American Airlines flights from Chicago to Portland, ME

Recent searches for flights from Chicago to Portland, ME

Sep 2026
From$411*
Updated: 14 hours ago
Round tripIEconomy
Oct 2026
From$357*
Updated: 2 hours ago
Round tripIEconomy
Nov 2026
From$351*
Updated: 8 hours ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $384
cmp-daily-histogram-bars-legend-max-price-aria-label $775
Displaying fares for September-2026
  • ORD–PWM, 09/13/26 – 09/20/26: From $517
    13

    Su

    SEP

  • ORD–PWM, 09/14/26 – 09/21/26: From $517
    14

    Mo

  • ORD–PWM, 09/15/26 – 09/22/26: From $427
    15

    Tu

  • ORD–PWM, 09/16/26 – 09/23/26: From $417
    16

    We

  • ORD–PWM, 09/17/26 – 09/24/26: From $517
    17

    Th

  • ORD–PWM, 09/18/26 – 09/25/26: From $517
    18

    Fr

  • ORD–PWM, 09/19/26 – 09/26/26: From $417
    19

    Sa

  • ORD–PWM, 09/20/26 – 09/27/26: From $521
    20

    Su

  • ORD–PWM, 09/21/26 – 09/28/26: From $517
    21

    Mo

  • ORD–PWM, 09/22/26 – 09/29/26: From $417
    22

    Tu

  • ORD–PWM, 09/23/26 – 09/30/26: From $427
    23

    We

  • ORD–PWM, 09/24/26 – 10/01/26: From $517
    24

    Th

  • ORD–PWM, 09/25/26 – 10/02/26: From $517
    25

    Fr

  • ORD–PWM, 09/26/26 – 10/03/26: From $411
    26

    Sa

  • ORD–PWM, 09/27/26 – 10/04/26: From $511
    27

    Su

  • ORD–PWM, 09/28/26 – 10/05/26: From $527
    28

    Mo

  • ORD–PWM, 09/29/26 – 10/06/26: From $417
    29

    Tu

  • ORD–PWM, 09/30/26 – 10/07/26: From $417
    30

    We

  • ORD–PWM, 10/01/26 – 10/08/26: From $527
    01

    Th

    OCT

  • ORD–PWM, 10/02/26 – 10/09/26: From $546
    02

    Fr

  • ORD–PWM, 10/03/26 – 10/10/26: From $427
    03

    Sa

  • ORD–PWM, 10/04/26 – 10/11/26: From $527
    04

    Su

  • ORD–PWM, 10/05/26 – 10/12/26: From $775
    05

    Mo

  • ORD–PWM, 10/06/26 – 10/13/26: From $459
    06

    Tu

  • ORD–PWM, 10/07/26 – 10/14/26: From $397
    07

    We

  • ORD–PWM, 10/08/26 – 10/15/26: From $484
    08

    Th

  • ORD–PWM, 10/09/26 – 10/16/26: From $484
    09

    Fr

  • ORD–PWM, 10/10/26 – 10/17/26: From $384
    10

    Sa

  • ORD–PWM: cmp-view-offers-disclaimer. Find Offers
    11

    Su

  • ORD–PWM: cmp-view-offers-disclaimer. Find Offers
    12

    Mo

    • range$384-$775

    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 Chicago to Portland, ME flights

    $
    keyboard_arrow_down

    Chicago (ORD)to

    Portland, ME (PWM)
    11/10/26 - 11/17/26

    Round trip

    Economy

    from
    $351Fare subject to changes
    Updated: 8 hours ago

    Chicago (ORD)to

    Portland, ME (PWM)
    10/17/26 - 10/24/26

    Round trip

    Economy

    from
    $357Fare subject to changes
    Updated: 2 hours ago

    Chicago (ORD)to

    Portland, ME (PWM)
    10/24/26 - 10/31/26

    Round trip

    Economy

    from
    $357Fare subject to changes
    Updated: 2 hours ago

    Chicago (ORD)to

    Portland, ME (PWM)
    12/05/26 - 12/12/26

    Round trip

    Economy

    from
    $357Fare subject to changes
    Updated: 2 hours ago

    Chicago (ORD)to

    Portland, ME (PWM)
    12/08/26 - 12/15/26

    Round trip

    Economy

    from
    $357Fare subject to changes
    Updated: 2 hours ago

    Chicago (ORD)to

    Portland, ME (PWM)
    11/03/26 - 11/10/26

    Round trip

    Economy

    from
    $357Fare subject to changes
    Updated: 2 hours ago

    Chicago (ORD)to

    Portland, ME (PWM)
    11/14/26 - 11/21/26

    Round trip

    Economy

    from
    $357Fare subject to changes
    Updated: 2 hours ago

    Chicago (ORD)to

    Portland, ME (PWM)
    10/20/26 - 10/27/26

    Round trip

    Economy

    from
    $357Fare 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 Chicago to Portland, ME

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

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    • 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 Chicago to Portland, ME