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: 09/08/2026

One-way

Basic

From
$119
Seen: 57 minutes ago

New York (LaGuardia) (LGA)to

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

One-way

Basic

From
$124
Seen: 22 hrs ago

New York (LaGuardia) (LGA)to

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

One-way

Basic

From
$124
Seen: 22 hrs ago

New York (LaGuardia) (LGA)to

Chicago (Midway) (MDW)
Depart: 11/14/2026

One-way

Basic

From
$124
Seen: 22 hrs ago

New York (LaGuardia) (LGA)to

Chicago (Midway) (MDW)
Depart: 09/15/2026

One-way

Basic

From
$124
Seen: 22 hrs ago

New York (LaGuardia) (LGA)to

Chicago (Midway) (MDW)
Depart: 12/02/2026

One-way

Basic

From
$124
Seen: 19 hrs ago

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

Aug 2026
From$143*
Seen: 21 hrs ago
One Way/Basic
Sep 2026
From$119*
Seen: 57 minutes ago
One Way/Basic
Oct 2026
From$124*
Seen: 22 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $119
cmp-daily-histogram-bars-legend-max-price-aria-label $204
Displaying fares for August-2026
  • LGA–MDW, 08/26/2026: From $143
    26

    Wed

    AUG

  • LGA–MDW, 08/27/2026: From $168
    27

    Thu

  • LGA–MDW, 08/28/2026: From $168
    28

    Fri

  • LGA–MDW, 08/29/2026: From $143
    29

    Sat

  • LGA–MDW, 08/30/2026: From $168
    30

    Sun

  • LGA–MDW, 08/31/2026: From $168
    31

    Mon

  • LGA–MDW, 09/01/2026: From $143
    01

    Tue

    SEP

  • LGA–MDW, 09/02/2026: From $143
    02

    Wed

  • LGA–MDW, 09/03/2026: From $204
    03

    Thu

  • LGA–MDW, 09/04/2026: From $178
    04

    Fri

  • LGA–MDW, 09/05/2026: From $143
    05

    Sat

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

    Sun

  • LGA–MDW, 09/07/2026: From $159
    07

    Mon

  • LGA–MDW, 09/08/2026: From $119
    08

    Tue

  • LGA–MDW, 09/09/2026: From $143
    09

    Wed

  • LGA–MDW, 09/10/2026: From $148
    10

    Thu

  • LGA–MDW, 09/11/2026: From $148
    11

    Fri

  • LGA–MDW, 09/12/2026: From $153
    12

    Sat

  • LGA–MDW, 09/13/2026: From $168
    13

    Sun

  • LGA–MDW: cmp-view-offers-disclaimer. Find Offers
    14

    Mon

  • LGA–MDW, 09/15/2026: From $124
    15

    Tue

  • LGA–MDW, 09/16/2026: From $124
    16

    Wed

  • LGA–MDW, 09/17/2026: From $124
    17

    Thu

  • LGA–MDW, 09/18/2026: From $134
    18

    Fri

  • LGA–MDW, 09/19/2026: From $124
    19

    Sat

  • LGA–MDW, 09/20/2026: From $124
    20

    Sun

  • LGA–MDW, 09/21/2026: From $124
    21

    Mon

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

    Tue

  • LGA–MDW: cmp-view-offers-disclaimer. Find Offers
    23

    Wed

  • LGA–MDW, 09/24/2026: From $124
    24

    Thu

  • LGA–MDW, 09/25/2026: From $124
    25

    Fri

    • Range$119-$204

    *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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