Southwest® flights from Chicago-Midway to Long Island/Islip MacArthur from $147

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Low fares from Chicago-Midway to Long Island/Islip MacArthur

$

Chicago-Midway (MDW)to

Long Island/Islip MacArthur (ISP)
Depart: 12/19/2026

One-way

Basic

From
$147
Seen: 12 hrs ago

Chicago-Midway (MDW)to

Long Island/Islip MacArthur (ISP)
Depart: 01/25/2027

One-way

Basic

From
$147
Seen: 3 hrs ago

Chicago-Midway (MDW)to

Long Island/Islip MacArthur (ISP)
Depart: 12/31/2026

One-way

Basic

From
$153
Seen: 8 minutes ago

Chicago-Midway (MDW)to

Long Island/Islip MacArthur (ISP)
Depart: 11/16/2026

One-way

Basic

From
$153
Seen: 19 hrs ago

Chicago-Midway (MDW)to

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

One-way

Basic

From
$153
Seen: 4 hrs ago

Chicago-Midway (MDW)to

Long Island/Islip MacArthur (ISP)
Depart: 11/18/2026

One-way

Basic

From
$153
Seen: 13 hrs ago

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Explore flights from Chicago-Midway to Long Island/Islip MacArthur

Oct 2026
From$414*
Seen: 23 hrs ago
One Way/Basic
Nov 2026
From$153*
Seen: 19 hrs ago
One Way/Basic
Dec 2026
From$147*
Seen: 12 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $153
cmp-daily-histogram-bars-legend-max-price-aria-label $539
Displaying fares for October-2026
  • MDW–ISP: cmp-view-offers-disclaimer. Find Offers
    22

    Thu

    OCT

  • MDW–ISP, 10/23/2026: From $539
    23

    Fri

  • MDW–ISP: cmp-view-offers-disclaimer. Find Offers
    24

    Sat

  • MDW–ISP: cmp-view-offers-disclaimer. Find Offers
    25

    Sun

  • MDW–ISP, 10/26/2026: From $539
    26

    Mon

  • MDW–ISP, 10/27/2026: From $539
    27

    Tue

  • MDW–ISP: cmp-view-offers-disclaimer. Find Offers
    28

    Wed

  • MDW–ISP, 10/29/2026: From $414
    29

    Thu

  • MDW–ISP, 10/30/2026: From $414
    30

    Fri

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

    Sat

  • MDW–ISP, 11/01/2026: From $414
    01

    Sun

    NOV

  • MDW–ISP, 11/02/2026: From $414
    02

    Mon

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

    Tue

  • MDW–ISP, 11/04/2026: From $269
    04

    Wed

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

    Thu

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

    Fri

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

    Sat

  • MDW–ISP, 11/08/2026: From $295
    08

    Sun

  • MDW–ISP: cmp-view-offers-disclaimer. Find Offers
    09

    Mon

  • MDW–ISP: cmp-view-offers-disclaimer. Find Offers
    10

    Tue

  • MDW–ISP, 11/11/2026: From $153
    11

    Wed

  • MDW–ISP, 11/12/2026: From $239
    12

    Thu

  • MDW–ISP, 11/13/2026: From $156
    13

    Fri

  • MDW–ISP, 11/14/2026: From $159
    14

    Sat

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

    Sun

  • MDW–ISP, 11/16/2026: From $153
    16

    Mon

  • MDW–ISP: cmp-view-offers-disclaimer. Find Offers
    17

    Tue

  • MDW–ISP, 11/18/2026: From $153
    18

    Wed

  • MDW–ISP, 11/19/2026: From $239
    19

    Thu

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

    Fri

  • MDW–ISP, 11/21/2026: From $419
    21

    Sat

    • Range$153-$539

    *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

    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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