Southwest® flights from Long Island/Islip MacArthur to Chicago (Midway) from $156

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Low fares from Long Island/Islip MacArthur to Chicago (Midway)

$

Long Island/Islip MacArthur (ISP)to

Chicago (Midway) (MDW)
Depart: 10/31/2026

One-way

Basic

From
$156
Seen: 21 hrs ago

Long Island/Islip MacArthur (ISP)to

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

One-way

Basic

From
$156
Seen: 22 hrs ago

Long Island/Islip MacArthur (ISP)to

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

One-way

Basic

From
$156
Seen: 21 hrs ago

Long Island/Islip MacArthur (ISP)to

Chicago (Midway) (MDW)
Depart: 09/19/2026

One-way

Basic

From
$168
Seen: 14 hrs ago

Long Island/Islip MacArthur (ISP)to

Chicago (Midway) (MDW)
Depart: 10/05/2026

One-way

Basic

From
$168
Seen: 2 hrs ago

Long Island/Islip MacArthur (ISP)to

Chicago (Midway) (MDW)
Depart: 10/21/2026

One-way

Basic

From
$168
Seen: 15 hrs ago

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Explore flights from Long Island/Islip MacArthur to Chicago (Midway)

Aug 2026
From$168*
Seen: 16 hrs ago
One Way/Basic
Sep 2026
From$156*
Seen: 22 hrs ago
One Way/Basic
Oct 2026
From$156*
Seen: 21 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $168
Displaying fares for August-2026
  • ISP–MDW, 08/01/2026: From $519
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  • ISP–MDW, 08/02/2026: From $519
    02

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  • ISP–MDW, 08/04/2026: From $519
    04

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  • ISP–MDW, 08/06/2026: From $519
    06

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  • ISP–MDW, 08/10/2026: From $394
    10

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    11

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    12

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  • ISP–MDW, 08/13/2026: From $394
    13

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    14

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    18

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    19

    Wed

  • ISP–MDW, 08/20/2026: From $249
    20

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    21

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    22

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    23

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  • ISP–MDW, 08/24/2026: From $168
    24

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    25

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    26

    Wed

  • ISP–MDW, 08/27/2026: From $168
    27

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    28

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    31

    Mon

    • Range$168-$519

    *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:
    Long Island MacArthur Airport
    Arriving at:
    Chicago Midway International Airport
    Distance:
    765 miles

    Route Information

    88† 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 88 weekly flights from Long Island/Islip MacArthur to Chicago (Midway) on Southwest Airlines.
    To find the lowest fares by day and time to fly Long Island/Islip MacArthur 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 Long Island/Islip MacArthur 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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