American Airlines flights from Charleston, WV to Chicago

Recent searches for flights from Charleston, WV to Chicago

Jul 2026
From$392*
Updated: 4 hours ago
Round tripIEconomy
Aug 2026
From$268*
Updated: 20 hours ago
Round tripIEconomy
Sep 2026
From$268*
Updated: 4 hours ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $268
cmp-daily-histogram-bars-legend-max-price-aria-label $426
Displaying fares for July-2026
  • CRW–ORD, 07/30/26 – 08/06/26: From $426
    30

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    JUL

  • CRW–ORD, 07/31/26 – 08/07/26: From $392
    31

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  • CRW–ORD, 08/01/26 – 08/08/26: From $392
    01

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    AUG

  • CRW–ORD, 08/02/26 – 08/09/26: From $392
    02

    Su

  • CRW–ORD, 08/03/26 – 08/10/26: From $392
    03

    Mo

  • CRW–ORD, 08/04/26 – 08/11/26: From $392
    04

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  • CRW–ORD, 08/05/26 – 08/12/26: From $392
    05

    We

  • CRW–ORD, 08/06/26 – 08/13/26: From $328
    06

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  • CRW–ORD, 08/07/26 – 08/14/26: From $392
    07

    Fr

  • CRW–ORD, 08/08/26 – 08/15/26: From $328
    08

    Sa

  • CRW–ORD, 08/09/26 – 08/16/26: From $328
    09

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  • CRW–ORD, 08/10/26 – 08/17/26: From $328
    10

    Mo

  • CRW–ORD, 08/11/26 – 08/18/26: From $328
    11

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  • CRW–ORD, 08/12/26 – 08/19/26: From $328
    12

    We

  • CRW–ORD, 08/13/26 – 08/20/26: From $426
    13

    Th

  • CRW–ORD, 08/14/26 – 08/21/26: From $283
    14

    Fr

  • CRW–ORD, 08/15/26 – 08/22/26: From $283
    15

    Sa

  • CRW–ORD, 08/16/26 – 08/23/26: From $283
    16

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  • CRW–ORD, 08/17/26 – 08/24/26: From $283
    17

    Mo

  • CRW–ORD, 08/18/26 – 08/25/26: From $283
    18

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  • CRW–ORD, 08/19/26 – 08/26/26: From $283
    19

    We

  • CRW–ORD, 08/20/26 – 08/27/26: From $268
    20

    Th

  • CRW–ORD, 08/21/26 – 08/28/26: From $268
    21

    Fr

  • CRW–ORD, 08/22/26 – 08/29/26: From $268
    22

    Sa

  • CRW–ORD, 08/23/26 – 08/30/26: From $268
    23

    Su

  • CRW–ORD, 08/24/26 – 08/31/26: From $268
    24

    Mo

  • CRW–ORD, 08/25/26 – 09/01/26: From $268
    25

    Tu

  • CRW–ORD, 08/26/26 – 09/02/26: From $268
    26

    We

  • CRW–ORD: cmp-view-offers-disclaimer. Find Offers
    27

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  • CRW–ORD: cmp-view-offers-disclaimer. Find Offers
    28

    Fr

  • CRW–ORD, 08/29/26 – 09/05/26: From $268
    29

    Sa

    • range$268-$426

    DisclaimerFares displayed have been collected within the last 24hrs and may no longer be available at time of booking. Modifying this information may result in a different fare. To find the most updated fare, please visit aa.com. Fares listed may be Basic Economy, which class is subject to additional terms and conditions. Additional baggage fees and charges for optional products and services may apply.

    Find deals on Charleston, WV to Chicago flights

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    keyboard_arrow_down

    Charleston, WV (CRW)to

    Chicago (ORD)
    08/29/26 - 09/05/26

    Round trip

    Economy

    from
    $268Fare subject to changes
    Updated: 20 hours ago

    Charleston, WV (CRW)to

    Chicago (ORD)
    10/24/26 - 10/31/26

    Round trip

    Economy

    from
    $268Fare subject to changes
    Updated: 4 hours ago

    Charleston, WV (CRW)to

    Chicago (ORD)
    09/02/26 - 09/09/26

    Round trip

    Economy

    from
    $268Fare subject to changes
    Updated: 4 hours ago

    Charleston, WV (CRW)to

    Chicago (ORD)
    09/09/26 - 09/16/26

    Round trip

    Economy

    from
    $268Fare subject to changes
    Updated: 4 hours ago

    Charleston, WV (CRW)to

    Chicago (ORD)
    09/10/26 - 09/17/26

    Round trip

    Economy

    from
    $268Fare subject to changes
    Updated: 4 hours ago

    Charleston, WV (CRW)to

    Chicago (ORD)
    09/17/26 - 09/24/26

    Round trip

    Economy

    from
    $268Fare subject to changes
    Updated: 4 hours ago

    Charleston, WV (CRW)to

    Chicago (ORD)
    09/23/26 - 09/30/26

    Round trip

    Economy

    from
    $268Fare subject to changes
    Updated: 4 hours ago

    Charleston, WV (CRW)to

    Chicago (ORD)
    08/20/26 - 08/27/26

    Round trip

    Economy

    from
    $268Fare subject to changes
    Updated: 4 hours ago

    *Fares displayed have been collected within the last 24hrs and may no longer be available at time of booking. Some fares listed may include one or more connections that are Basic Economy, which class is subject to additional terms and conditions. Modifying this information may result in a different fare. To find the most updated fare, please visit aa.com. Additional baggage fees and charges for optional products and services may apply.

    Finding cheap flights from Charleston, WV to Chicago

    Looking for lower fares on your trip from Charleston, WV to Chicago? Here are a few ways to save.

    • Book early: Booking 1 to 3 months ahead can help you find lower fares
    • Be flexible with dates: Midweek travel, like Tuesdays and Wednesdays, can be more affordable
    • Travel during less busy periods: Flying outside peak travel times can help find lower fares and avoid crowds

    Earn up to $500 back on your next American Airlines flight plus, 30,000 bonus miles. Offers vary elsewhere. Opens another site in a new window that may not meet accessibility guidelines.

    Upgrade your flight with Main Cabin Extra

    Make your trip more comfortable with Main Cabin Extra. Enjoy benefits like:

    • Extra legroom: More space with seats at the front of the Main Cabin or in exit rows.
    • Early boarding: Preferred Group 5 boarding allows easier access to overhead bins.
    • Complimentary drinks: Enjoy beer, wine and spirits on flights with full beverage service.

    Discover how Main Cabin Extra can enhance your trip.

    American Airlines flights from Charleston, WV to Chicago