Southwest® flights from Omaha to Chicago (O'Hare)

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Low fares from Omaha to Chicago (O'Hare)

$

Omaha (OMA)to

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

One-way

Basic

From
$129
Seen: 23 hrs ago

Omaha (OMA)to

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

One-way

Basic

From
$129
Seen: 10 hrs ago

Omaha (OMA)to

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

One-way

Basic

From
$129
Seen: 10 hrs ago

Omaha (OMA)to

Chicago (Midway) (MDW)
Depart: 09/21/2026

One-way

Basic

From
$129
Seen: 12 hrs ago

Omaha (OMA)to

Chicago (Midway) (MDW)
Depart: 09/29/2026

One-way

Basic

From
$129
Seen: 2 hrs ago

Omaha (OMA)to

Chicago (Midway) (MDW)
Depart: 10/28/2026

One-way

Basic

From
$129
Seen: 2 hrs ago

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Explore flights from Omaha to Chicago (O'Hare)

Aug 2026
From$241*
Seen: 14 hrs ago
One Way/Basic
Sep 2026
From$129*
Seen: 19 hrs ago
One Way/Basic
Oct 2026
From$129*
Seen: 21 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $129
cmp-daily-histogram-bars-legend-max-price-aria-label $266
Displaying fares for August-2026
  • OMA–MDW, 08/25/2026: From $241
    25

    Tue

    AUG

  • OMA–MDW, 08/26/2026: From $241
    26

    Wed

  • OMA–MDW, 08/27/2026: From $266
    27

    Thu

  • OMA–MDW, 08/28/2026: From $266
    28

    Fri

  • OMA–MDW, 08/29/2026: From $241
    29

    Sat

  • OMA–MDW, 08/30/2026: From $266
    30

    Sun

  • OMA–MDW, 08/31/2026: From $266
    31

    Mon

  • OMA–MDW, 09/01/2026: From $241
    01

    Tue

    SEP

  • OMA–MDW, 09/02/2026: From $241
    02

    Wed

  • OMA–MDW, 09/03/2026: From $266
    03

    Thu

  • OMA–MDW, 09/04/2026: From $266
    04

    Fri

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

    Sat

  • OMA–MDW, 09/06/2026: From $193
    06

    Sun

  • OMA–MDW, 09/07/2026: From $225
    07

    Mon

  • OMA–MDW, 09/08/2026: From $225
    08

    Tue

  • OMA–MDW, 09/09/2026: From $193
    09

    Wed

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

    Thu

  • OMA–MDW, 09/11/2026: From $193
    11

    Fri

  • OMA–MDW, 09/12/2026: From $193
    12

    Sat

  • OMA–MDW, 09/13/2026: From $225
    13

    Sun

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

    Mon

  • OMA–MDW, 09/15/2026: From $129
    15

    Tue

  • OMA–MDW: cmp-view-offers-disclaimer. Find Offers
    16

    Wed

  • OMA–MDW, 09/17/2026: From $140
    17

    Thu

  • OMA–MDW, 09/18/2026: From $140
    18

    Fri

  • OMA–MDW, 09/19/2026: From $129
    19

    Sat

  • OMA–MDW, 09/20/2026: From $185
    20

    Sun

  • OMA–MDW, 09/21/2026: From $129
    21

    Mon

  • OMA–MDW, 09/22/2026: From $129
    22

    Tue

  • OMA–MDW: cmp-view-offers-disclaimer. Find Offers
    23

    Wed

  • OMA–MDW, 09/24/2026: From $155
    24

    Thu

    • Range$129-$266

    *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:
    O'Hare International Airport
    Distance:
    416 miles

    Route Information

    41† Weekly flights

    † 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

    There are 41 weekly flights from Omaha to Chicago (O'Hare) on Southwest Airlines.
    To find the lowest fares by day and time to fly Omaha to Chicago (O'Hare) with Southwest, check out our Low Fare Calendar.
    You can rent a car at O'Hare International Airport book yours with your flight.
    Yes! Flights from Omaha to Chicago (O'Hare)—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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