Southwest® flights from Omaha to Chicago-Midway from $125

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Low fares from Omaha to Chicago-Midway

$

Omaha (OMA)to

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

One-way

Basic

From
$125
Seen: 15 hrs ago

Omaha (OMA)to

Chicago-Midway (MDW)
Depart: 12/19/2026

One-way

Basic

From
$125
Seen: 23 hrs ago

Omaha (OMA)to

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

One-way

Basic

From
$125
Seen: 7 hrs ago

Omaha (OMA)to

Chicago-Midway (MDW)
Depart: 01/20/2027

One-way

Basic

From
$125
Seen: 9 hrs ago

Omaha (OMA)to

Chicago-Midway (MDW)
Depart: 01/12/2027

One-way

Basic

From
$125
Seen: 23 hrs ago

Omaha (OMA)to

Chicago-Midway (MDW)
Depart: 12/15/2026

One-way

Basic

From
$125
Seen: 22 hrs ago

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Explore flights from Omaha to Chicago-Midway

Nov 2026
From$250*
Seen: 8 hrs ago
One Way/Basic
Dec 2026
From$125*
Seen: 22 hrs ago
One Way/Basic
Jan 2027
From$125*
Seen: 22 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $125
cmp-daily-histogram-bars-legend-max-price-aria-label $250
Displaying fares for November-2026
  • OMA–MDW, 11/12/2026: From $250
    12

    Thu

    NOV

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

    Fri

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

    Sat

  • OMA–MDW: cmp-view-offers-disclaimer. Find Offers
    15

    Sun

  • OMA–MDW, 11/16/2026: From $250
    16

    Mon

  • OMA–MDW, 11/17/2026: From $250
    17

    Tue

  • OMA–MDW, 11/18/2026: From $250
    18

    Wed

  • OMA–MDW, 11/19/2026: From $250
    19

    Thu

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

    Fri

  • OMA–MDW, 11/21/2026: From $250
    21

    Sat

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

    Sun

  • OMA–MDW, 11/23/2026: From $250
    23

    Mon

  • OMA–MDW, 11/24/2026: From $250
    24

    Tue

  • OMA–MDW, 11/25/2026: From $250
    25

    Wed

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

    Thu

  • OMA–MDW, 11/27/2026: From $250
    27

    Fri

  • OMA–MDW: cmp-view-offers-disclaimer. Find Offers
    28

    Sat

  • OMA–MDW, 11/29/2026: From $250
    29

    Sun

  • OMA–MDW: cmp-view-offers-disclaimer. Find Offers
    30

    Mon

  • OMA–MDW, 12/01/2026: From $250
    01

    Tue

    DEC

  • OMA–MDW, 12/02/2026: From $125
    02

    Wed

  • OMA–MDW, 12/03/2026: From $145
    03

    Thu

  • OMA–MDW, 12/04/2026: From $160
    04

    Fri

  • OMA–MDW, 12/05/2026: From $125
    05

    Sat

  • OMA–MDW, 12/06/2026: From $220
    06

    Sun

  • OMA–MDW, 12/07/2026: From $145
    07

    Mon

  • OMA–MDW, 12/08/2026: From $125
    08

    Tue

  • OMA–MDW, 12/09/2026: From $125
    09

    Wed

  • OMA–MDW, 12/10/2026: From $145
    10

    Thu

  • OMA–MDW, 12/11/2026: From $160
    11

    Fri

    • Range$125-$250

    *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:
    Eppley Airfield
    Arriving at:
    Chicago Midway International Airport
    Average flight time:
    1 hour 26 minutes
    Distance:
    423 miles

    Questions we hear the most

    The average flight time from Omaha to Chicago (Midway) is 1 hour 26 minutes.
    There are 150 weekly flights from Omaha to Chicago (Midway) on Southwest Airlines.
    Yes, Southwest flies nonstop from Omaha to Chicago (Midway) 4 times per day from Monday through Friday.
    Yes, Southwest flies nonstop from Omaha to Chicago (Midway) 3 times per day on Saturdays and 5 times per day on Sundays.
    To find the lowest fares by day and time to fly Omaha 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 Omaha 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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