Southwest® flights from Long Island/Islip MacArthur to Chicago-Midway from $182

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

$

Long Island/Islip MacArthur (ISP)to

Chicago-Midway (MDW)
Depart: 02/06/2027

One-way

Basic

From
$182
Seen: 19 hrs ago

Long Island/Islip MacArthur (ISP)to

Chicago-Midway (MDW)
Depart: 12/19/2026

One-way

Basic

From
$182
Seen: 3 hrs ago

Long Island/Islip MacArthur (ISP)to

Chicago-Midway (MDW)
Depart: 01/12/2027

One-way

Basic

From
$182
Seen: 24 minutes ago

Long Island/Islip MacArthur (ISP)to

Chicago-Midway (MDW)
Depart: 12/09/2026

One-way

Basic

From
$187
Seen: 13 hrs ago

Long Island/Islip MacArthur (ISP)to

Chicago-Midway (MDW)
Depart: 12/10/2026

One-way

Basic

From
$197
Seen: 1 hour ago

Long Island/Islip MacArthur (ISP)to

Chicago-Midway (MDW)
Depart: 01/11/2027

One-way

Basic

From
$197
Seen: 9 hrs ago

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

Nov 2026
From$274*
Seen: 1 hour ago
One Way/Basic
Dec 2026
From$182*
Seen: 3 hrs ago
One Way/Basic
Jan 2027
From$182*
Seen: 24 minutes ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $207
Displaying fares for November-2026
  • ISP–MDW: cmp-view-offers-disclaimer. Find Offers
    09

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    NOV

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    10

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

    Wed

  • ISP–MDW, 11/12/2026: From $544
    12

    Thu

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

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    14

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    15

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    16

    Mon

  • ISP–MDW, 11/17/2026: From $419
    17

    Tue

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    18

    Wed

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    19

    Thu

  • ISP–MDW, 11/20/2026: From $419
    20

    Fri

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

    Sat

  • ISP–MDW, 11/22/2026: From $274
    22

    Sun

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    23

    Mon

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    24

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    25

    Wed

  • ISP–MDW, 11/26/2026: From $279
    26

    Thu

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

    Fri

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

    Sat

  • ISP–MDW, 11/29/2026: From $351
    29

    Sun

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    30

    Mon

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

    Tue

    DEC

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    02

    Wed

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

    Thu

  • ISP–MDW, 12/04/2026: From $207
    04

    Fri

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    05

    Sat

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    06

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    07

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    08

    Tue

    • Range$207-$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:
    Long Island MacArthur Airport
    Arriving at:
    Chicago Midway International Airport
    Distance:
    765 miles

    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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