Dealer Fees Included
    No Accidents
    Zeigler Chevrolet Schaumburg
    • 24.39 mi. away
    • Online Paperwork
    Call
    Used 2019 Chevrolet Silverado 1500 Custom Trail Boss w/ Custom Convenience Package
    Used

    2019 Chevrolet Silverado 1500

    • Custom Trail Boss
    • 125K mi
    24,500
    No Accidents
    Private Seller Exchange
    • 21.32 mi. away
    • Buy Online. Clean title. No Hassle
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    Item 1 of 4.
    Used 2024 Chevrolet Silverado 1500 Custom Trail Boss
    Used

    2024 Chevrolet Silverado 1500

    • Custom Trail Boss
    • 12K mi
    43,813
    Great Price
    Dealer Fees Included
    No Accidents
    Call
    360°
    Certified 2023 Chevrolet Silverado 1500 Custom Trail Boss

    2023 Chevrolet Silverado 1500

    • Custom Trail Boss
    • 52K mi
    37,183
    Great Price
    Dealer Fees Included
    No Accidents
    Phillips Chevrolet
    • 27.67 mi. away
    • Online Paperwork
    Call
    360°
    Certified 2024 Chevrolet Silverado 1500 Custom Trail Boss w/ Turbomax Blackout Package

    2024 Chevrolet Silverado 1500

    • Custom Trail Boss
    • 35K mi
    39,293
    Great Price
    Dealer Fees Included
    No Accidents
    Phillips Chevrolet
    • 27.67 mi. away
    • Online Paperwork
    Call
    Used 2020 Chevrolet Silverado 1500 Custom Trail Boss w/ Custom Convenience Package
    Used

    2020 Chevrolet Silverado 1500

    • Custom Trail Boss
    • 77K mi
    30,224
    Great Price
    Dealer Fees Included
    Kunes of Woodstock CDJR
    • 50.19 mi. away
    • Online Paperwork
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    Certified 2024 Chevrolet Silverado 1500 Custom Trail Boss

    2024 Chevrolet Silverado 1500

    • Custom Trail Boss
    • 23K mi
    43,910
    Good Price
    Dealer Fees Included
    No Accidents
    Ray Chevrolet
    • 45.83 mi. away
    • Online Paperwork
    Call
    Used 2024 Chevrolet Silverado 1500 Custom Trail Boss

    2024 Chevrolet Silverado 1500

    • Custom Trail Boss
    • 79K mi
    32,906
    Good Price
    Dealer Fees Included
    No Accidents
    Kunes Ford Of Antioch
    • 47.09 mi. away
    • Online Paperwork
    Call
    Used 2024 Chevrolet Silverado 1500 Custom Trail Boss
    Used

    2024 Chevrolet Silverado 1500

    • Custom Trail Boss
    • 104K mi
    30,908
    Good Price
    Dealer Fees Included
    No Accidents
    Castle Chevrolet GMC Cadillac of McHenry
    • 44.74 mi. away
    Call
    Price Drop
    Used 2021 Chevrolet Silverado 1500 Custom Trail Boss
    Used

    2021 Chevrolet Silverado 1500

    • Custom Trail Boss
    • 60K mi
    32,897
    No Accidents
    GRAFF CHEVROLET OF CHESTERTON
    • 32.83 mi. away
    Call
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    Used 2020 Chevrolet Silverado 1500 Custom Trail Boss w/ Custom Convenience Package
    Used

    2020 Chevrolet Silverado 1500

    • Custom Trail Boss
    • 95K mi
    25,258
    Great Price
    Dealer Fees Included
    No Accidents
    Chevrolet of Merrillville
    • 30.28 mi. away
    Call
    Used 2019 Chevrolet Silverado 1500 Custom Trail Boss w/ Custom Convenience Package
    Used

    2019 Chevrolet Silverado 1500

    • Custom Trail Boss
    • 93K mi
    27,975
    No Accidents
    Crase Auto Connection
    • 43.33 mi. away
    • Online Paperwork
    • Delivery
    Call
    Used 2021 Chevrolet Silverado 1500 Custom Trail Boss w/ Safety Confidence Package
    Used

    2021 Chevrolet Silverado 1500

    • Custom Trail Boss
    • 79K mi
    33,550
    Dealer Fees Included
    No Accidents
    Rizza Buick Cadillac GMC.
    • 21.21 mi. away
    Call
    Used 2024 Chevrolet Silverado 1500 Custom Trail Boss
    Used

    2024 Chevrolet Silverado 1500

    • Custom Trail Boss
    • 33K mi
    43,370
    Good Price
    Dealer Fees Included
    No Accidents
    Ray Chevrolet
    • 45.83 mi. away
    • Online Paperwork
    Call
    Used 2025 Chevrolet Silverado 1500 Custom Trail Boss w/ Dark Appearance Package
    Used

    2025 Chevrolet Silverado 1500

    • Custom Trail Boss
    • 32K mi
    42,807
    No Accidents
    GRAFF TOYOTA OF CHESTERTON
    • 32.85 mi. away
    Call
    Certified 2024 Chevrolet Silverado 1500 Custom Trail Boss

    2024 Chevrolet Silverado 1500

    • Custom Trail Boss
    • 84K mi
    35,349
    Good Price
    Dealer Fees Included
    No Accidents
    Phillips Chevrolet of Bradley
    • 50.13 mi. away
    • Online Paperwork
    Call
    360°
    Certified 2023 Chevrolet Silverado 1500 Custom Trail Boss

    2023 Chevrolet Silverado 1500

    • Custom Trail Boss
    • 52K mi
    37,183
    Great Price
    Dealer Fees Included
    No Accidents
    Sponsored by Phillips Chevrolet
    • 27.67 mi. away
    • Online Paperwork
    Call
    Newly Listed
    Used 2021 Chevrolet Silverado 1500 Custom Trail Boss
    Used

    2021 Chevrolet Silverado 1500

    • Custom Trail Boss
    • 32K mi
    36,278
    Dealer Fees Included
    Elmhurst Ford
    • 16.69 mi. away
    • Online Paperwork
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    Newly Listed
    Used 2022 Chevrolet Silverado 1500 Custom Trail Boss
    Used

    2022 Chevrolet Silverado 1500

    • Custom Trail Boss
    • 99K mi
    28,995
    Dealer Fees Included
    No Accidents
    Napletons Arlington Heights Chrysler Dodge Jeep RAM
    • 25.99 mi. away
    Call
    Used 2026 Chevrolet Silverado 1500 Custom Trail Boss
    Used

    2026 Chevrolet Silverado 1500

    • Custom Trail Boss
    • 8K mi
    42,404
    Great Price
    Dealer Fees Included
    No Accidents
    Kunes Lakes Chevrolet
    • 29.71 mi. away
    Call
    Used 2022 Chevrolet Silverado 1500 Custom Trail Boss w/ LPO, Dark Essentials Package
    Used

    2022 Chevrolet Silverado 1500

    • Custom Trail Boss
    • 37K mi
    35,635
    Great Price
    Dealer Fees Included
    No Accidents
    Huntley Ford
    • 44.29 mi. away
    • Online Paperwork
    Call
    Used 2025 Chevrolet Silverado 1500 Custom Trail Boss
    Used

    2025 Chevrolet Silverado 1500

    • Custom Trail Boss
    • 34K mi
    43,764
    Great Price
    Dealer Fees Included
    No Accidents
    Castle Subaru
    • 31.08 mi. away
    • Online Paperwork
    Call
    Used 2022 Chevrolet Silverado 1500 Custom Trail Boss
    Used

    2022 Chevrolet Silverado 1500

    • Custom Trail Boss
    • 82K mi
    31,500
    Great Price
    No Additional Dealer Fees
    No Accidents
    Nelson Automotive
    • 21.33 mi. away
    Call
    Used 2021 Chevrolet Silverado 1500 Custom Trail Boss
    Used

    2021 Chevrolet Silverado 1500

    • Custom Trail Boss
    • 44K mi
    34,985
    No Accidents
    Star Auto Works
    • 20.55 mi. away
    Call
    Used 2023 Chevrolet Silverado 1500 Custom Trail Boss
    Used

    2023 Chevrolet Silverado 1500

    • Custom Trail Boss
    • 74K mi
    36,399
    No Accidents
    Rocky Mountain Eurosport Parker - Chicago
    • Delivery
    Call
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