Southwest® flights from Chicago (Midway) to Long Island/Islip MacArthur from $149

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

$

Chicago (Midway) (MDW)to

Long Island/Islip MacArthur (ISP)
Depart: 09/26/2026

One-way

Basic

From
$149
Seen: 6 hrs ago

Chicago (Midway) (MDW)to

Long Island/Islip MacArthur (ISP)
Depart: 09/30/2026

One-way

Basic

From
$149
Seen: 8 hrs ago

Chicago (Midway) (MDW)to

Long Island/Islip MacArthur (ISP)
Depart: 10/29/2026

One-way

Basic

From
$149
Seen: 4 hrs ago

Chicago (Midway) (MDW)to

Long Island/Islip MacArthur (ISP)
Depart: 11/12/2026

One-way

Basic

From
$149
Seen: 4 hrs ago

Chicago (Midway) (MDW)to

Long Island/Islip MacArthur (ISP)
Depart: 10/07/2026

One-way

Basic

From
$149
Seen: 9 hrs ago

Chicago (Midway) (MDW)to

Long Island/Islip MacArthur (ISP)
Depart: 09/12/2026

One-way

Basic

From
$149
Seen: 8 hrs ago

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

Aug 2026
From$394*
Seen: 23 hrs ago
One Way/Basic
Sep 2026
From$149*
Seen: 8 hrs ago
One Way/Basic
Oct 2026
From$149*
Seen: 9 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $149
cmp-daily-histogram-bars-legend-max-price-aria-label $519
Displaying fares for August-2026
  • MDW–ISP, 08/22/2026: From $519
    22

    Sat

    AUG

  • MDW–ISP, 08/23/2026: From $519
    23

    Sun

  • MDW–ISP, 08/24/2026: From $519
    24

    Mon

  • MDW–ISP, 08/25/2026: From $519
    25

    Tue

  • MDW–ISP, 08/26/2026: From $519
    26

    Wed

  • MDW–ISP, 08/27/2026: From $519
    27

    Thu

  • MDW–ISP, 08/28/2026: From $394
    28

    Fri

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

    Sat

  • MDW–ISP, 08/30/2026: From $394
    30

    Sun

  • MDW–ISP: cmp-view-offers-disclaimer. Find Offers
    31

    Mon

  • MDW–ISP: cmp-view-offers-disclaimer. Find Offers
    01

    Tue

    SEP

  • MDW–ISP, 09/02/2026: From $394
    02

    Wed

  • MDW–ISP: cmp-view-offers-disclaimer. Find Offers
    03

    Thu

  • MDW–ISP, 09/04/2026: From $249
    04

    Fri

  • MDW–ISP: cmp-view-offers-disclaimer. Find Offers
    05

    Sat

  • MDW–ISP: cmp-view-offers-disclaimer. Find Offers
    06

    Sun

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

    Mon

  • MDW–ISP, 09/08/2026: From $249
    08

    Tue

  • MDW–ISP, 09/09/2026: From $249
    09

    Wed

  • MDW–ISP, 09/10/2026: From $249
    10

    Thu

  • MDW–ISP, 09/11/2026: From $173
    11

    Fri

  • MDW–ISP, 09/12/2026: From $149
    12

    Sat

  • MDW–ISP, 09/13/2026: From $229
    13

    Sun

  • MDW–ISP, 09/14/2026: From $163
    14

    Mon

  • MDW–ISP, 09/15/2026: From $163
    15

    Tue

  • MDW–ISP, 09/16/2026: From $163
    16

    Wed

  • MDW–ISP, 09/17/2026: From $237
    17

    Thu

  • MDW–ISP, 09/18/2026: From $224
    18

    Fri

  • MDW–ISP: cmp-view-offers-disclaimer. Find Offers
    19

    Sat

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

    Sun

  • MDW–ISP: cmp-view-offers-disclaimer. Find Offers
    21

    Mon

    • Range$149-$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:
    Chicago Midway International Airport
    Arriving at:
    Long Island MacArthur Airport
    Distance:
    765 miles

    Route Information

    80† 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 80 weekly flights from Chicago (Midway) to Long Island/Islip MacArthur on Southwest Airlines.
    To find the lowest fares by day and time to fly Chicago (Midway) to Long Island/Islip MacArthur with Southwest, check out our Low Fare Calendar.
    You can rent a car at Long Island MacArthur Airport book yours with your flight.
    Yes! Flights from Chicago (Midway) to Long Island/Islip MacArthur—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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