Southwest® flights from Chicago-Midway to Midland/Odessa from $147

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Low fares from Chicago-Midway to Midland/Odessa

$

Chicago-Midway (MDW)to

Midland/Odessa (MAF)
Depart: 11/12/2026

One-way

Basic

From
$147
Seen: 50 minutes ago

Chicago-Midway (MDW)to

Midland/Odessa (MAF)
Depart: 12/25/2026

One-way

Basic

From
$161
Seen: 1 hour ago

Chicago-Midway (MDW)to

Midland/Odessa (MAF)
Depart: 11/13/2026

One-way

Basic

From
$161
Seen: 1 hour ago

Chicago-Midway (MDW)to

Midland/Odessa (MAF)
Depart: 11/12/2026

One-way

Choice

From
$196
Seen: 50 minutes ago

Chicago-Midway (MDW)to

Midland/Odessa (MAF)
Depart: 12/20/2026

One-way

Basic

From
$208
Seen: 11 hrs ago

Chicago-Midway (MDW)to

Midland/Odessa (MAF)
Depart: 11/13/2026

One-way

Choice

From
$233
Seen: 1 hour ago

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Explore flights from Chicago-Midway to Midland/Odessa

Oct 2026
From$304*
Seen: 7 hrs ago
One Way/Basic
Nov 2026
From$147*
Seen: 50 minutes ago
One Way/Basic
Dec 2026
From$161*
Seen: 1 hour ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $147
Displaying fares for October-2026
  • MDW–MAF, 10/20/2026: From $304
    20

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    OCT

  • MDW–MAF, 10/21/2026: From $304
    21

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  • MDW–MAF, 10/28/2026: From $304
    28

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    NOV

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  • MDW–MAF, 11/06/2026: From $279
    06

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  • MDW–MAF, 11/08/2026: From $279
    08

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    11

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  • MDW–MAF, 11/12/2026: From $147
    12

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  • MDW–MAF, 11/13/2026: From $161
    13

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    14

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    16

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    • Range$147-$304

    *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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