Southwest® flights from Oklahoma City to Chicago-Midway from $135

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Low fares from Oklahoma City to Chicago-Midway

$

Oklahoma City (OKC)to

Chicago-Midway (MDW)
Depart: 12/09/2026

One-way

Basic

From
$135
Seen: 13 hrs ago

Oklahoma City (OKC)to

Chicago-Midway (MDW)
Depart: 12/16/2026

One-way

Basic

From
$135
Seen: 3 hrs ago

Oklahoma City (OKC)to

Chicago-Midway (MDW)
Depart: 12/23/2026

One-way

Basic

From
$135
Seen: 34 minutes ago

Oklahoma City (OKC)to

Chicago-Midway (MDW)
Depart: 11/26/2026

One-way

Basic

From
$145
Seen: 13 hrs ago

Oklahoma City (OKC)to

Chicago-Midway (MDW)
Depart: 11/30/2026

One-way

Basic

From
$163
Seen: 6 hrs ago

Oklahoma City (OKC)to

Chicago-Midway (MDW)
Depart: 12/23/2026

One-way

Choice

From
$181
Seen: 34 minutes ago

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Explore flights from Oklahoma City to Chicago-Midway

Oct 2026
From$263*
Seen: 11 hrs ago
One Way/Basic
Nov 2026
From$145*
Seen: 13 hrs ago
One Way/Basic
Dec 2026
From$135*
Seen: 13 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $215
cmp-daily-histogram-bars-legend-max-price-aria-label $291
Displaying fares for October-2026
  • OKC–MDW, 10/19/2026: From $291
    19

    Mon

    OCT

  • OKC–MDW, 10/20/2026: From $263
    20

    Tue

  • OKC–MDW, 10/21/2026: From $263
    21

    Wed

  • OKC–MDW, 10/22/2026: From $291
    22

    Thu

  • OKC–MDW: cmp-view-offers-disclaimer. Find Offers
    23

    Fri

  • OKC–MDW: cmp-view-offers-disclaimer. Find Offers
    24

    Sat

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

    Sun

  • OKC–MDW, 10/26/2026: From $291
    26

    Mon

  • OKC–MDW, 10/27/2026: From $263
    27

    Tue

  • OKC–MDW, 10/28/2026: From $263
    28

    Wed

  • OKC–MDW, 10/29/2026: From $291
    29

    Thu

  • OKC–MDW, 10/30/2026: From $291
    30

    Fri

  • OKC–MDW, 10/31/2026: From $263
    31

    Sat

  • OKC–MDW, 11/01/2026: From $264
    01

    Sun

    NOV

  • OKC–MDW, 11/02/2026: From $264
    02

    Mon

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

    Tue

  • OKC–MDW, 11/04/2026: From $263
    04

    Wed

  • OKC–MDW: cmp-view-offers-disclaimer. Find Offers
    05

    Thu

  • OKC–MDW, 11/06/2026: From $264
    06

    Fri

  • OKC–MDW, 11/07/2026: From $263
    07

    Sat

  • OKC–MDW: cmp-view-offers-disclaimer. Find Offers
    08

    Sun

  • OKC–MDW: cmp-view-offers-disclaimer. Find Offers
    09

    Mon

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

    Tue

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

    Wed

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

    Thu

  • OKC–MDW, 11/13/2026: From $243
    13

    Fri

  • OKC–MDW: cmp-view-offers-disclaimer. Find Offers
    14

    Sat

  • OKC–MDW, 11/15/2026: From $243
    15

    Sun

  • OKC–MDW, 11/16/2026: From $243
    16

    Mon

  • OKC–MDW, 11/17/2026: From $215
    17

    Tue

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

    Wed

    • Range$215-$291

    *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

    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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