American Airlines flights from Portland, OR to Chicago

Recent searches for flights from Portland, OR to Chicago

Sep 2026
From$357*
Updated: 5 hours ago
Round tripIEconomy
Oct 2026
From$357*
Updated: 5 hours ago
Round tripIEconomy
Nov 2026
From$357*
Updated: 5 hours ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $357
cmp-daily-histogram-bars-legend-max-price-aria-label $507
Displaying fares for September-2026
  • PDX–ORD, 09/06/26 – 09/13/26: From $507
    06

    Su

    SEP

  • PDX–ORD, 09/07/26 – 09/14/26: From $507
    07

    Mo

  • PDX–ORD, 09/08/26 – 09/15/26: From $477
    08

    Tu

  • PDX–ORD, 09/09/26 – 09/16/26: From $477
    09

    We

  • PDX–ORD, 09/10/26 – 09/17/26: From $507
    10

    Th

  • PDX–ORD, 09/11/26 – 09/18/26: From $507
    11

    Fr

  • PDX–ORD, 09/12/26 – 09/19/26: From $477
    12

    Sa

  • PDX–ORD, 09/13/26 – 09/20/26: From $507
    13

    Su

  • PDX–ORD, 09/14/26 – 09/21/26: From $507
    14

    Mo

  • PDX–ORD, 09/15/26 – 09/22/26: From $477
    15

    Tu

  • PDX–ORD, 09/16/26 – 09/23/26: From $477
    16

    We

  • PDX–ORD, 09/17/26 – 09/24/26: From $507
    17

    Th

  • PDX–ORD, 09/18/26 – 09/25/26: From $507
    18

    Fr

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

    Sa

  • PDX–ORD, 09/20/26 – 09/27/26: From $482
    20

    Su

  • PDX–ORD, 09/21/26 – 09/28/26: From $432
    21

    Mo

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

    Tu

  • PDX–ORD, 09/23/26 – 09/30/26: From $417
    23

    We

  • PDX–ORD, 09/24/26 – 10/01/26: From $432
    24

    Th

  • PDX–ORD, 09/25/26 – 10/02/26: From $451
    25

    Fr

  • PDX–ORD, 09/26/26 – 10/03/26: From $357
    26

    Sa

  • PDX–ORD, 09/27/26 – 10/04/26: From $457
    27

    Su

  • PDX–ORD, 09/28/26 – 10/05/26: From $357
    28

    Mo

  • PDX–ORD, 09/29/26 – 10/06/26: From $357
    29

    Tu

  • PDX–ORD, 09/30/26 – 10/07/26: From $357
    30

    We

  • PDX–ORD, 10/01/26 – 10/08/26: From $357
    01

    Th

    OCT

  • PDX–ORD, 10/02/26 – 10/09/26: From $395
    02

    Fr

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

    Sa

  • PDX–ORD: cmp-view-offers-disclaimer. Find Offers
    04

    Su

  • PDX–ORD, 10/05/26 – 10/07/26: From $357
    05

    Mo

    • range$357-$507

    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, OR to Chicago flights

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    Portland, OR (PDX)to

    Chicago (ORD)
    10/01/26 - 10/08/26

    Round trip

    Economy

    from
    $357Fare subject to changes
    Updated: 5 hours ago

    Portland, OR (PDX)to

    Chicago (ORD)
    10/14/26 - 10/21/26

    Round trip

    Economy

    from
    $357Fare subject to changes
    Updated: 5 hours ago

    Portland, OR (PDX)to

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

    Round trip

    Economy

    from
    $357Fare subject to changes
    Updated: 5 hours ago

    Portland, OR (PDX)to

    Chicago (ORD)
    10/21/26 - 10/28/26

    Round trip

    Economy

    from
    $357Fare subject to changes
    Updated: 5 hours ago

    Portland, OR (PDX)to

    Chicago (ORD)
    10/22/26 - 10/29/26

    Round trip

    Economy

    from
    $357Fare subject to changes
    Updated: 5 hours ago

    Portland, OR (PDX)to

    Chicago (ORD)
    09/28/26 - 10/05/26

    Round trip

    Economy

    from
    $357Fare subject to changes
    Updated: 5 hours ago

    Portland, OR (PDX)to

    Chicago (ORD)
    11/05/26 - 11/12/26

    Round trip

    Economy

    from
    $357Fare subject to changes
    Updated: 5 hours ago

    Portland, OR (PDX)to

    Chicago (ORD)
    11/07/26 - 11/14/26

    Round trip

    Economy

    from
    $357Fare subject to changes
    Updated: 5 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, OR to Chicago

    Looking for lower fares on your trip from Portland, OR 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

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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.
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    American Airlines flights from Portland, OR to Chicago