American Airlines flights from Midland to Chicago

Recent searches for flights from Midland to Chicago

Aug 2026
From$567*
Updated: 11 hours ago
Round tripIEconomy
Sep 2026
From$339*
Updated: 11 hours ago
Round tripIEconomy
Oct 2026
From$339*
Updated: 11 hours ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $339
cmp-daily-histogram-bars-legend-max-price-aria-label $851
Displaying fares for August-2026
  • MAF–ORD, 08/25/26 – 09/01/26: From $567
    25

    Tu

    AUG

  • MAF–ORD, 08/26/26 – 09/02/26: From $567
    26

    We

  • MAF–ORD, 08/27/26 – 09/03/26: From $665
    27

    Th

  • MAF–ORD, 08/28/26 – 09/04/26: From $665
    28

    Fr

  • MAF–ORD, 08/29/26 – 09/05/26: From $567
    29

    Sa

  • MAF–ORD, 08/30/26 – 09/06/26: From $665
    30

    Su

  • MAF–ORD, 08/31/26 – 09/07/26: From $851
    31

    Mo

  • MAF–ORD, 09/01/26 – 09/08/26: From $595
    01

    Tu

    SEP

  • MAF–ORD, 09/02/26 – 09/09/26: From $542
    02

    We

  • MAF–ORD, 09/03/26 – 09/10/26: From $636
    03

    Th

  • MAF–ORD, 09/04/26 – 09/11/26: From $636
    04

    Fr

  • MAF–ORD, 09/05/26 – 09/12/26: From $428
    05

    Sa

  • MAF–ORD, 09/06/26 – 09/13/26: From $428
    06

    Su

  • MAF–ORD, 09/07/26 – 09/14/26: From $497
    07

    Mo

  • MAF–ORD, 09/08/26 – 09/15/26: From $497
    08

    Tu

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

    We

  • MAF–ORD, 09/10/26 – 09/17/26: From $339
    10

    Th

  • MAF–ORD, 09/11/26 – 09/18/26: From $362
    11

    Fr

  • MAF–ORD, 09/12/26 – 09/19/26: From $339
    12

    Sa

  • MAF–ORD, 09/13/26 – 09/20/26: From $487
    13

    Su

  • MAF–ORD, 09/14/26 – 09/21/26: From $408
    14

    Mo

  • MAF–ORD, 09/15/26 – 09/22/26: From $408
    15

    Tu

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

    We

  • MAF–ORD, 09/17/26 – 09/24/26: From $408
    17

    Th

  • MAF–ORD, 09/18/26 – 09/25/26: From $385
    18

    Fr

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

    Sa

  • MAF–ORD, 09/20/26 – 09/27/26: From $447
    20

    Su

  • MAF–ORD: cmp-view-offers-disclaimer. Find Offers
    21

    Mo

  • MAF–ORD: cmp-view-offers-disclaimer. Find Offers
    22

    Tu

  • MAF–ORD: cmp-view-offers-disclaimer. Find Offers
    23

    We

  • MAF–ORD, 09/24/26 – 10/01/26: From $408
    24

    Th

    • range$339-$851

    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 Midland to Chicago flights

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    Midland (MAF)to

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

    Round trip

    Economy

    from
    $339Fare subject to changes
    Updated: 11 hours ago

    Midland (MAF)to

    Chicago (ORD)
    10/14/26 - 10/21/26

    Round trip

    Economy

    from
    $339Fare subject to changes
    Updated: 11 hours ago

    Midland (MAF)to

    Chicago (ORD)
    10/17/26 - 10/24/26

    Round trip

    Economy

    from
    $339Fare subject to changes
    Updated: 11 hours ago

    Midland (MAF)to

    Chicago (ORD)
    10/28/26 - 11/04/26

    Round trip

    Economy

    from
    $339Fare subject to changes
    Updated: 11 hours ago

    Midland (MAF)to

    Chicago (ORD)
    10/31/26 - 11/07/26

    Round trip

    Economy

    from
    $339Fare subject to changes
    Updated: 11 hours ago

    Midland (MAF)to

    Chicago (ORD)
    09/19/26 - 09/26/26

    Round trip

    Economy

    from
    $339Fare subject to changes
    Updated: 11 hours ago

    Midland (MAF)to

    Chicago (ORD)
    09/26/26 - 10/03/26

    Round trip

    Economy

    from
    $339Fare subject to changes
    Updated: 11 hours ago

    Midland (MAF)to

    Chicago (ORD)
    09/29/26 - 10/06/26

    Round trip

    Economy

    from
    $339Fare subject to changes
    Updated: 11 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 Midland to Chicago

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