Southwest® flights from Oklahoma City to Chicago (O'Hare)

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Low fares from Oklahoma City to Chicago (O'Hare)

$

Oklahoma City (OKC)to

Chicago (Midway) (MDW)
Depart: 10/30/2026

One-way

Basic

From
$119
Seen: 9 hrs ago

Oklahoma City (OKC)to

Chicago (Midway) (MDW)
Depart: 09/05/2026

One-way

Basic

From
$119
Seen: 3 hrs ago

Oklahoma City (OKC)to

Chicago (Midway) (MDW)
Depart: 09/26/2026

One-way

Basic

From
$131
Seen: 19 hrs ago

Oklahoma City (OKC)to

Chicago (Midway) (MDW)
Depart: 09/21/2026

One-way

Basic

From
$131
Seen: 21 hrs ago

Oklahoma City (OKC)to

Chicago (Midway) (MDW)
Depart: 09/19/2026

One-way

Basic

From
$131
Seen: 1 hour ago

Oklahoma City (OKC)to

Chicago (Midway) (MDW)
Depart: 08/25/2026

One-way

Basic

From
$131
Seen: 22 hrs ago

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Explore flights from Oklahoma City to Chicago (O'Hare)

Aug 2026
From$131*
Seen: 6 hrs ago
One Way/Basic
Sep 2026
From$119*
Seen: 3 hrs ago
One Way/Basic
Oct 2026
From$119*
Seen: 9 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $131
cmp-daily-histogram-bars-legend-max-price-aria-label $261
Displaying fares for August-2026
  • OKC–MDW, 08/05/2026: From $233
    05

    Wed

    AUG

  • OKC–MDW, 08/06/2026: From $261
    06

    Thu

  • OKC–MDW: cmp-view-offers-disclaimer. Find Offers
    07

    Fri

  • OKC–MDW, 08/08/2026: From $233
    08

    Sat

  • OKC–MDW, 08/09/2026: From $261
    09

    Sun

  • OKC–MDW: cmp-view-offers-disclaimer. Find Offers
    10

    Mon

  • OKC–MDW, 08/11/2026: From $233
    11

    Tue

  • OKC–MDW: cmp-view-offers-disclaimer. Find Offers
    12

    Wed

  • OKC–MDW, 08/13/2026: From $261
    13

    Thu

  • OKC–MDW, 08/14/2026: From $261
    14

    Fri

  • OKC–MDW, 08/15/2026: From $233
    15

    Sat

  • OKC–MDW, 08/16/2026: From $261
    16

    Sun

  • OKC–MDW, 08/17/2026: From $261
    17

    Mon

  • OKC–MDW, 08/18/2026: From $233
    18

    Tue

  • OKC–MDW: cmp-view-offers-disclaimer. Find Offers
    19

    Wed

  • OKC–MDW: cmp-view-offers-disclaimer. Find Offers
    20

    Thu

  • OKC–MDW, 08/21/2026: From $234
    21

    Fri

  • OKC–MDW: cmp-view-offers-disclaimer. Find Offers
    22

    Sat

  • OKC–MDW, 08/23/2026: From $234
    23

    Sun

  • OKC–MDW, 08/24/2026: From $234
    24

    Mon

  • OKC–MDW, 08/25/2026: From $131
    25

    Tue

  • OKC–MDW: cmp-view-offers-disclaimer. Find Offers
    26

    Wed

  • OKC–MDW, 08/27/2026: From $141
    27

    Thu

  • OKC–MDW: cmp-view-offers-disclaimer. Find Offers
    28

    Fri

  • OKC–MDW: cmp-view-offers-disclaimer. Find Offers
    29

    Sat

  • OKC–MDW, 08/30/2026: From $213
    30

    Sun

  • OKC–MDW, 08/31/2026: From $131
    31

    Mon

  • OKC–MDW, 09/01/2026: From $131
    01

    Tue

    SEP

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    02

    Wed

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    03

    Thu

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    04

    Fri

    • Range$131-$261

    *Fares displayed have been collected within the last 24 hours and may no longer be available at time of booking. Additional fees and charges for optional products and services may apply. Modifying this information may result in a different fare. To find the most updated fare, please visit Southwest.com. Fares listed are Basic, which are subject to additional terms and conditions.

    Flight Details

    Departing from:
    Will Rogers Airport
    Arriving at:
    O'Hare International Airport
    Distance:
    693 miles

    Route Information

    73† Weekly flights

    † Weekly flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025. Note: route may not operate every day of the week.

    ‡ Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025.

    Questions we hear the most

    There are 73 weekly flights from Oklahoma City to Chicago (O'Hare) on Southwest Airlines.
    To find the lowest fares by day and time to fly Oklahoma City to Chicago (O'Hare) with Southwest, check out our Low Fare Calendar.
    You can rent a car at O'Hare International Airport book yours with your flight.
    Yes! Flights from Oklahoma City to Chicago (O'Hare)—or from here or there to anywhere—can be changed with no change fees. Fare difference may apply.
    Check the status of your upcoming Southwest flight.
    Check out the Southwest Airlines® Help Center for answers about everything Southwest.

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