American Airlines flights from Chicago to Portland, OR

Recent searches for flights from Chicago to Portland, OR

Sep 2026
From$383*
Updated: 14 hours ago
Round tripIEconomy
Oct 2026
From$269*
Updated: 14 hours ago
Round tripIEconomy
Nov 2026
From$269*
Updated: 14 hours ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $269
cmp-daily-histogram-bars-legend-max-price-aria-label $527
Displaying fares for September-2026
  • ORD–PDX, 09/15/26 – 09/23/26: From $497
    15

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    SEP

  • ORD–PDX, 09/16/26 – 09/23/26: From $497
    16

    We

  • ORD–PDX, 09/17/26 – 09/24/26: From $527
    17

    Th

  • ORD–PDX, 09/18/26 – 09/25/26: From $527
    18

    Fr

  • ORD–PDX, 09/19/26 – 09/26/26: From $497
    19

    Sa

  • ORD–PDX, 09/20/26 – 09/27/26: From $527
    20

    Su

  • ORD–PDX, 09/21/26 – 09/23/26: From $512
    21

    Mo

  • ORD–PDX, 09/22/26 – 09/29/26: From $497
    22

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  • ORD–PDX, 09/23/26 – 09/30/26: From $497
    23

    We

  • ORD–PDX, 09/24/26 – 10/01/26: From $527
    24

    Th

  • ORD–PDX, 09/25/26 – 10/02/26: From $527
    25

    Fr

  • ORD–PDX, 09/26/26 – 10/03/26: From $497
    26

    Sa

  • ORD–PDX, 09/27/26 – 10/04/26: From $527
    27

    Su

  • ORD–PDX, 09/28/26 – 10/05/26: From $418
    28

    Mo

  • ORD–PDX, 09/29/26 – 10/06/26: From $383
    29

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  • ORD–PDX, 09/30/26 – 10/07/26: From $383
    30

    We

  • ORD–PDX, 10/01/26 – 10/08/26: From $473
    01

    Th

    OCT

  • ORD–PDX, 10/02/26 – 10/09/26: From $438
    02

    Fr

  • ORD–PDX, 10/03/26 – 10/10/26: From $383
    03

    Sa

  • ORD–PDX, 10/04/26 – 10/11/26: From $502
    04

    Su

  • ORD–PDX, 10/05/26 – 10/12/26: From $309
    05

    Mo

  • ORD–PDX, 10/06/26 – 10/13/26: From $269
    06

    Tu

  • ORD–PDX, 10/07/26 – 10/14/26: From $269
    07

    We

  • ORD–PDX, 10/08/26 – 10/15/26: From $309
    08

    Th

  • ORD–PDX, 10/09/26 – 10/12/26: From $329
    09

    Fr

  • ORD–PDX, 10/10/26 – 10/17/26: From $269
    10

    Sa

  • ORD–PDX, 10/11/26 – 10/18/26: From $502
    11

    Su

  • ORD–PDX, 10/12/26 – 10/19/26: From $364
    12

    Mo

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

    Tu

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

    We

    • range$269-$527

    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, OR flights

    $
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    Chicago (ORD)to

    Portland, OR (PDX)
    10/21/26 - 10/28/26

    Round trip

    Economy

    from
    $269Fare subject to changes
    Updated: 14 hours ago

    Chicago (ORD)to

    Portland, OR (PDX)
    10/24/26 - 10/31/26

    Round trip

    Economy

    from
    $269Fare subject to changes
    Updated: 14 hours ago

    Chicago (ORD)to

    Portland, OR (PDX)
    10/27/26 - 11/03/26

    Round trip

    Economy

    from
    $269Fare subject to changes
    Updated: 14 hours ago

    Chicago (ORD)to

    Portland, OR (PDX)
    10/28/26 - 11/04/26

    Round trip

    Economy

    from
    $269Fare subject to changes
    Updated: 14 hours ago

    Chicago (ORD)to

    Portland, OR (PDX)
    10/07/26 - 10/14/26

    Round trip

    Economy

    from
    $269Fare subject to changes
    Updated: 14 hours ago

    Chicago (ORD)to

    Portland, OR (PDX)
    12/01/26 - 12/08/26

    Round trip

    Economy

    from
    $269Fare subject to changes
    Updated: 14 hours ago

    Chicago (ORD)to

    Portland, OR (PDX)
    12/05/26 - 12/12/26

    Round trip

    Economy

    from
    $269Fare subject to changes
    Updated: 14 hours ago

    Chicago (ORD)to

    Portland, OR (PDX)
    12/08/26 - 12/15/26

    Round trip

    Economy

    from
    $269Fare 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.

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