Southwest® flights from Long Island/Islip MacArthur to Chicago (O'Hare)

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Low fares from Long Island/Islip MacArthur to Chicago (O'Hare)

$

Long Island/Islip MacArthur (ISP)to

Chicago (Midway) (MDW)
Depart: 09/05/2026

One-way

Basic

From
$156
Seen: 20 hrs ago

Long Island/Islip MacArthur (ISP)to

Chicago (Midway) (MDW)
Depart: 09/11/2026

One-way

Basic

From
$156
Seen: 9 hrs ago

Long Island/Islip MacArthur (ISP)to

Chicago (Midway) (MDW)
Depart: 10/31/2026

One-way

Basic

From
$168
Seen: 16 hrs ago

Long Island/Islip MacArthur (ISP)to

Chicago (Midway) (MDW)
Depart: 10/07/2026

One-way

Basic

From
$168
Seen: 12 hrs ago

Long Island/Islip MacArthur (ISP)to

Chicago (Midway) (MDW)
Depart: 08/25/2026

One-way

Basic

From
$168
Seen: 13 hrs ago

Long Island/Islip MacArthur (ISP)to

Chicago (Midway) (MDW)
Depart: 09/19/2026

One-way

Basic

From
$168
Seen: 10 hrs ago

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Explore flights from Long Island/Islip MacArthur to Chicago (O'Hare)

Aug 2026
From$168*
Seen: 13 hrs ago
One Way/Basic
Sep 2026
From$156*
Seen: 20 hrs ago
One Way/Basic
Oct 2026
From$168*
Seen: 19 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $168
cmp-daily-histogram-bars-legend-max-price-aria-label $519
Displaying fares for August-2026
  • ISP–MDW: cmp-view-offers-disclaimer. Find Offers
    04

    Tue

    AUG

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

    Wed

  • ISP–MDW, 08/06/2026: From $519
    06

    Thu

  • ISP–MDW, 08/07/2026: From $519
    07

    Fri

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    08

    Sat

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

    Sun

  • ISP–MDW, 08/10/2026: From $394
    10

    Mon

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

    Tue

  • ISP–MDW, 08/12/2026: From $394
    12

    Wed

  • ISP–MDW: cmp-view-offers-disclaimer. Find Offers
    13

    Thu

  • ISP–MDW, 08/14/2026: From $394
    14

    Fri

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

    Sat

  • ISP–MDW, 08/16/2026: From $389
    16

    Sun

  • ISP–MDW, 08/17/2026: From $249
    17

    Mon

  • ISP–MDW, 08/18/2026: From $249
    18

    Tue

  • ISP–MDW, 08/19/2026: From $249
    19

    Wed

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

    Thu

  • ISP–MDW, 08/21/2026: From $249
    21

    Fri

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

    Sat

  • ISP–MDW, 08/23/2026: From $249
    23

    Sun

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

    Mon

  • ISP–MDW, 08/25/2026: From $168
    25

    Tue

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

    Wed

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

    Thu

  • ISP–MDW, 08/28/2026: From $189
    28

    Fri

  • ISP–MDW, 08/29/2026: From $168
    29

    Sat

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    30

    Sun

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

    Mon

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

    Tue

    SEP

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    02

    Wed

  • ISP–MDW, 09/03/2026: From $173
    03

    Thu

    • Range$168-$519

    *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:
    O'Hare International Airport
    Distance:
    773 miles

    Route Information

    42† 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 42 weekly flights from Long Island/Islip MacArthur to Chicago (O'Hare) on Southwest Airlines.
    To find the lowest fares by day and time to fly Long Island/Islip MacArthur to Chicago (O'Hare) with Southwest, check out our Low Fare Calendar.
    You can rent a car at O'Hare International Airport book yours with your flight.
    Yes! Flights from Long Island/Islip MacArthur to Chicago (O'Hare)—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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