Southwest® flights from New Orleans to Chicago (Midway) from $126

Promo Code

Low fares from New Orleans to Chicago (Midway)

$

New Orleans (MSY)to

Chicago (Midway) (MDW)
Depart: 11/04/2026

One-way

Basic

From
$126
Seen: 23 hrs ago

New Orleans (MSY)to

Chicago (Midway) (MDW)
Depart: 09/10/2026

One-way

Basic

From
$126
Seen: 22 hrs ago

New Orleans (MSY)to

Chicago (Midway) (MDW)
Depart: 09/12/2026

One-way

Basic

From
$126
Seen: 14 hrs ago

New Orleans (MSY)to

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

One-way

Basic

From
$126
Seen: 15 hrs ago

New Orleans (MSY)to

Chicago (Midway) (MDW)
Depart: 09/26/2026

One-way

Basic

From
$126
Seen: 5 hrs ago

New Orleans (MSY)to

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

One-way

Basic

From
$126
Seen: 3 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 New Orleans to Chicago (Midway)

Aug 2026
From$180*
Seen: 1 hour ago
One Way/Basic
Sep 2026
From$126*
Seen: 8 hrs ago
One Way/Basic
Oct 2026
From$126*
Seen: 11 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $126
cmp-daily-histogram-bars-legend-max-price-aria-label $296
Displaying fares for August-2026
  • MSY–MDW, 08/22/2026: From $229
    22

    Sat

    AUG

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

    Sun

  • MSY–MDW, 08/24/2026: From $180
    24

    Mon

  • MSY–MDW, 08/25/2026: From $182
    25

    Tue

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

    Wed

  • MSY–MDW, 08/27/2026: From $221
    27

    Thu

  • MSY–MDW, 08/28/2026: From $221
    28

    Fri

  • MSY–MDW, 08/29/2026: From $182
    29

    Sat

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

    Sun

  • MSY–MDW, 08/31/2026: From $221
    31

    Mon

  • MSY–MDW, 09/01/2026: From $182
    01

    Tue

    SEP

  • MSY–MDW, 09/02/2026: From $182
    02

    Wed

  • MSY–MDW, 09/03/2026: From $221
    03

    Thu

  • MSY–MDW, 09/04/2026: From $221
    04

    Fri

  • MSY–MDW, 09/05/2026: From $136
    05

    Sat

  • MSY–MDW, 09/06/2026: From $126
    06

    Sun

  • MSY–MDW, 09/07/2026: From $296
    07

    Mon

  • MSY–MDW, 09/08/2026: From $182
    08

    Tue

  • MSY–MDW, 09/09/2026: From $126
    09

    Wed

  • MSY–MDW, 09/10/2026: From $126
    10

    Thu

  • MSY–MDW, 09/11/2026: From $126
    11

    Fri

  • MSY–MDW, 09/12/2026: From $126
    12

    Sat

  • MSY–MDW, 09/13/2026: From $221
    13

    Sun

  • MSY–MDW, 09/14/2026: From $159
    14

    Mon

  • MSY–MDW, 09/15/2026: From $149
    15

    Tue

  • MSY–MDW, 09/16/2026: From $149
    16

    Wed

  • MSY–MDW, 09/17/2026: From $149
    17

    Thu

  • MSY–MDW, 09/18/2026: From $162
    18

    Fri

  • MSY–MDW, 09/19/2026: From $149
    19

    Sat

  • MSY–MDW, 09/20/2026: From $221
    20

    Sun

  • MSY–MDW, 09/21/2026: From $151
    21

    Mon

    • Range$126-$296

    *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.

    Explore Flights from Other Popular Origins

    Popular Flights from New Orleans