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: 09/06/2026

One-way

Basic

From
$109
Seen: 11 hrs ago

Omaha (OMA)to

Chicago (Midway) (MDW)
Depart: 10/30/2026

One-way

Basic

From
$109
Seen: 4 hrs ago

Omaha (OMA)to

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

One-way

Basic

From
$109
Seen: 14 hrs ago

Omaha (OMA)to

Chicago (Midway) (MDW)
Depart: 09/02/2026

One-way

Basic

From
$128
Seen: 23 hrs ago

Omaha (OMA)to

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

One-way

Basic

From
$128
Seen: 21 hrs ago

Omaha (OMA)to

Chicago (Midway) (MDW)
Depart: 08/25/2026

One-way

Basic

From
$128
Seen: 20 hrs ago

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Explore flights from Omaha to Chicago (O'Hare)

Aug 2026
From$128*
Seen: 10 hrs ago
One Way/Basic
Sep 2026
From$109*
Seen: 14 hrs ago
One Way/Basic
Oct 2026
From$109*
Seen: 4 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $128
cmp-daily-histogram-bars-legend-max-price-aria-label $266
Displaying fares for August-2026
  • OMA–MDW, 08/05/2026: From $241
    05

    Wed

    AUG

  • OMA–MDW, 08/06/2026: From $266
    06

    Thu

  • OMA–MDW, 08/07/2026: From $266
    07

    Fri

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

    Sat

  • OMA–MDW, 08/09/2026: From $266
    09

    Sun

  • OMA–MDW, 08/10/2026: From $266
    10

    Mon

  • OMA–MDW, 08/11/2026: From $241
    11

    Tue

  • OMA–MDW: cmp-view-offers-disclaimer. Find Offers
    12

    Wed

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

    Thu

  • OMA–MDW, 08/14/2026: From $266
    14

    Fri

  • OMA–MDW, 08/15/2026: From $241
    15

    Sat

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

    Sun

  • OMA–MDW, 08/17/2026: From $266
    17

    Mon

  • OMA–MDW: cmp-view-offers-disclaimer. Find Offers
    18

    Tue

  • OMA–MDW, 08/19/2026: From $225
    19

    Wed

  • OMA–MDW, 08/20/2026: From $225
    20

    Thu

  • OMA–MDW, 08/21/2026: From $225
    21

    Fri

  • OMA–MDW, 08/22/2026: From $225
    22

    Sat

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

    Sun

  • OMA–MDW, 08/24/2026: From $225
    24

    Mon

  • OMA–MDW, 08/25/2026: From $128
    25

    Tue

  • OMA–MDW, 08/26/2026: From $128
    26

    Wed

  • OMA–MDW, 08/27/2026: From $128
    27

    Thu

  • OMA–MDW, 08/28/2026: From $151
    28

    Fri

  • OMA–MDW, 08/29/2026: From $128
    29

    Sat

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

    Sun

  • OMA–MDW: cmp-view-offers-disclaimer. Find Offers
    31

    Mon

  • OMA–MDW, 09/01/2026: From $128
    01

    Tue

    SEP

  • OMA–MDW, 09/02/2026: From $128
    02

    Wed

  • OMA–MDW, 09/03/2026: From $184
    03

    Thu

  • OMA–MDW, 09/04/2026: From $205
    04

    Fri

    • Range$128-$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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