Southwest® flights from Chicago-Midway to Long Island/Islip MacArthur from $187

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

$

Chicago-Midway (MDW)to

Long Island/Islip MacArthur (ISP)
Depart: 01/06/2027

One-way

Basic

From
$187
Seen: 2 hrs ago

Chicago-Midway (MDW)to

Long Island/Islip MacArthur (ISP)
Depart: 12/16/2026

One-way

Basic

From
$187
Seen: 17 hrs ago

Chicago-Midway (MDW)to

Long Island/Islip MacArthur (ISP)
Depart: 12/08/2026

One-way

Basic

From
$187
Seen: 19 hrs ago

Chicago-Midway (MDW)to

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

One-way

Basic

From
$187
Seen: 22 hrs ago

Chicago-Midway (MDW)to

Long Island/Islip MacArthur (ISP)
Depart: 12/03/2026

One-way

Basic

From
$207
Seen: 18 hrs ago

Chicago-Midway (MDW)to

Long Island/Islip MacArthur (ISP)
Depart: 12/07/2026

One-way

Basic

From
$207
Seen: 20 hrs ago

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

Nov 2026
From$274*
Seen: 16 hrs ago
One Way/Basic
Dec 2026
From$187*
Seen: 22 hrs ago
One Way/Basic
Jan 2027
From$187*
Seen: 2 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $187
cmp-daily-histogram-bars-legend-max-price-aria-label $544
Displaying fares for November-2026
  • MDW–ISP, 11/12/2026: From $544
    12

    Thu

    NOV

  • MDW–ISP, 11/13/2026: From $544
    13

    Fri

  • MDW–ISP: cmp-view-offers-disclaimer. Find Offers
    14

    Sat

  • MDW–ISP, 11/15/2026: From $544
    15

    Sun

  • MDW–ISP, 11/16/2026: From $544
    16

    Mon

  • MDW–ISP, 11/17/2026: From $544
    17

    Tue

  • MDW–ISP: cmp-view-offers-disclaimer. Find Offers
    18

    Wed

  • MDW–ISP, 11/19/2026: From $419
    19

    Thu

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

    Fri

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

    Sat

  • MDW–ISP: cmp-view-offers-disclaimer. Find Offers
    22

    Sun

  • MDW–ISP: cmp-view-offers-disclaimer. Find Offers
    23

    Mon

  • MDW–ISP, 11/24/2026: From $419
    24

    Tue

  • MDW–ISP, 11/25/2026: From $274
    25

    Wed

  • MDW–ISP, 11/26/2026: From $274
    26

    Thu

  • MDW–ISP: cmp-view-offers-disclaimer. Find Offers
    27

    Fri

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

    Sat

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

    Sun

  • MDW–ISP, 11/30/2026: From $304
    30

    Mon

  • MDW–ISP, 12/01/2026: From $274
    01

    Tue

    DEC

  • MDW–ISP: cmp-view-offers-disclaimer. Find Offers
    02

    Wed

  • MDW–ISP, 12/03/2026: From $207
    03

    Thu

  • MDW–ISP: cmp-view-offers-disclaimer. Find Offers
    04

    Fri

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

    Sat

  • MDW–ISP, 12/06/2026: From $249
    06

    Sun

  • MDW–ISP, 12/07/2026: From $207
    07

    Mon

  • MDW–ISP, 12/08/2026: From $187
    08

    Tue

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

    Wed

  • MDW–ISP, 12/10/2026: From $207
    10

    Thu

  • MDW–ISP, 12/11/2026: From $234
    11

    Fri

    • Range$187-$544

    *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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