American Airlines flights from Charlottesville to Chicago

Recent searches for flights from Charlottesville to Chicago

Sep 2026
From$319*
Updated: 3 hours ago
Round tripIEconomy
Oct 2026
From$309*
Updated: 3 hours ago
Round tripIEconomy
Nov 2026
From$299*
Updated: 3 hours ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $319
cmp-daily-histogram-bars-legend-max-price-aria-label $579
Displaying fares for September-2026
  • CHO–ORD: cmp-view-offers-disclaimer. Find Offers
    01

    Tu

    SEP

  • CHO–ORD, 09/02/26 – 09/09/26: From $475
    02

    We

  • CHO–ORD, 09/03/26 – 09/10/26: From $504
    03

    Th

  • CHO–ORD, 09/04/26 – 09/11/26: From $579
    04

    Fr

  • CHO–ORD, 09/05/26 – 09/12/26: From $521
    05

    Sa

  • CHO–ORD, 09/06/26 – 09/13/26: From $504
    06

    Su

  • CHO–ORD, 09/07/26 – 09/14/26: From $504
    07

    Mo

  • CHO–ORD, 09/08/26 – 09/15/26: From $394
    08

    Tu

  • CHO–ORD, 09/09/26 – 09/16/26: From $386
    09

    We

  • CHO–ORD, 09/10/26 – 09/17/26: From $496
    10

    Th

  • CHO–ORD, 09/11/26 – 09/18/26: From $496
    11

    Fr

  • CHO–ORD, 09/12/26 – 09/19/26: From $386
    12

    Sa

  • CHO–ORD, 09/13/26 – 09/20/26: From $504
    13

    Su

  • CHO–ORD, 09/14/26 – 09/21/26: From $469
    14

    Mo

  • CHO–ORD, 09/15/26 – 09/22/26: From $339
    15

    Tu

  • CHO–ORD, 09/16/26 – 09/23/26: From $339
    16

    We

  • CHO–ORD, 09/17/26 – 09/24/26: From $469
    17

    Th

  • CHO–ORD, 09/18/26 – 09/25/26: From $469
    18

    Fr

  • CHO–ORD, 09/19/26 – 09/26/26: From $339
    19

    Sa

  • CHO–ORD, 09/20/26 – 09/27/26: From $339
    20

    Su

  • CHO–ORD, 09/21/26 – 09/28/26: From $339
    21

    Mo

  • CHO–ORD, 09/22/26 – 09/29/26: From $319
    22

    Tu

  • CHO–ORD, 09/23/26 – 09/30/26: From $319
    23

    We

  • CHO–ORD, 09/24/26 – 10/01/26: From $319
    24

    Th

  • CHO–ORD, 09/25/26 – 10/02/26: From $339
    25

    Fr

  • CHO–ORD, 09/26/26 – 10/03/26: From $319
    26

    Sa

  • CHO–ORD, 09/27/26 – 10/04/26: From $449
    27

    Su

  • CHO–ORD, 09/28/26 – 10/05/26: From $319
    28

    Mo

  • CHO–ORD, 09/29/26 – 10/01/26: From $557
    29

    Tu

  • CHO–ORD: cmp-view-offers-disclaimer. Find Offers
    30

    We

    • range$319-$579

    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 Charlottesville to Chicago flights

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    Charlottesville (CHO)to

    Chicago (ORD)
    11/01/26 - 11/08/26

    Round trip

    Economy

    from
    $299Fare subject to changes
    Updated: 3 hours ago

    Charlottesville (CHO)to

    Chicago (ORD)
    11/02/26 - 11/09/26

    Round trip

    Economy

    from
    $299Fare subject to changes
    Updated: 3 hours ago

    Charlottesville (CHO)to

    Chicago (ORD)
    11/04/26 - 11/11/26

    Round trip

    Economy

    from
    $299Fare subject to changes
    Updated: 3 hours ago

    Charlottesville (CHO)to

    Chicago (ORD)
    11/25/26 - 12/02/26

    Round trip

    Economy

    from
    $299Fare subject to changes
    Updated: 3 hours ago

    Charlottesville (CHO)to

    Chicago (ORD)
    11/05/26 - 11/12/26

    Round trip

    Economy

    from
    $299Fare subject to changes
    Updated: 3 hours ago

    Charlottesville (CHO)to

    Chicago (ORD)
    11/07/26 - 11/14/26

    Round trip

    Economy

    from
    $299Fare subject to changes
    Updated: 3 hours ago

    Charlottesville (CHO)to

    Chicago (ORD)
    11/08/26 - 11/15/26

    Round trip

    Economy

    from
    $299Fare subject to changes
    Updated: 3 hours ago

    Charlottesville (CHO)to

    Chicago (ORD)
    11/09/26 - 11/16/26

    Round trip

    Economy

    from
    $299Fare subject to changes
    Updated: 3 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 Charlottesville to Chicago

    Looking for lower fares on your trip from Charlottesville 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 Charlottesville to Chicago