American Airlines flights from Miami to Chicago

Recent searches for flights from Miami to Chicago

Aug 2026
From$453*
Updated: 22 hours ago
Round tripIEconomy
Sep 2026
From$171*
Updated: 14 hours ago
Round tripIEconomy
Oct 2026
From$171*
Updated: 14 hours ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $171
cmp-daily-histogram-bars-legend-max-price-aria-label $563
Displaying fares for August-2026
  • MIA–ORD, 08/23/26 – 08/26/26: From $528
    23

    Su

    AUG

  • MIA–CHI, 08/24/26 – 08/31/26: From $563
    24

    Mo

  • MIA–ORD, 08/25/26 – 09/01/26: From $493
    25

    Tu

  • MIA–CHI, 08/26/26 – 09/02/26: From $493
    26

    We

  • MIA–ORD, 08/27/26 – 09/03/26: From $563
    27

    Th

  • MIA–CHI, 08/28/26 – 09/04/26: From $563
    28

    Fr

  • MIA–ORD, 08/29/26 – 10/09/26: From $453
    29

    Sa

  • MIA–ORD, 08/30/26 – 09/06/26: From $563
    30

    Su

  • MIA–ORD, 08/31/26 – 09/02/26: From $528
    31

    Mo

  • MIA–CHI, 09/01/26 – 09/08/26: From $493
    01

    Tu

    SEP

  • MIA–CHI, 09/02/26 – 09/09/26: From $493
    02

    We

  • MIA–CHI, 09/03/26 – 09/10/26: From $563
    03

    Th

  • MIA–ORD, 09/04/26 – 09/09/26: From $528
    04

    Fr

  • MIA–CHI, 09/05/26 – 09/12/26: From $430
    05

    Sa

  • MIA–CHI, 09/06/26 – 09/13/26: From $433
    06

    Su

  • MIA–CHI, 09/07/26 – 09/14/26: From $367
    07

    Mo

  • MIA–CHI, 09/08/26 – 09/15/26: From $332
    08

    Tu

  • MIA–ORD, 09/09/26 – 09/16/26: From $269
    09

    We

  • MIA–CHI, 09/10/26 – 09/17/26: From $269
    10

    Th

  • MIA–ORD, 09/11/26 – 09/14/26: From $269
    11

    Fr

  • MIA–ORD, 09/12/26 – 09/19/26: From $171
    12

    Sa

  • MIA–CHI, 09/13/26 – 09/20/26: From $499
    13

    Su

  • MIA–ORD, 09/14/26 – 09/21/26: From $171
    14

    Mo

  • MIA–CHI, 09/15/26 – 09/22/26: From $171
    15

    Tu

  • MIA–CHI, 09/16/26 – 09/23/26: From $171
    16

    We

  • MIA–CHI, 09/17/26 – 09/24/26: From $171
    17

    Th

  • MIA–CHI, 09/18/26 – 09/25/26: From $191
    18

    Fr

  • MIA–CHI, 09/19/26 – 09/26/26: From $171
    19

    Sa

  • MIA–ORD, 09/20/26 – 09/24/26: From $301
    20

    Su

  • MIA–CHI: cmp-view-offers-disclaimer. Find Offers
    21

    Mo

  • MIA–CHI, 09/22/26 – 09/29/26: From $171
    22

    Tu

    • range$171-$563

    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 Miami to Chicago flights

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    Miami (MIA)to

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

    Round trip

    Economy

    from
    $171Fare subject to changes
    Updated: 4 hours ago

    Miami (MIA)to

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

    Round trip

    Economy

    from
    $171Fare subject to changes
    Updated: 4 hours ago

    Miami (MIA)to

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

    Round trip

    Economy

    from
    $171Fare subject to changes
    Updated: 4 hours ago

    Miami (MIA)to

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

    Round trip

    Economy

    from
    $171Fare subject to changes
    Updated: 4 hours ago

    Miami (MIA)to

    Chicago (ORD)
    10/06/26 - 10/13/26

    Round trip

    Economy

    from
    $171Fare subject to changes
    Updated: 4 hours ago

    Miami (MIA)to

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

    Round trip

    Economy

    from
    $171Fare subject to changes
    Updated: 4 hours ago

    Miami (MIA)to

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

    Round trip

    Economy

    from
    $171Fare subject to changes
    Updated: 4 hours ago

    Miami (MIA)to

    Chicago (ORD)
    09/22/26 - 09/29/26

    Round trip

    Economy

    from
    $171Fare subject to changes
    Updated: 14 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 Miami to Chicago

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