Southwest® flights from Omaha to Chicago-Midway from $109

Promo Code

Low fares from Omaha to Chicago-Midway

$

Omaha (OMA)to

Chicago-Midway (MDW)
Depart: 10/03/2026

One-way

Basic

From
$109
Seen: 20 hrs ago

Omaha (OMA)to

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

One-way

Basic

From
$109
Seen: 23 hrs ago

Omaha (OMA)to

Chicago-Midway (MDW)
Depart: 10/17/2026

One-way

Basic

From
$109
Seen: 13 hrs ago

Omaha (OMA)to

Chicago-Midway (MDW)
Depart: 12/10/2026

One-way

Basic

From
$109
Seen: 10 hrs ago

Omaha (OMA)to

Chicago-Midway (MDW)
Depart: 10/13/2026

One-way

Basic

From
$109
Seen: 9 hrs ago

Omaha (OMA)to

Chicago-Midway (MDW)
Depart: 11/14/2026

One-way

Basic

From
$109
Seen: 6 hrs ago

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Explore flights from Omaha to Chicago-Midway

Sep 2026
From$109*
Seen: 14 hrs ago
One Way/Basic
Oct 2026
From$109*
Seen: 18 hrs ago
One Way/Basic
Nov 2026
From$109*
Seen: 20 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $109
cmp-daily-histogram-bars-legend-max-price-aria-label $276
Displaying fares for September-2026
  • OMA–MDW, 09/11/2026: From $276
    11

    Fri

    SEP

  • OMA–MDW, 09/12/2026: From $251
    12

    Sat

  • OMA–MDW, 09/13/2026: From $276
    13

    Sun

  • OMA–MDW, 09/14/2026: From $276
    14

    Mon

  • OMA–MDW, 09/15/2026: From $251
    15

    Tue

  • OMA–MDW, 09/16/2026: From $251
    16

    Wed

  • OMA–MDW, 09/17/2026: From $276
    17

    Thu

  • OMA–MDW, 09/18/2026: From $276
    18

    Fri

  • OMA–MDW, 09/19/2026: From $251
    19

    Sat

  • OMA–MDW, 09/20/2026: From $276
    20

    Sun

  • OMA–MDW, 09/21/2026: From $276
    21

    Mon

  • OMA–MDW, 09/22/2026: From $251
    22

    Tue

  • OMA–MDW, 09/23/2026: From $245
    23

    Wed

  • OMA–MDW, 09/24/2026: From $235
    24

    Thu

  • OMA–MDW, 09/25/2026: From $235
    25

    Fri

  • OMA–MDW, 09/26/2026: From $245
    26

    Sat

  • OMA–MDW, 09/27/2026: From $235
    27

    Sun

  • OMA–MDW, 09/28/2026: From $235
    28

    Mon

  • OMA–MDW, 09/29/2026: From $235
    29

    Tue

  • OMA–MDW, 09/30/2026: From $109
    30

    Wed

  • OMA–MDW, 10/01/2026: From $109
    01

    Thu

    OCT

  • OMA–MDW, 10/02/2026: From $138
    02

    Fri

  • OMA–MDW, 10/03/2026: From $109
    03

    Sat

  • OMA–MDW, 10/04/2026: From $195
    04

    Sun

  • OMA–MDW, 10/05/2026: From $109
    05

    Mon

  • OMA–MDW, 10/06/2026: From $109
    06

    Tue

  • OMA–MDW, 10/07/2026: From $109
    07

    Wed

  • OMA–MDW, 10/08/2026: From $195
    08

    Thu

  • OMA–MDW, 10/09/2026: From $205
    09

    Fri

  • OMA–MDW, 10/10/2026: From $109
    10

    Sat

    • Range$109-$276

    *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

    Route Information

    150† Weekly flights
    • 4‡ Nonstop flights per day Monday through Friday
    • 3‡ Nonstop flights on Saturday
    • 5‡ 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 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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