Alaska Airlines Flights from Portland to Chicago

Lowest fares from Portland to Chicago

Aug 2026
From$179*
Seen: 20 hours ago
Flight Type One Way|Saver
Sep 2026
From$179*
Seen: 20 hours ago
Flight Type One Way|Saver
Oct 2026
From$179*
Seen: 20 hours ago
Flight Type One Way|Saver
cmp-daily-histogram-bars-legend-min-price-aria-label $179
cmp-daily-histogram-bars-legend-max-price-aria-label $306
Displaying fares for August-2026
  • PDX–ORD, Aug 9, 2026: From $306
    09

    Su

    AUG

  • PDX–ORD, Aug 10, 2026: From $242
    10

    Mo

  • PDX–ORD, Aug 11, 2026: From $219
    11

    Tu

  • PDX–ORD, Aug 12, 2026: From $219
    12

    We

  • PDX–ORD, Aug 13, 2026: From $261
    13

    Th

  • PDX–ORD, Aug 14, 2026: From $271
    14

    Fr

  • PDX–ORD, Aug 15, 2026: From $306
    15

    Sa

  • PDX–ORD, Aug 16, 2026: From $242
    16

    Su

  • PDX–ORD, Aug 17, 2026: From $242
    17

    Mo

  • PDX–ORD, Aug 18, 2026: From $225
    18

    Tu

  • PDX–ORD, Aug 19, 2026: From $229
    19

    We

  • PDX–ORD, Aug 20, 2026: From $252
    20

    Th

  • PDX–ORD, Aug 21, 2026: From $252
    21

    Fr

  • PDX–ORD, Aug 22, 2026: From $219
    22

    Sa

  • PDX–ORD, Aug 23, 2026: From $261
    23

    Su

  • PDX–ORD, Aug 24, 2026: From $252
    24

    Mo

  • PDX–ORD, Aug 25, 2026: From $229
    25

    Tu

  • PDX–ORD, Aug 26, 2026: From $229
    26

    We

  • PDX–ORD, Aug 27, 2026: From $252
    27

    Th

  • PDX–ORD, Aug 28, 2026: From $242
    28

    Fr

  • PDX–ORD, Aug 29, 2026: From $179
    29

    Sa

  • PDX–ORD, Aug 30, 2026: From $179
    30

    Su

  • PDX–ORD, Aug 31, 2026: From $179
    31

    Mo

  • PDX–ORD, Sep 1, 2026: From $179
    01

    Tu

    SEP

  • PDX–ORD, Sep 2, 2026: From $187
    02

    We

  • PDX–ORD, Sep 3, 2026: From $229
    03

    Th

  • PDX–ORD, Sep 4, 2026: From $189
    04

    Fr

  • PDX–ORD, Sep 5, 2026: From $179
    05

    Sa

  • PDX–ORD, Sep 6, 2026: From $179
    06

    Su

  • PDX–ORD, Sep 7, 2026: From $219
    07

    Mo

  • PDX–ORD, Sep 8, 2026: From $189
    08

    Tu

    • Range$179-$306

    *Displayed prices have been available within the past 24 hours and may not be available at the time of booking. Fares listed may be Saver fares, which is our most restrictive fare option and subject to additional restrictions. For roundtrip journeys, the price displayed—available within the past 24 hours—is the aggregate of the lowest available fare each way. Additional baggage charges and fees for optional products and services may apply. Other terms and conditions may apply.

    One-way low-fare flights Portland to Chicago.*

    $
    keyboard_arrow_down
    One-way low-fare flights Portland to Chicago.*
    From
    To
    Fare Type
    Dates
    Price
    Portland (PDX)Chicago (ORD)One-way
    |
    Saver    		Depart: Sep 1, 2026

    From

    $179

    Seen: 20 hours ago

    Portland (PDX)Chicago (ORD)One-way
    |
    Saver    		Depart: Sep 5, 2026

    From

    $179

    Seen: 20 hours ago

    Portland (PDX)Chicago (ORD)One-way
    |
    Saver    		Depart: Sep 26, 2026

    From

    $179

    Seen: 20 hours ago

    Portland (PDX)Chicago (ORD)One-way
    |
    Saver    		Depart: Sep 28, 2026

    From

    $179

    Seen: 20 hours ago

    Portland (PDX)Chicago (ORD)One-way
    |
    Saver    		Depart: Oct 31, 2026

    From

    $179

    Seen: 20 hours ago

    Portland (PDX)Chicago (ORD)One-way
    |
    Saver    		Depart: Nov 3, 2026

    From

    $179

    Seen: 20 hours ago

    Portland (PDX)Chicago (ORD)One-way
    |
    Saver    		Depart: Nov 13, 2026

    From

    $179

    Seen: 20 hours ago

    Portland (PDX)Chicago (ORD)One-way
    |
    Saver    		Depart: Nov 15, 2026

    From

    $179

    Seen: 20 hours ago

    *Displayed prices have been available within the past 24 hours and may not be available at the time of booking. Fares listed may be Saver fares, which is our most restrictive fare option and subject to additional restrictions. For roundtrip journeys, the price displayed—available within the past 24 hours—is the aggregate of the lowest available fare each way. Additional baggage charges and fees for optional products and services may apply. Other terms and conditions may apply.

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