Southwest® flights from Long Island/Islip MacArthur to Chicago-Midway from $170

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

$

Long Island/Islip MacArthur (ISP)to

Chicago-Midway (MDW)
Depart: 10/28/2026

One-way

Basic

From
$170
Seen: 19 hrs ago

Long Island/Islip MacArthur (ISP)to

Chicago-Midway (MDW)
Depart: 10/20/2026

One-way

Basic

From
$170
Seen: 21 hrs ago

Long Island/Islip MacArthur (ISP)to

Chicago-Midway (MDW)
Depart: 11/23/2026

One-way

Basic

From
$170
Seen: 6 hrs ago

Long Island/Islip MacArthur (ISP)to

Chicago-Midway (MDW)
Depart: 11/10/2026

One-way

Basic

From
$170
Seen: 1 hour ago

Long Island/Islip MacArthur (ISP)to

Chicago-Midway (MDW)
Depart: 11/11/2026

One-way

Basic

From
$170
Seen: 16 hrs ago

Long Island/Islip MacArthur (ISP)to

Chicago-Midway (MDW)
Depart: 11/21/2026

One-way

Basic

From
$170
Seen: 12 hrs ago

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

Sep 2026
From$529*
Seen: 9 hrs ago
One Way/Basic
Oct 2026
From$170*
Seen: 5 hrs ago
One Way/Basic
Nov 2026
From$170*
Seen: 6 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $170
cmp-daily-histogram-bars-legend-max-price-aria-label $529
Displaying fares for September-2026
  • ISP–MDW, 09/30/2026: From $529
    30

    Wed

    SEP

  • ISP–MDW, 10/01/2026: From $529
    01

    Thu

  • ISP–MDW, 10/02/2026: From $529
    02

    Fri

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    03

    Sat

  • ISP–MDW, 10/04/2026: From $529
    04

    Sun

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

    Mon

  • ISP–MDW, 10/06/2026: From $404
    06

    Tue

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    07

    Wed

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    08

    Thu

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    09

    Fri

  • ISP–MDW, 10/10/2026: From $404
    10

    Sat

  • ISP–MDW, 10/11/2026: From $404
    11

    Sun

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    12

    Mon

  • ISP–MDW, 10/13/2026: From $259
    13

    Tue

  • ISP–MDW, 10/14/2026: From $259
    14

    Wed

  • ISP–MDW, 10/15/2026: From $259
    15

    Thu

  • ISP–MDW, 10/16/2026: From $259
    16

    Fri

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    17

    Sat

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    18

    Sun

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    19

    Mon

  • ISP–MDW, 10/20/2026: From $170
    20

    Tue

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

    Wed

  • ISP–MDW, 10/22/2026: From $170
    22

    Thu

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    23

    Fri

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    24

    Sat

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    25

    Sun

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    26

    Mon

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

    Tue

  • ISP–MDW, 10/28/2026: From $170
    28

    Wed

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

    Thu

    • Range$170-$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:
    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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