Southwest® flights from Chicago-Midway to Long Island/Islip MacArthur from $163

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

$

Chicago-Midway (MDW)to

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

One-way

Basic

From
$163
Seen: 18 hrs ago

Chicago-Midway (MDW)to

Long Island/Islip MacArthur (ISP)
Depart: 11/04/2026

One-way

Basic

From
$163
Seen: 11 hrs ago

Chicago-Midway (MDW)to

Long Island/Islip MacArthur (ISP)
Depart: 11/17/2026

One-way

Basic

From
$163
Seen: 12 hrs ago

Chicago-Midway (MDW)to

Long Island/Islip MacArthur (ISP)
Depart: 10/21/2026

One-way

Basic

From
$163
Seen: 11 hrs ago

Chicago-Midway (MDW)to

Long Island/Islip MacArthur (ISP)
Depart: 10/03/2026

One-way

Basic

From
$163
Seen: 13 hrs ago

Chicago-Midway (MDW)to

Long Island/Islip MacArthur (ISP)
Depart: 12/05/2026

One-way

Basic

From
$168
Seen: 16 hrs ago

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

Sep 2026
From$249*
Seen: 19 hrs ago
One Way/Basic
Oct 2026
From$163*
Seen: 13 hrs ago
One Way/Basic
Nov 2026
From$163*
Seen: 11 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $163
cmp-daily-histogram-bars-legend-max-price-aria-label $529
Displaying fares for September-2026
  • MDW–ISP, 09/12/2026: From $529
    12

    Sat

    SEP

  • MDW–ISP, 09/13/2026: From $529
    13

    Sun

  • MDW–ISP, 09/14/2026: From $529
    14

    Mon

  • MDW–ISP, 09/15/2026: From $529
    15

    Tue

  • MDW–ISP, 09/16/2026: From $529
    16

    Wed

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

    Thu

  • MDW–ISP, 09/18/2026: From $404
    18

    Fri

  • MDW–ISP, 09/19/2026: From $394
    19

    Sat

  • MDW–ISP, 09/20/2026: From $404
    20

    Sun

  • MDW–ISP, 09/21/2026: From $404
    21

    Mon

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

    Tue

  • MDW–ISP, 09/23/2026: From $404
    23

    Wed

  • MDW–ISP, 09/24/2026: From $249
    24

    Thu

  • MDW–ISP, 09/25/2026: From $259
    25

    Fri

  • MDW–ISP: cmp-view-offers-disclaimer. Find Offers
    26

    Sat

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

    Sun

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

    Mon

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

    Tue

  • MDW–ISP, 09/30/2026: From $259
    30

    Wed

  • MDW–ISP, 10/01/2026: From $168
    01

    Thu

    OCT

  • MDW–ISP, 10/02/2026: From $194
    02

    Fri

  • MDW–ISP, 10/03/2026: From $163
    03

    Sat

  • MDW–ISP, 10/04/2026: From $229
    04

    Sun

  • MDW–ISP, 10/05/2026: From $194
    05

    Mon

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

    Tue

  • MDW–ISP, 10/07/2026: From $194
    07

    Wed

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

    Thu

  • MDW–ISP, 10/09/2026: From $252
    09

    Fri

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

    Sat

  • MDW–ISP: cmp-view-offers-disclaimer. Find Offers
    11

    Sun

    • Range$163-$529

    *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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