Southwest® flights from New Orleans to Chicago-Midway from $161

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Low fares from New Orleans to Chicago-Midway

$

New Orleans (MSY)to

Chicago-Midway (MDW)
Depart: 01/16/2027

One-way

Basic

From
$161
Seen: 20 hrs ago

New Orleans (MSY)to

Chicago-Midway (MDW)
Depart: 01/30/2027

One-way

Basic

From
$161
Seen: 22 hrs ago

New Orleans (MSY)to

Chicago-Midway (MDW)
Depart: 01/06/2027

One-way

Basic

From
$161
Seen: 11 hrs ago

New Orleans (MSY)to

Chicago-Midway (MDW)
Depart: 01/19/2027

One-way

Basic

From
$161
Seen: 22 hrs ago

New Orleans (MSY)to

Chicago-Midway (MDW)
Depart: 01/20/2027

One-way

Basic

From
$161
Seen: 16 hrs ago

New Orleans (MSY)to

Chicago-Midway (MDW)
Depart: 02/17/2027

One-way

Basic

From
$161
Seen: 4 hrs ago

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Explore flights from New Orleans to Chicago-Midway

Nov 2026
From$222*
Seen: 13 hrs ago
One Way/Basic
Dec 2026
From$166*
Seen: 3 hrs ago
One Way/Basic
Jan 2027
From$161*
Seen: 11 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $177
cmp-daily-histogram-bars-legend-max-price-aria-label $376
Displaying fares for November-2026
  • MSY–MDW, 11/13/2026: From $261
    13

    Fri

    NOV

  • MSY–MDW, 11/14/2026: From $222
    14

    Sat

  • MSY–MDW: cmp-view-offers-disclaimer. Find Offers
    15

    Sun

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

    Mon

  • MSY–MDW, 11/17/2026: From $222
    17

    Tue

  • MSY–MDW, 11/18/2026: From $222
    18

    Wed

  • MSY–MDW, 11/19/2026: From $261
    19

    Thu

  • MSY–MDW: cmp-view-offers-disclaimer. Find Offers
    20

    Fri

  • MSY–MDW, 11/21/2026: From $251
    21

    Sat

  • MSY–MDW, 11/22/2026: From $271
    22

    Sun

  • MSY–MDW, 11/23/2026: From $261
    23

    Mon

  • MSY–MDW, 11/24/2026: From $232
    24

    Tue

  • MSY–MDW, 11/25/2026: From $222
    25

    Wed

  • MSY–MDW, 11/26/2026: From $261
    26

    Thu

  • MSY–MDW, 11/27/2026: From $271
    27

    Fri

  • MSY–MDW, 11/28/2026: From $310
    28

    Sat

  • MSY–MDW, 11/29/2026: From $376
    29

    Sun

  • MSY–MDW, 11/30/2026: From $261
    30

    Mon

  • MSY–MDW, 12/01/2026: From $222
    01

    Tue

    DEC

  • MSY–MDW, 12/02/2026: From $222
    02

    Wed

  • MSY–MDW, 12/03/2026: From $261
    03

    Thu

  • MSY–MDW, 12/04/2026: From $217
    04

    Fri

  • MSY–MDW, 12/05/2026: From $177
    05

    Sat

  • MSY–MDW, 12/06/2026: From $266
    06

    Sun

  • MSY–MDW: cmp-view-offers-disclaimer. Find Offers
    07

    Mon

  • MSY–MDW: cmp-view-offers-disclaimer. Find Offers
    08

    Tue

  • MSY–MDW, 12/09/2026: From $177
    09

    Wed

  • MSY–MDW, 12/10/2026: From $197
    10

    Thu

  • MSY–MDW, 12/11/2026: From $217
    11

    Fri

  • MSY–MDW, 12/12/2026: From $197
    12

    Sat

    • Range$177-$376

    *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

    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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