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: 10/30/2026

One-way

Basic

From
$109
Seen: 1 hour ago

Omaha (OMA)to

Chicago (Midway) (MDW)
Depart: 09/06/2026

One-way

Basic

From
$109
Seen: 1 minute ago

Omaha (OMA)to

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

One-way

Basic

From
$109
Seen: 46 minutes ago

Omaha (OMA)to

Chicago (Midway) (MDW)
Depart: 09/23/2026

One-way

Basic

From
$128
Seen: 18 hrs ago

Omaha (OMA)to

Chicago (Midway) (MDW)
Depart: 09/16/2026

One-way

Basic

From
$128
Seen: 8 hrs ago

Omaha (OMA)to

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

One-way

Basic

From
$128
Seen: 14 hrs ago

Looking for more low-fare flights?

Check out the Low Fare Calendar to find a fare that works for you. Just choose the month you want to depart and return, and we’ll show you the best fares available.

Find low fares

Explore flights from Omaha to Chicago (Midway)

Aug 2026
From$128*
Seen: 5 hrs ago
One Way/Basic
Sep 2026
From$109*
Seen: 46 minutes ago
One Way/Basic
Oct 2026
From$109*
Seen: 1 hour ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $128
cmp-daily-histogram-bars-legend-max-price-aria-label $271
Displaying fares for August-2026
  • OMA–MDW, 08/01/2026: From $241
    01

    Sat

    AUG

  • OMA–MDW, 08/02/2026: From $266
    02

    Sun

  • OMA–MDW, 08/03/2026: From $266
    03

    Mon

  • OMA–MDW, 08/04/2026: From $241
    04

    Tue

  • OMA–MDW, 08/05/2026: From $241
    05

    Wed

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

    Thu

  • OMA–MDW, 08/07/2026: From $271
    07

    Fri

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

    Sat

  • OMA–MDW: cmp-view-offers-disclaimer. Find Offers
    09

    Sun

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

    Mon

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

    Tue

  • OMA–MDW, 08/12/2026: From $241
    12

    Wed

  • OMA–MDW, 08/13/2026: From $271
    13

    Thu

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

    Fri

  • OMA–MDW, 08/15/2026: From $225
    15

    Sat

  • OMA–MDW, 08/16/2026: From $225
    16

    Sun

  • OMA–MDW, 08/17/2026: From $225
    17

    Mon

  • OMA–MDW, 08/18/2026: From $225
    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 $151
    21

    Fri

  • OMA–MDW: cmp-view-offers-disclaimer. Find Offers
    22

    Sat

  • OMA–MDW, 08/23/2026: From $185
    23

    Sun

  • OMA–MDW, 08/24/2026: From $128
    24

    Mon

  • OMA–MDW: cmp-view-offers-disclaimer. Find Offers
    25

    Tue

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

    Wed

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

    Thu

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

    Fri

  • OMA–MDW: cmp-view-offers-disclaimer. Find Offers
    29

    Sat

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

    Sun

  • OMA–MDW, 08/31/2026: From $128
    31

    Mon

    • Range$128-$271

    *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.

    Explore Flights from Other Popular Origins

    Popular Flights from Omaha