American Airlines flights from Stillwater to Chicago

Recent searches for flights from Stillwater to Chicago

Sep 2026
From$454*
Updated: 11 hours ago
Round tripIEconomy
Oct 2026
From$443*
Updated: 11 hours ago
Round tripIEconomy
Nov 2026
From$443*
Updated: 11 hours ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $454
cmp-daily-histogram-bars-legend-max-price-aria-label $756
Displaying fares for September-2026
  • SWO–ORD, 09/04/26 – 09/11/26: From $610
    04

    Fr

    SEP

  • SWO–ORD, 09/05/26 – 09/12/26: From $553
    05

    Sa

  • SWO–ORD, 09/06/26 – 09/13/26: From $610
    06

    Su

  • SWO–ORD, 09/07/26 – 09/14/26: From $561
    07

    Mo

  • SWO–ORD, 09/08/26 – 09/15/26: From $553
    08

    Tu

  • SWO–ORD, 09/09/26 – 09/16/26: From $553
    09

    We

  • SWO–ORD, 09/10/26 – 09/17/26: From $707
    10

    Th

  • SWO–ORD, 09/11/26 – 09/18/26: From $559
    11

    Fr

  • SWO–ORD, 09/12/26 – 09/19/26: From $530
    12

    Sa

  • SWO–ORD, 09/13/26 – 09/20/26: From $652
    13

    Su

  • SWO–ORD, 09/14/26 – 09/21/26: From $559
    14

    Mo

  • SWO–ORD, 09/15/26 – 09/22/26: From $530
    15

    Tu

  • SWO–ORD, 09/16/26 – 09/23/26: From $530
    16

    We

  • SWO–ORD, 09/17/26 – 09/24/26: From $486
    17

    Th

  • SWO–ORD, 09/18/26 – 09/25/26: From $486
    18

    Fr

  • SWO–ORD, 09/19/26 – 09/26/26: From $486
    19

    Sa

  • SWO–ORD, 09/20/26 – 09/27/26: From $756
    20

    Su

  • SWO–ORD, 09/21/26 – 09/28/26: From $486
    21

    Mo

  • SWO–ORD, 09/22/26 – 09/29/26: From $486
    22

    Tu

  • SWO–ORD, 09/23/26 – 09/30/26: From $486
    23

    We

  • SWO–ORD, 09/24/26 – 10/01/26: From $465
    24

    Th

  • SWO–ORD, 09/25/26 – 10/02/26: From $465
    25

    Fr

  • SWO–ORD, 09/26/26 – 10/03/26: From $454
    26

    Sa

  • SWO–ORD, 09/27/26 – 10/04/26: From $454
    27

    Su

  • SWO–ORD, 09/28/26 – 10/05/26: From $454
    28

    Mo

  • SWO–ORD, 09/29/26 – 10/06/26: From $454
    29

    Tu

  • SWO–ORD, 09/30/26 – 10/07/26: From $454
    30

    We

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

    Th

    OCT

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

    Fr

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

    Sa

    • range$454-$756

    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 Stillwater to Chicago flights

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    Stillwater (SWO)to

    Chicago (ORD)
    10/06/26 - 10/13/26

    Round trip

    Economy

    from
    $443Fare subject to changes
    Updated: 11 hours ago

    Stillwater (SWO)to

    Chicago (ORD)
    10/10/26 - 10/17/26

    Round trip

    Economy

    from
    $443Fare subject to changes
    Updated: 11 hours ago

    Stillwater (SWO)to

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

    Round trip

    Economy

    from
    $443Fare subject to changes
    Updated: 11 hours ago

    Stillwater (SWO)to

    Chicago (ORD)
    10/16/26 - 10/23/26

    Round trip

    Economy

    from
    $443Fare subject to changes
    Updated: 11 hours ago

    Stillwater (SWO)to

    Chicago (ORD)
    10/17/26 - 10/24/26

    Round trip

    Economy

    from
    $443Fare subject to changes
    Updated: 11 hours ago

    Stillwater (SWO)to

    Chicago (ORD)
    10/19/26 - 10/26/26

    Round trip

    Economy

    from
    $443Fare subject to changes
    Updated: 11 hours ago

    Stillwater (SWO)to

    Chicago (ORD)
    10/27/26 - 11/03/26

    Round trip

    Economy

    from
    $443Fare subject to changes
    Updated: 11 hours ago

    Stillwater (SWO)to

    Chicago (ORD)
    11/10/26 - 11/17/26

    Round trip

    Economy

    from
    $443Fare subject to changes
    Updated: 11 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 Stillwater to Chicago

    Looking for lower fares on your trip from Stillwater 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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    American Airlines flights from Stillwater to Chicago