Southwest® flights from Oklahoma City to Chicago-Midway from $163

Promo Code

Low fares from Oklahoma City to Chicago-Midway

$

Oklahoma City (OKC)to

Chicago-Midway (MDW)
Depart: 11/05/2026

One-way

Basic

From
$163
Seen: 6 hrs ago

Oklahoma City (OKC)to

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

One-way

Basic

From
$163
Seen: 2 hrs ago

Oklahoma City (OKC)to

Chicago-Midway (MDW)
Depart: 10/12/2026

One-way

Basic

From
$163
Seen: 9 hrs ago

Oklahoma City (OKC)to

Chicago-Midway (MDW)
Depart: 09/28/2026

One-way

Basic

From
$163
Seen: 5 hrs ago

Oklahoma City (OKC)to

Chicago-Midway (MDW)
Depart: 09/29/2026

One-way

Basic

From
$163
Seen: 6 hrs ago

Oklahoma City (OKC)to

Chicago-Midway (MDW)
Depart: 09/30/2026

One-way

Basic

From
$163
Seen: 6 hrs ago

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Explore flights from Oklahoma City to Chicago-Midway

Sep 2026
From$163*
Seen: 5 hrs ago
One Way/Basic
Oct 2026
From$163*
Seen: 9 hrs ago
One Way/Basic
Nov 2026
From$163*
Seen: 6 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $163
cmp-daily-histogram-bars-legend-max-price-aria-label $281
Displaying fares for September-2026
  • OKC–MDW, 09/08/2026: From $243
    08

    Tue

    SEP

  • OKC–MDW, 09/09/2026: From $243
    09

    Wed

  • OKC–MDW, 09/10/2026: From $271
    10

    Thu

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

    Fri

  • OKC–MDW, 09/12/2026: From $243
    12

    Sat

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

    Sun

  • OKC–MDW, 09/14/2026: From $271
    14

    Mon

  • OKC–MDW, 09/15/2026: From $243
    15

    Tue

  • OKC–MDW, 09/16/2026: From $243
    16

    Wed

  • OKC–MDW, 09/17/2026: From $271
    17

    Thu

  • OKC–MDW, 09/18/2026: From $281
    18

    Fri

  • OKC–MDW, 09/19/2026: From $243
    19

    Sat

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

    Sun

  • OKC–MDW, 09/21/2026: From $244
    21

    Mon

  • OKC–MDW, 09/22/2026: From $243
    22

    Tue

  • OKC–MDW, 09/23/2026: From $243
    23

    Wed

  • OKC–MDW, 09/24/2026: From $244
    24

    Thu

  • OKC–MDW, 09/25/2026: From $254
    25

    Fri

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

    Sat

  • OKC–MDW, 09/27/2026: From $244
    27

    Sun

  • OKC–MDW, 09/28/2026: From $163
    28

    Mon

  • OKC–MDW, 09/29/2026: From $163
    29

    Tue

  • OKC–MDW, 09/30/2026: From $163
    30

    Wed

  • OKC–MDW, 10/01/2026: From $173
    01

    Thu

    OCT

  • OKC–MDW, 10/02/2026: From $184
    02

    Fri

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

    Sat

  • OKC–MDW, 10/04/2026: From $223
    04

    Sun

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

    Mon

  • OKC–MDW: cmp-view-offers-disclaimer. Find Offers
    06

    Tue

  • OKC–MDW, 10/07/2026: From $173
    07

    Wed

    • Range$163-$281

    *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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