American Airlines flights from Orlando to Chicago

Recent searches for flights from Orlando to Chicago

Aug 2026
From$247*
Updated: 2 hours ago
Round tripIEconomy
Sep 2026
From$235*
Updated: 21 hours ago
Round tripIEconomy
Oct 2026
From$257*
Updated: 2 hours ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $247
cmp-daily-histogram-bars-legend-max-price-aria-label $399
Displaying fares for August-2026
  • MCO–ORD, 08/04/26 – 08/08/26: From $355
    04

    Tu

    AUG

  • MCO–CHI, 08/05/26 – 08/12/26: From $355
    05

    We

  • MCO–ORD, 08/06/26 – 08/15/26: From $377
    06

    Th

  • MCO–ORD, 08/07/26 – 08/14/26: From $399
    07

    Fr

  • MCO–ORD, 08/08/26 – 08/15/26: From $365
    08

    Sa

  • MCO–ORD, 08/09/26 – 08/15/26: From $377
    09

    Su

  • MCO–CHI, 08/10/26 – 08/17/26: From $399
    10

    Mo

  • MCO–CHI, 08/11/26 – 08/18/26: From $355
    11

    Tu

  • MCO–ORD, 08/12/26 – 08/19/26: From $355
    12

    We

  • MCO–ORD, 08/13/26 – 08/20/26: From $399
    13

    Th

  • MCO–ORD, 08/14/26 – 08/19/26: From $377
    14

    Fr

  • MCO–CHI, 08/15/26 – 08/22/26: From $365
    15

    Sa

  • MCO–ORD, 08/16/26 – 08/24/26: From $328
    16

    Su

  • MCO–CHI, 08/17/26 – 08/24/26: From $399
    17

    Mo

  • MCO–CHI, 08/18/26 – 08/25/26: From $306
    18

    Tu

  • MCO–ORD, 08/19/26 – 08/26/26: From $306
    19

    We

  • MCO–CHI, 08/20/26 – 08/27/26: From $328
    20

    Th

  • MCO–CHI, 08/21/26 – 08/28/26: From $376
    21

    Fr

  • MCO–ORD, 08/22/26 – 08/29/26: From $306
    22

    Sa

  • MCO–ORD, 08/23/26 – 08/25/26: From $328
    23

    Su

  • MCO–ORD, 08/24/26 – 08/28/26: From $305
    24

    Mo

  • MCO–CHI, 08/25/26 – 09/01/26: From $257
    25

    Tu

  • MCO–ORD, 08/26/26 – 09/02/26: From $257
    26

    We

  • MCO–ORD, 08/27/26 – 09/03/26: From $257
    27

    Th

  • MCO–CHI, 08/28/26 – 09/04/26: From $351
    28

    Fr

  • MCO–ORD, 08/29/26 – 09/05/26: From $247
    29

    Sa

  • MCO–ORD, 08/30/26 – 09/06/26: From $318
    30

    Su

  • MCO–CHI, 08/31/26 – 09/07/26: From $257
    31

    Mo

  • MCO–ORD, 09/01/26 – 09/02/26: From $257
    01

    Tu

    SEP

  • MCO–ORD, 09/02/26 – 09/05/26: From $247
    02

    We

  • MCO–ORD, 09/03/26 – 09/13/26: From $303
    03

    Th

    • range$247-$399

    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)
    08/29/26 - 09/05/26

    Round trip

    Economy

    from
    $247Fare subject to changes
    Updated: 2 hours ago

    Orlando (MCO)to

    Chicago (ORD)
    09/05/26 - 09/12/26

    Round trip

    Economy

    from
    $247Fare subject to changes
    Updated: 2 hours ago

    Orlando (MCO)to

    Chicago (ORD)
    09/02/26 - 09/05/26

    Round trip

    Economy

    from
    $247Fare subject to changes
    Updated: 42 minutes ago

    Orlando (MCO)to

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

    Round trip

    Economy

    from
    $247Fare subject to changes
    Updated: 3 hours ago

    Orlando (MCO)to

    Chicago (ORD)
    09/02/26 - 09/06/26

    Round trip

    Economy

    from
    $247Fare subject to changes
    Updated: 9 minutes ago

    Orlando (MCO)to

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

    Round trip

    Economy

    from
    $247Fare subject to changes
    Updated: 3 hours ago

    Orlando (MCO)to

    Chicago (ORD)
    08/26/26 - 09/02/26

    Round trip

    Economy

    from
    $257Fare subject to changes
    Updated: 2 hours ago

    Orlando (MCO)to

    Chicago (ORD)
    08/27/26 - 09/03/26

    Round trip

    Economy

    from
    $257Fare 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.

    Finding cheap flights from Orlando to Chicago

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