Southwest® flights from Omaha to Chicago-Midway from $119

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Low fares from Omaha to Chicago-Midway

$

Omaha (OMA)to

Chicago-Midway (MDW)
Depart: 12/09/2026

One-way

Basic

From
$119
Seen: 1 hour ago

Omaha (OMA)to

Chicago-Midway (MDW)
Depart: 01/08/2027

One-way

Basic

From
$119
Seen: 52 minutes ago

Omaha (OMA)to

Chicago-Midway (MDW)
Depart: 12/18/2026

One-way

Basic

From
$119
Seen: 4 minutes ago

Omaha (OMA)to

Chicago-Midway (MDW)
Depart: 11/09/2026

One-way

Basic

From
$121
Seen: 1 hour ago

Omaha (OMA)to

Chicago-Midway (MDW)
Depart: 12/11/2026

One-way

Basic

From
$122
Seen: 21 hrs ago

Omaha (OMA)to

Chicago-Midway (MDW)
Depart: 11/22/2026

One-way

Basic

From
$122
Seen: 23 hrs ago

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Explore flights from Omaha to Chicago-Midway

Oct 2026
From$255*
Seen: 1 hour ago
One Way/Basic
Nov 2026
From$121*
Seen: 1 hour ago
One Way/Basic
Dec 2026
From$119*
Seen: 4 minutes ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $121
cmp-daily-histogram-bars-legend-max-price-aria-label $296
Displaying fares for October-2026
  • OMA–MDW, 10/23/2026: From $296
    23

    Fri

    OCT

  • OMA–MDW, 10/24/2026: From $255
    24

    Sat

  • OMA–MDW, 10/25/2026: From $296
    25

    Sun

  • OMA–MDW, 10/26/2026: From $296
    26

    Mon

  • OMA–MDW, 10/27/2026: From $256
    27

    Tue

  • OMA–MDW, 10/28/2026: From $256
    28

    Wed

  • OMA–MDW, 10/29/2026: From $296
    29

    Thu

  • OMA–MDW, 10/30/2026: From $296
    30

    Fri

  • OMA–MDW, 10/31/2026: From $256
    31

    Sat

  • OMA–MDW, 11/01/2026: From $296
    01

    Sun

    NOV

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

    Mon

  • OMA–MDW, 11/03/2026: From $269
    03

    Tue

  • OMA–MDW, 11/04/2026: From $256
    04

    Wed

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

    Thu

  • OMA–MDW, 11/06/2026: From $265
    06

    Fri

  • OMA–MDW, 11/07/2026: From $255
    07

    Sat

  • OMA–MDW: cmp-view-offers-disclaimer. Find Offers
    08

    Sun

  • OMA–MDW, 11/09/2026: From $121
    09

    Mon

  • OMA–MDW, 11/10/2026: From $122
    10

    Tue

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

    Wed

  • OMA–MDW, 11/12/2026: From $132
    12

    Thu

  • OMA–MDW, 11/13/2026: From $129
    13

    Fri

  • OMA–MDW, 11/14/2026: From $122
    14

    Sat

  • OMA–MDW, 11/15/2026: From $122
    15

    Sun

  • OMA–MDW, 11/16/2026: From $122
    16

    Mon

  • OMA–MDW: cmp-view-offers-disclaimer. Find Offers
    17

    Tue

  • OMA–MDW, 11/18/2026: From $122
    18

    Wed

  • OMA–MDW, 11/19/2026: From $122
    19

    Thu

  • OMA–MDW, 11/20/2026: From $157
    20

    Fri

  • OMA–MDW, 11/21/2026: From $122
    21

    Sat

  • OMA–MDW, 11/22/2026: From $122
    22

    Sun

    • Range$121-$296

    *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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