Southwest® flights from Chicago-Midway to Midland/Odessa from $197

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Low fares from Chicago-Midway to Midland/Odessa

$

Chicago-Midway (MDW)to

Midland/Odessa (MAF)
Depart: 01/06/2027

One-way

Basic

From
$197
Seen: 5 hrs ago

Chicago-Midway (MDW)to

Midland/Odessa (MAF)
Depart: 01/05/2027

One-way

Basic

From
$197
Seen: 4 hrs ago

Chicago-Midway (MDW)to

Midland/Odessa (MAF)
Depart: 12/18/2026

One-way

Basic

From
$222
Seen: 14 minutes ago

Chicago-Midway (MDW)to

Midland/Odessa (MAF)
Depart: 12/14/2026

One-way

Basic

From
$234
Seen: 7 hrs ago

Chicago-Midway (MDW)to

Midland/Odessa (MAF)
Depart: 01/05/2027

One-way

Choice

From
$242
Seen: 4 hrs ago

Chicago-Midway (MDW)to

Midland/Odessa (MAF)
Depart: 01/06/2027

One-way

Choice

From
$242
Seen: 5 hrs ago

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Explore flights from Chicago-Midway to Midland/Odessa

Nov 2026
From$309*
Seen: 7 hrs ago
One Way/Basic
Dec 2026
From$222*
Seen: 14 minutes ago
One Way/Basic
Jan 2027
From$197*
Seen: 5 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $309
Displaying fares for November-2026
  • MDW–MAF: cmp-view-offers-disclaimer. Find Offers
    10

    Tue

    NOV

  • MDW–MAF, 11/11/2026: From $309
    11

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  • MDW–MAF, 11/12/2026: From $358
    12

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  • MDW–MAF, 11/13/2026: From $358
    13

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    18

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  • MDW–MAF, 11/19/2026: From $358
    19

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    20

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    21

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    22

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    23

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    24

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    25

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    26

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    27

    Fri

  • MDW–MAF, 11/28/2026: From $358
    28

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    29

    Sun

  • MDW–MAF, 11/30/2026: From $314
    30

    Mon

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    01

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    DEC

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    09

    Wed

    • Range$309-$358

    *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:
    Chicago Midway International Airport
    Arriving at:
    Midland International Airport
    Distance:
    1047 miles

    Questions we hear the most

    There are 120 weekly flights from Chicago (Midway) to Midland/Odessa on Southwest Airlines.
    To find the lowest fares by day and time to fly Chicago (Midway) to Midland/Odessa with Southwest, check out our Low Fare Calendar.
    You can rent a car at Midland International Airport book yours with your flight.
    Yes! Flights from Chicago (Midway) to Midland/Odessa—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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