Southwest® flights from Oklahoma City to Chicago (Midway) from $119

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Low fares from Oklahoma City to Chicago (Midway)

$

Oklahoma City (OKC)to

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

One-way

Basic

From
$119
Seen: 12 hrs ago

Oklahoma City (OKC)to

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

One-way

Basic

From
$119
Seen: 11 hrs ago

Oklahoma City (OKC)to

Chicago (Midway) (MDW)
Depart: 09/16/2026

One-way

Basic

From
$119
Seen: 20 hrs ago

Oklahoma City (OKC)to

Chicago (Midway) (MDW)
Depart: 09/08/2026

One-way

Basic

From
$119
Seen: 8 hrs ago

Oklahoma City (OKC)to

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

One-way

Basic

From
$119
Seen: 8 hrs ago

Oklahoma City (OKC)to

Chicago (Midway) (MDW)
Depart: 11/07/2026

One-way

Basic

From
$119
Seen: 2 hrs ago

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Explore flights from Oklahoma City to Chicago (Midway)

Aug 2026
From$233*
Seen: 6 hrs ago
One Way/Basic
Sep 2026
From$119*
Seen: 2 hrs ago
One Way/Basic
Oct 2026
From$119*
Seen: 22 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $119
cmp-daily-histogram-bars-legend-max-price-aria-label $261
Displaying fares for August-2026
  • OKC–MDW, 08/19/2026: From $233
    19

    Wed

    AUG

  • OKC–MDW, 08/20/2026: From $261
    20

    Thu

  • OKC–MDW, 08/21/2026: From $261
    21

    Fri

  • OKC–MDW, 08/22/2026: From $233
    22

    Sat

  • OKC–MDW, 08/23/2026: From $261
    23

    Sun

  • OKC–MDW, 08/24/2026: From $261
    24

    Mon

  • OKC–MDW: cmp-view-offers-disclaimer. Find Offers
    25

    Tue

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

    Wed

  • OKC–MDW, 08/27/2026: From $261
    27

    Thu

  • OKC–MDW, 08/28/2026: From $261
    28

    Fri

  • OKC–MDW, 08/29/2026: From $233
    29

    Sat

  • OKC–MDW: cmp-view-offers-disclaimer. Find Offers
    30

    Sun

  • OKC–MDW: cmp-view-offers-disclaimer. Find Offers
    31

    Mon

  • OKC–MDW, 09/01/2026: From $233
    01

    Tue

    SEP

  • OKC–MDW, 09/02/2026: From $233
    02

    Wed

  • OKC–MDW: cmp-view-offers-disclaimer. Find Offers
    03

    Thu

  • OKC–MDW, 09/04/2026: From $244
    04

    Fri

  • OKC–MDW, 09/05/2026: From $185
    05

    Sat

  • OKC–MDW, 09/06/2026: From $185
    06

    Sun

  • OKC–MDW, 09/07/2026: From $234
    07

    Mon

  • OKC–MDW, 09/08/2026: From $119
    08

    Tue

  • OKC–MDW, 09/09/2026: From $129
    09

    Wed

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

    Thu

  • OKC–MDW: cmp-view-offers-disclaimer. Find Offers
    11

    Fri

  • OKC–MDW, 09/12/2026: From $119
    12

    Sat

  • OKC–MDW: cmp-view-offers-disclaimer. Find Offers
    13

    Sun

  • OKC–MDW, 09/14/2026: From $119
    14

    Mon

  • OKC–MDW: cmp-view-offers-disclaimer. Find Offers
    15

    Tue

  • OKC–MDW, 09/16/2026: From $119
    16

    Wed

  • OKC–MDW, 09/17/2026: From $182
    17

    Thu

  • OKC–MDW: cmp-view-offers-disclaimer. Find Offers
    18

    Fri

    • Range$119-$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:
    Chicago Midway International Airport
    Average flight time:
    1 hour 55 minutes
    Distance:
    691 miles

    Route Information

    151† Weekly flights
    • 1‡ Nonstop flight per day Monday through Friday
    • 1‡ Nonstop flight on Saturday
    • 2‡ Nonstop flights on Sunday

    † 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

    The average flight time from Oklahoma City to Chicago (Midway) is 1 hour 55 minutes.
    There are 151 weekly flights from Oklahoma City to Chicago (Midway) on Southwest Airlines.
    Yes, Southwest flies nonstop from Oklahoma City to Chicago (Midway) once per day from Monday through Friday.
    Yes, Southwest flies nonstop from Oklahoma City to Chicago (Midway) once per day on Saturdays and 2 times per day on Sundays.
    To find the lowest fares by day and time to fly Oklahoma City to Chicago (Midway) with Southwest, check out our Low Fare Calendar.
    You can rent a car at Chicago Midway International Airport book yours with your flight.
    Yes! Flights from Oklahoma City to Chicago (Midway)—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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