American Airlines flights from Portland, ME to Chicago

Recent searches for flights from Portland, ME to Chicago

Aug 2026
From$262*
Updated: 2 hours ago
Round tripIEconomy
Sep 2026
From$262*
Updated: 2 hours ago
Round tripIEconomy
Oct 2026
From$262*
Updated: 10 hours ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $262
cmp-daily-histogram-bars-legend-max-price-aria-label $777
Displaying fares for August-2026
  • PWM–ORD, 08/05/26 – 08/12/26: From $377
    05

    We

    AUG

  • PWM–ORD, 08/06/26 – 08/18/26: From $427
    06

    Th

  • PWM–ORD, 08/07/26 – 08/14/26: From $487
    07

    Fr

  • PWM–ORD, 08/08/26 – 08/15/26: From $387
    08

    Sa

  • PWM–ORD, 08/09/26 – 08/16/26: From $621
    09

    Su

  • PWM–ORD, 08/10/26 – 08/17/26: From $777
    10

    Mo

  • PWM–ORD, 08/11/26 – 08/18/26: From $387
    11

    Tu

  • PWM–ORD, 08/12/26 – 08/19/26: From $387
    12

    We

  • PWM–ORD, 08/13/26 – 08/20/26: From $487
    13

    Th

  • PWM–ORD, 08/14/26 – 08/15/26: From $427
    14

    Fr

  • PWM–ORD, 08/15/26 – 08/22/26: From $377
    15

    Sa

  • PWM–ORD, 08/16/26 – 08/23/26: From $487
    16

    Su

  • PWM–ORD, 08/17/26 – 08/24/26: From $487
    17

    Mo

  • PWM–ORD, 08/18/26 – 08/25/26: From $333
    18

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  • PWM–ORD, 08/19/26 – 08/26/26: From $333
    19

    We

  • PWM–ORD, 08/20/26 – 08/27/26: From $383
    20

    Th

  • PWM–ORD, 08/21/26 – 08/28/26: From $416
    21

    Fr

  • PWM–ORD, 08/22/26 – 08/29/26: From $333
    22

    Sa

  • PWM–ORD, 08/23/26 – 08/30/26: From $487
    23

    Su

  • PWM–ORD, 08/24/26 – 08/31/26: From $383
    24

    Mo

  • PWM–ORD, 08/25/26 – 09/01/26: From $289
    25

    Tu

  • PWM–ORD, 08/26/26 – 09/02/26: From $289
    26

    We

  • PWM–ORD, 08/27/26 – 09/03/26: From $375
    27

    Th

  • PWM–ORD, 08/28/26 – 08/31/26: From $322
    28

    Fr

  • PWM–ORD, 08/29/26 – 09/05/26: From $262
    29

    Sa

  • PWM–ORD, 08/30/26 – 09/06/26: From $356
    30

    Su

  • PWM–ORD, 08/31/26 – 09/07/26: From $289
    31

    Mo

  • PWM–ORD: cmp-view-offers-disclaimer. Find Offers
    01

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    SEP

  • PWM–ORD: cmp-view-offers-disclaimer. Find Offers
    02

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  • PWM–ORD: cmp-view-offers-disclaimer. Find Offers
    03

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  • PWM–ORD, 09/04/26 – 09/11/26: From $295
    04

    Fr

    • range$262-$777

    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 Portland, ME to Chicago flights

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    keyboard_arrow_down

    Portland, ME (PWM)to

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

    Round trip

    Economy

    from
    $262Fare subject to changes
    Updated: 2 hours ago

    Portland, ME (PWM)to

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

    Round trip

    Economy

    from
    $262Fare subject to changes
    Updated: 2 hours ago

    Portland, ME (PWM)to

    Chicago (ORD)
    10/30/26 - 11/07/26

    Round trip

    Economy

    from
    $262Fare subject to changes
    Updated: 10 hours ago

    Portland, ME (PWM)to

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

    Round trip

    Economy

    from
    $289Fare subject to changes
    Updated: 2 hours ago

    Portland, ME (PWM)to

    Chicago (ORD)
    10/29/26 - 11/05/26

    Round trip

    Economy

    from
    $289Fare subject to changes
    Updated: 2 hours ago

    Portland, ME (PWM)to

    Chicago (ORD)
    09/14/26 - 09/21/26

    Round trip

    Economy

    from
    $289Fare subject to changes
    Updated: 2 hours ago

    Portland, ME (PWM)to

    Chicago (ORD)
    09/15/26 - 09/22/26

    Round trip

    Economy

    from
    $289Fare subject to changes
    Updated: 2 hours ago

    Portland, ME (PWM)to

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

    Round trip

    Economy

    from
    $289Fare 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 Portland, ME to Chicago

    Looking for lower fares on your trip from Portland, ME 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 Portland, ME to Chicago