Southwest® flights from Oklahoma City to Chicago-Midway from $160

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Low fares from Oklahoma City to Chicago-Midway

$

Oklahoma City (OKC)to

Chicago-Midway (MDW)
Depart: 12/22/2026

One-way

Basic

From
$160
Seen: 18 hrs ago

Oklahoma City (OKC)to

Chicago-Midway (MDW)
Depart: 12/02/2026

One-way

Basic

From
$160
Seen: 14 hrs ago

Oklahoma City (OKC)to

Chicago-Midway (MDW)
Depart: 12/01/2026

One-way

Basic

From
$160
Seen: 4 hrs ago

Oklahoma City (OKC)to

Chicago-Midway (MDW)
Depart: 01/23/2027

One-way

Basic

From
$160
Seen: 18 hrs ago

Oklahoma City (OKC)to

Chicago-Midway (MDW)
Depart: 02/13/2027

One-way

Basic

From
$160
Seen: 22 hrs ago

Oklahoma City (OKC)to

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

One-way

Basic

From
$160
Seen: 2 hrs ago

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Explore flights from Oklahoma City to Chicago-Midway

Nov 2026
From$268*
Seen: 23 hrs ago
One Way/Basic
Dec 2026
From$160*
Seen: 2 hrs ago
One Way/Basic
Jan 2027
From$160*
Seen: 18 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $160
cmp-daily-histogram-bars-legend-max-price-aria-label $296
Displaying fares for November-2026
  • OKC–MDW, 11/09/2026: From $296
    09

    Mon

    NOV

  • OKC–MDW, 11/10/2026: From $268
    10

    Tue

  • OKC–MDW, 11/11/2026: From $268
    11

    Wed

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

    Thu

  • OKC–MDW, 11/13/2026: From $296
    13

    Fri

  • OKC–MDW, 11/14/2026: From $268
    14

    Sat

  • OKC–MDW, 11/15/2026: From $296
    15

    Sun

  • OKC–MDW, 11/16/2026: From $296
    16

    Mon

  • OKC–MDW, 11/17/2026: From $268
    17

    Tue

  • OKC–MDW, 11/18/2026: From $268
    18

    Wed

  • OKC–MDW, 11/19/2026: From $296
    19

    Thu

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

    Fri

  • OKC–MDW, 11/21/2026: From $268
    21

    Sat

  • OKC–MDW, 11/22/2026: From $269
    22

    Sun

  • OKC–MDW, 11/23/2026: From $269
    23

    Mon

  • OKC–MDW, 11/24/2026: From $268
    24

    Tue

  • OKC–MDW, 11/25/2026: From $268
    25

    Wed

  • OKC–MDW, 11/26/2026: From $269
    26

    Thu

  • OKC–MDW: cmp-view-offers-disclaimer. Find Offers
    27

    Fri

  • OKC–MDW, 11/28/2026: From $268
    28

    Sat

  • OKC–MDW, 11/29/2026: From $269
    29

    Sun

  • OKC–MDW, 11/30/2026: From $269
    30

    Mon

  • OKC–MDW, 12/01/2026: From $160
    01

    Tue

    DEC

  • OKC–MDW, 12/02/2026: From $160
    02

    Wed

  • OKC–MDW, 12/03/2026: From $175
    03

    Thu

  • OKC–MDW, 12/04/2026: From $185
    04

    Fri

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

    Sat

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

    Sun

  • OKC–MDW, 12/07/2026: From $175
    07

    Mon

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

    Tue

    • Range$160-$296

    *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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