Southwest® flights from New Orleans to Chicago (Midway) from $104

Promo Code

Low fares from New Orleans to Chicago (Midway)

$

New Orleans (MSY)to

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

One-way

Basic

From
$104
Seen: 16 hrs ago

New Orleans (MSY)to

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

One-way

Basic

From
$104
Seen: 17 hrs ago

New Orleans (MSY)to

Chicago (Midway) (MDW)
Depart: 09/05/2026

One-way

Basic

From
$104
Seen: 25 minutes ago

New Orleans (MSY)to

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

One-way

Basic

From
$114
Seen: 6 hrs ago

New Orleans (MSY)to

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

One-way

Basic

From
$118
Seen: 13 hrs ago

New Orleans (MSY)to

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

One-way

Basic

From
$118
Seen: 20 hrs ago

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Explore flights from New Orleans to Chicago (Midway)

Aug 2026
From$118*
Seen: 4 hrs ago
One Way/Basic
Sep 2026
From$104*
Seen: 17 hrs ago
One Way/Basic
Oct 2026
From$104*
Seen: 16 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $118
cmp-daily-histogram-bars-legend-max-price-aria-label $221
Displaying fares for August-2026
  • MSY–MDW, 08/02/2026: From $221
    02

    Sun

    AUG

  • MSY–MDW, 08/03/2026: From $221
    03

    Mon

  • MSY–MDW, 08/04/2026: From $182
    04

    Tue

  • MSY–MDW, 08/05/2026: From $182
    05

    Wed

  • MSY–MDW, 08/06/2026: From $221
    06

    Thu

  • MSY–MDW, 08/07/2026: From $221
    07

    Fri

  • MSY–MDW, 08/08/2026: From $182
    08

    Sat

  • MSY–MDW, 08/09/2026: From $221
    09

    Sun

  • MSY–MDW, 08/10/2026: From $221
    10

    Mon

  • MSY–MDW, 08/11/2026: From $182
    11

    Tue

  • MSY–MDW, 08/12/2026: From $182
    12

    Wed

  • MSY–MDW, 08/13/2026: From $221
    13

    Thu

  • MSY–MDW, 08/14/2026: From $221
    14

    Fri

  • MSY–MDW, 08/15/2026: From $182
    15

    Sat

  • MSY–MDW, 08/16/2026: From $221
    16

    Sun

  • MSY–MDW, 08/17/2026: From $221
    17

    Mon

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

    Tue

  • MSY–MDW, 08/19/2026: From $182
    19

    Wed

  • MSY–MDW, 08/20/2026: From $221
    20

    Thu

  • MSY–MDW, 08/21/2026: From $221
    21

    Fri

  • MSY–MDW, 08/22/2026: From $182
    22

    Sat

  • MSY–MDW, 08/23/2026: From $221
    23

    Sun

  • MSY–MDW, 08/24/2026: From $118
    24

    Mon

  • MSY–MDW, 08/25/2026: From $118
    25

    Tue

  • MSY–MDW, 08/26/2026: From $118
    26

    Wed

  • MSY–MDW, 08/27/2026: From $118
    27

    Thu

  • MSY–MDW, 08/28/2026: From $171
    28

    Fri

  • MSY–MDW, 08/29/2026: From $118
    29

    Sat

  • MSY–MDW, 08/30/2026: From $221
    30

    Sun

  • MSY–MDW, 08/31/2026: From $118
    31

    Mon

  • MSY–MDW, 09/01/2026: From $118
    01

    Tue

    SEP

    • Range$118-$221

    *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:
    Louis Armstrong International Airport
    Arriving at:
    Chicago Midway International Airport
    Average flight time:
    2 hours 19 minutes
    Distance:
    825 miles

    Route Information

    156† Weekly flights
    • 3‡ Nonstop flights per day Monday through Friday
    • 3‡ Nonstop flights on Saturday
    • 4‡ 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 New Orleans to Chicago (Midway) is 2 hours 19 minutes.
    There are 156 weekly flights from New Orleans to Chicago (Midway) on Southwest Airlines.
    Yes, Southwest flies nonstop from New Orleans to Chicago (Midway) 3 times per day from Monday through Friday.
    Yes, Southwest flies nonstop from New Orleans to Chicago (Midway) 3 times per day on Saturdays and 4 times per day on Sundays.
    To find the lowest fares by day and time to fly New Orleans 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 New Orleans 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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