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

Promo Code

Low fares from Oklahoma City to Chicago (Midway)

$

Oklahoma City (OKC)to

Chicago (Midway) (MDW)
Depart: 09/02/2026

One-way

Basic

From
$119
Seen: 16 hrs ago

Oklahoma City (OKC)to

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

One-way

Basic

From
$119
Seen: 13 hrs ago

Oklahoma City (OKC)to

Chicago (Midway) (MDW)
Depart: 08/19/2026

One-way

Basic

From
$119
Seen: 12 hrs ago

Oklahoma City (OKC)to

Chicago (Midway) (MDW)
Depart: 10/01/2026

One-way

Basic

From
$119
Seen: 7 hrs ago

Oklahoma City (OKC)to

Chicago (Midway) (MDW)
Depart: 08/26/2026

One-way

Basic

From
$119
Seen: 4 hrs ago

Oklahoma City (OKC)to

Chicago (Midway) (MDW)
Depart: 08/20/2026

One-way

Basic

From
$119
Seen: 23 hrs ago

Looking for more low-fare flights?

Check out the Low Fare Calendar to find a fare that works for you. Just choose the month you want to depart and return, and we’ll show you the best fares available.

Find low fares

Explore flights from Oklahoma City to Chicago (Midway)

Jul 2026
From$261*
Seen: 4 hrs ago
One Way/Basic
Aug 2026
From$119*
Seen: 23 hrs ago
One Way/Basic
Sep 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 $280
Displaying fares for July-2026
  • OKC–MDW, 07/30/2026: From $261
    30

    Thu

    JUL

  • OKC–MDW, 07/31/2026: From $261
    31

    Fri

  • OKC–MDW, 08/01/2026: From $233
    01

    Sat

    AUG

  • OKC–MDW, 08/02/2026: From $261
    02

    Sun

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

    Mon

  • OKC–MDW: cmp-view-offers-disclaimer. Find Offers
    04

    Tue

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

    Wed

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

    Thu

  • OKC–MDW, 08/07/2026: From $280
    07

    Fri

  • OKC–MDW, 08/08/2026: From $243
    08

    Sat

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

    Sun

  • OKC–MDW, 08/10/2026: From $280
    10

    Mon

  • OKC–MDW, 08/11/2026: From $270
    11

    Tue

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

    Wed

  • OKC–MDW, 08/13/2026: From $234
    13

    Thu

  • OKC–MDW, 08/14/2026: From $234
    14

    Fri

  • OKC–MDW, 08/15/2026: From $234
    15

    Sat

  • OKC–MDW, 08/16/2026: From $234
    16

    Sun

  • OKC–MDW, 08/17/2026: From $234
    17

    Mon

  • OKC–MDW, 08/18/2026: From $234
    18

    Tue

  • OKC–MDW, 08/19/2026: From $119
    19

    Wed

  • OKC–MDW, 08/20/2026: From $119
    20

    Thu

  • OKC–MDW: cmp-view-offers-disclaimer. Find Offers
    21

    Fri

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

    Sat

  • OKC–MDW, 08/23/2026: From $213
    23

    Sun

  • OKC–MDW, 08/24/2026: From $119
    24

    Mon

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

    Tue

  • OKC–MDW, 08/26/2026: From $119
    26

    Wed

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

    Thu

  • OKC–MDW, 08/28/2026: From $167
    28

    Fri

  • OKC–MDW: cmp-view-offers-disclaimer. Find Offers
    29

    Sat

    • Range$119-$280

    *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.

    Explore Flights from Other Popular Origins

    Popular Flights from Oklahoma City