Southwest® flights from Oklahoma City to Chicago-Midway from $165

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Low fares from Oklahoma City to Chicago-Midway

$

Oklahoma City (OKC)to

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

One-way

Basic

From
$165
Seen: 19 hrs ago

Oklahoma City (OKC)to

Chicago-Midway (MDW)
Depart: 01/19/2027

One-way

Basic

From
$165
Seen: 3 hrs ago

Oklahoma City (OKC)to

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

One-way

Basic

From
$165
Seen: 6 hrs ago

Oklahoma City (OKC)to

Chicago-Midway (MDW)
Depart: 12/08/2026

One-way

Basic

From
$165
Seen: 16 hrs ago

Oklahoma City (OKC)to

Chicago-Midway (MDW)
Depart: 12/29/2026

One-way

Basic

From
$165
Seen: 18 hrs ago

Oklahoma City (OKC)to

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

One-way

Basic

From
$165
Seen: 20 hrs ago

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Explore flights from Oklahoma City to Chicago-Midway

Nov 2026
From$273*
Seen: 13 hrs ago
One Way/Basic
Dec 2026
From$165*
Seen: 16 hrs ago
One Way/Basic
Jan 2027
From$165*
Seen: 4 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $165
cmp-daily-histogram-bars-legend-max-price-aria-label $301
Displaying fares for November-2026
  • OKC–MDW: cmp-view-offers-disclaimer. Find Offers
    15

    Sun

    NOV

  • OKC–MDW: cmp-view-offers-disclaimer. Find Offers
    16

    Mon

  • OKC–MDW, 11/17/2026: From $273
    17

    Tue

  • OKC–MDW, 11/18/2026: From $273
    18

    Wed

  • OKC–MDW, 11/19/2026: From $301
    19

    Thu

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

    Fri

  • OKC–MDW, 11/21/2026: From $273
    21

    Sat

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

    Sun

  • OKC–MDW, 11/23/2026: From $301
    23

    Mon

  • OKC–MDW, 11/24/2026: From $273
    24

    Tue

  • OKC–MDW, 11/25/2026: From $273
    25

    Wed

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

    Thu

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

    Fri

  • OKC–MDW, 11/28/2026: From $273
    28

    Sat

  • OKC–MDW, 11/29/2026: From $301
    29

    Sun

  • OKC–MDW, 11/30/2026: From $274
    30

    Mon

  • OKC–MDW, 12/01/2026: From $221
    01

    Tue

    DEC

  • OKC–MDW: cmp-view-offers-disclaimer. Find Offers
    02

    Wed

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

    Thu

  • OKC–MDW, 12/04/2026: From $274
    04

    Fri

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

    Sat

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

    Sun

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

    Mon

  • OKC–MDW, 12/08/2026: From $165
    08

    Tue

  • OKC–MDW, 12/09/2026: From $165
    09

    Wed

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

    Thu

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

    Fri

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

    Sat

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

    Sun

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

    Mon

    • Range$165-$301

    *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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