American Airlines flights from Orlando to Chicago

Recent searches for flights from Orlando to Chicago

Sep 2026
From$307*
Updated: 2 hours ago
Round tripIEconomy
Oct 2026
From$219*
Updated: 2 hours ago
Round tripIEconomy
Nov 2026
From$219*
Updated: 2 hours ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $219
cmp-daily-histogram-bars-legend-max-price-aria-label $439
Displaying fares for September-2026
  • MCO–ORD, 09/15/26 – 09/19/26: From $381
    15

    Tu

    SEP

  • MCO–ORD, 09/16/26 – 09/23/26: From $371
    16

    We

  • MCO–ORD, 09/17/26 – 09/21/26: From $415
    17

    Th

  • MCO–ORD, 09/18/26 – 09/20/26: From $415
    18

    Fr

  • MCO–ORD, 09/19/26 – 09/26/26: From $395
    19

    Sa

  • MCO–ORD, 09/20/26 – 09/26/26: From $393
    20

    Su

  • MCO–ORD, 09/21/26 – 09/22/26: From $437
    21

    Mo

  • MCO–ORD, 09/22/26 – 09/29/26: From $395
    22

    Tu

  • MCO–ORD, 09/23/26 – 09/29/26: From $371
    23

    We

  • MCO–ORD, 09/24/26 – 10/01/26: From $439
    24

    Th

  • MCO–ORD, 09/25/26 – 09/28/26: From $415
    25

    Fr

  • MCO–ORD, 09/26/26 – 09/29/26: From $371
    26

    Sa

  • MCO–ORD, 09/27/26 – 10/04/26: From $439
    27

    Su

  • MCO–ORD, 09/28/26 – 10/05/26: From $345
    28

    Mo

  • MCO–ORD, 09/29/26 – 10/06/26: From $307
    29

    Tu

  • MCO–ORD, 09/30/26 – 10/06/26: From $307
    30

    We

  • MCO–ORD, 10/01/26 – 10/08/26: From $370
    01

    Th

    OCT

  • MCO–ORD, 10/02/26 – 10/09/26: From $361
    02

    Fr

  • MCO–ORD, 10/03/26 – 10/10/26: From $307
    03

    Sa

  • MCO–ORD, 10/04/26 – 10/08/26: From $355
    04

    Su

  • MCO–ORD, 10/05/26 – 10/12/26: From $251
    05

    Mo

  • MCO–ORD, 10/06/26 – 10/13/26: From $219
    06

    Tu

  • MCO–ORD, 10/07/26 – 10/14/26: From $219
    07

    We

  • MCO–ORD, 10/08/26 – 10/10/26: From $235
    08

    Th

  • MCO–ORD, 10/09/26 – 10/12/26: From $267
    09

    Fr

  • MCO–ORD, 10/10/26 – 10/17/26: From $219
    10

    Sa

  • MCO–ORD, 10/11/26 – 10/18/26: From $414
    11

    Su

  • MCO–ORD, 10/12/26 – 10/19/26: From $261
    12

    Mo

  • MCO–ORD: cmp-view-offers-disclaimer. Find Offers
    13

    Tu

  • MCO–ORD: cmp-view-offers-disclaimer. Find Offers
    14

    We

    • range$219-$439

    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 Orlando to Chicago flights

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    Orlando (MCO)to

    Chicago (ORD)
    10/20/26 - 10/27/26

    Round trip

    Economy

    from
    $219Fare subject to changes
    Updated: 2 hours ago

    Orlando (MCO)to

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

    Round trip

    Economy

    from
    $219Fare subject to changes
    Updated: 2 hours ago

    Orlando (MCO)to

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

    Round trip

    Economy

    from
    $219Fare subject to changes
    Updated: 2 hours ago

    Orlando (MCO)to

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

    Round trip

    Economy

    from
    $219Fare subject to changes
    Updated: 2 hours ago

    Orlando (MCO)to

    Chicago (ORD)
    11/10/26 - 11/17/26

    Round trip

    Economy

    from
    $219Fare subject to changes
    Updated: 2 hours ago

    Orlando (MCO)to

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

    Round trip

    Economy

    from
    $219Fare subject to changes
    Updated: 2 hours ago

    Orlando (MCO)to

    Chicago (ORD)
    10/27/26 - 11/03/26

    Round trip

    Economy

    from
    $219Fare subject to changes
    Updated: 2 hours ago

    Orlando (MCO)to

    Chicago (ORD)
    12/01/26 - 12/08/26

    Round trip

    Economy

    from
    $219Fare subject to changes
    Updated: 2 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.

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