Southwest® flights from New York (LaGuardia) to Chicago (O'Hare)

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Low fares from New York (LaGuardia) to Chicago (O'Hare)

$

New York (LaGuardia) (LGA)to

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

One-way

Basic

From
$114
Seen: 5 hrs ago

New York (LaGuardia) (LGA)to

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

One-way

Basic

From
$114
Seen: 3 hrs ago

New York (LaGuardia) (LGA)to

Chicago (Midway) (MDW)
Depart: 09/08/2026

One-way

Basic

From
$114
Seen: 8 hrs ago

New York (LaGuardia) (LGA)to

Chicago (Midway) (MDW)
Depart: 09/02/2026

One-way

Basic

From
$114
Seen: 8 hrs ago

New York (LaGuardia) (LGA)to

Chicago (Midway) (MDW)
Depart: 08/26/2026

One-way

Basic

From
$114
Seen: 5 hrs ago

New York (LaGuardia) (LGA)to

Chicago (Midway) (MDW)
Depart: 08/29/2026

One-way

Basic

From
$114
Seen: 2 hrs ago

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Explore flights from New York (LaGuardia) to Chicago (O'Hare)

Aug 2026
From$114*
Seen: 3 hrs ago
One Way/Basic
Sep 2026
From$114*
Seen: 8 hrs ago
One Way/Basic
Oct 2026
From$119*
Seen: 19 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $114
cmp-daily-histogram-bars-legend-max-price-aria-label $233
Displaying fares for August-2026
  • LGA–MDW, 08/06/2026: From $229
    06

    Thu

    AUG

  • LGA–MDW, 08/07/2026: From $229
    07

    Fri

  • LGA–MDW, 08/08/2026: From $194
    08

    Sat

  • LGA–MDW, 08/09/2026: From $229
    09

    Sun

  • LGA–MDW, 08/10/2026: From $229
    10

    Mon

  • LGA–MDW, 08/11/2026: From $183
    11

    Tue

  • LGA–MDW, 08/12/2026: From $134
    12

    Wed

  • LGA–MDW, 08/13/2026: From $203
    13

    Thu

  • LGA–MDW, 08/14/2026: From $233
    14

    Fri

  • LGA–MDW, 08/15/2026: From $203
    15

    Sat

  • LGA–MDW, 08/16/2026: From $223
    16

    Sun

  • LGA–MDW, 08/17/2026: From $144
    17

    Mon

  • LGA–MDW, 08/18/2026: From $134
    18

    Tue

  • LGA–MDW, 08/19/2026: From $134
    19

    Wed

  • LGA–MDW, 08/20/2026: From $134
    20

    Thu

  • LGA–MDW, 08/21/2026: From $168
    21

    Fri

  • LGA–MDW, 08/22/2026: From $134
    22

    Sat

  • LGA–MDW, 08/23/2026: From $168
    23

    Sun

  • LGA–MDW, 08/24/2026: From $134
    24

    Mon

  • LGA–MDW, 08/25/2026: From $114
    25

    Tue

  • LGA–MDW, 08/26/2026: From $114
    26

    Wed

  • LGA–MDW, 08/27/2026: From $124
    27

    Thu

  • LGA–MDW, 08/28/2026: From $124
    28

    Fri

  • LGA–MDW, 08/29/2026: From $114
    29

    Sat

  • LGA–MDW, 08/30/2026: From $124
    30

    Sun

  • LGA–MDW, 08/31/2026: From $124
    31

    Mon

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

    Tue

    SEP

  • LGA–MDW, 09/02/2026: From $114
    02

    Wed

  • LGA–MDW, 09/03/2026: From $124
    03

    Thu

  • LGA–MDW, 09/04/2026: From $134
    04

    Fri

  • LGA–MDW, 09/05/2026: From $114
    05

    Sat

    • Range$114-$233

    *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:
    La Guardia Airport
    Arriving at:
    O'Hare International Airport
    Distance:
    733 miles

    Route Information

    67† 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 67 weekly flights from New York (LaGuardia) to Chicago (O'Hare) on Southwest Airlines.
    To find the lowest fares by day and time to fly New York (LaGuardia) 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 New York (LaGuardia) 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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