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

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Low fares from Omaha to Chicago-Midway

$

Omaha (OMA)to

Chicago-Midway (MDW)
Depart: 11/03/2026

One-way

Basic

From
$109
Seen: 7 hrs ago

Omaha (OMA)to

Chicago-Midway (MDW)
Depart: 01/06/2027

One-way

Basic

From
$109
Seen: 8 hrs ago

Omaha (OMA)to

Chicago-Midway (MDW)
Depart: 11/19/2026

One-way

Basic

From
$109
Seen: 7 hrs ago

Omaha (OMA)to

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

One-way

Basic

From
$109
Seen: 13 hrs ago

Omaha (OMA)to

Chicago-Midway (MDW)
Depart: 12/07/2026

One-way

Basic

From
$109
Seen: 18 hrs ago

Omaha (OMA)to

Chicago-Midway (MDW)
Depart: 10/22/2026

One-way

Basic

From
$109
Seen: 15 hrs ago

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Explore flights from Omaha to Chicago-Midway

Oct 2026
From$109*
Seen: 15 hrs ago
One Way/Basic
Nov 2026
From$109*
Seen: 23 hrs ago
One Way/Basic
Dec 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 $291
Displaying fares for October-2026
  • OMA–MDW, 10/02/2026: From $286
    02

    Fri

    OCT

  • OMA–MDW, 10/03/2026: From $261
    03

    Sat

  • OMA–MDW, 10/04/2026: From $286
    04

    Sun

  • OMA–MDW, 10/05/2026: From $286
    05

    Mon

  • OMA–MDW, 10/06/2026: From $261
    06

    Tue

  • OMA–MDW, 10/07/2026: From $261
    07

    Wed

  • OMA–MDW, 10/08/2026: From $291
    08

    Thu

  • OMA–MDW, 10/09/2026: From $286
    09

    Fri

  • OMA–MDW: cmp-view-offers-disclaimer. Find Offers
    10

    Sat

  • OMA–MDW, 10/11/2026: From $286
    11

    Sun

  • OMA–MDW, 10/12/2026: From $286
    12

    Mon

  • OMA–MDW, 10/13/2026: From $261
    13

    Tue

  • OMA–MDW, 10/14/2026: From $261
    14

    Wed

  • OMA–MDW, 10/15/2026: From $245
    15

    Thu

  • OMA–MDW, 10/16/2026: From $245
    16

    Fri

  • OMA–MDW, 10/17/2026: From $245
    17

    Sat

  • OMA–MDW, 10/18/2026: From $245
    18

    Sun

  • OMA–MDW: cmp-view-offers-disclaimer. Find Offers
    19

    Mon

  • OMA–MDW, 10/20/2026: From $245
    20

    Tue

  • OMA–MDW, 10/21/2026: From $245
    21

    Wed

  • OMA–MDW, 10/22/2026: From $109
    22

    Thu

  • OMA–MDW, 10/23/2026: From $171
    23

    Fri

  • OMA–MDW, 10/24/2026: From $109
    24

    Sat

  • OMA–MDW, 10/25/2026: From $205
    25

    Sun

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

    Mon

  • OMA–MDW: cmp-view-offers-disclaimer. Find Offers
    27

    Tue

  • OMA–MDW, 10/28/2026: From $109
    28

    Wed

  • OMA–MDW, 10/29/2026: From $109
    29

    Thu

  • OMA–MDW, 10/30/2026: From $148
    30

    Fri

  • OMA–MDW, 10/31/2026: From $109
    31

    Sat

  • OMA–MDW, 11/01/2026: From $194
    01

    Sun

    NOV

    • Range$109-$291

    *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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