Southwest® flights from Chicago-Midway to New York LaGuardia from $165

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Low fares from Chicago-Midway to New York LaGuardia

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Chicago-Midway (MDW)to

New York LaGuardia (LGA)
Depart: 01/19/2027

One-way

Basic

From
$165
Seen: 21 hrs ago

Chicago-Midway (MDW)to

New York LaGuardia (LGA)
Depart: 02/10/2027

One-way

Basic

From
$165
Seen: 14 hrs ago

Chicago-Midway (MDW)to

New York LaGuardia (LGA)
Depart: 01/13/2027

One-way

Basic

From
$165
Seen: 14 hrs ago

Chicago-Midway (MDW)to

New York LaGuardia (LGA)
Depart: 12/16/2026

One-way

Basic

From
$165
Seen: 16 hrs ago

Chicago-Midway (MDW)to

New York LaGuardia (LGA)
Depart: 02/03/2027

One-way

Basic

From
$165
Seen: 6 hrs ago

Chicago-Midway (MDW)to

New York LaGuardia (LGA)
Depart: 01/27/2027

One-way

Basic

From
$165
Seen: 33 minutes ago
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Explore flights from Chicago-Midway to New York LaGuardia

cmp-daily-histogram-bars-legend-min-price-aria-label $165
cmp-daily-histogram-bars-legend-max-price-aria-label $334
Displaying fares for November-2026
  • MDW–LGA, 11/13/2026: From $245
    13

    Fri

    NOV

  • MDW–LGA, 11/14/2026: From $240
    14

    Sat

  • MDW–LGA, 11/15/2026: From $240
    15

    Sun

  • MDW–LGA, 11/16/2026: From $235
    16

    Mon

  • MDW–LGA, 11/17/2026: From $240
    17

    Tue

  • MDW–LGA, 11/18/2026: From $240
    18

    Wed

  • MDW–LGA, 11/19/2026: From $240
    19

    Thu

  • MDW–LGA, 11/20/2026: From $240
    20

    Fri

  • MDW–LGA, 11/21/2026: From $240
    21

    Sat

  • MDW–LGA, 11/22/2026: From $240
    22

    Sun

  • MDW–LGA, 11/23/2026: From $240
    23

    Mon

  • MDW–LGA, 11/24/2026: From $235
    24

    Tue

  • MDW–LGA, 11/25/2026: From $240
    25

    Wed

  • MDW–LGA, 11/26/2026: From $240
    26

    Thu

  • MDW–LGA, 11/27/2026: From $218
    27

    Fri

  • MDW–LGA, 11/28/2026: From $259
    28

    Sat

  • MDW–LGA, 11/29/2026: From $334
    29

    Sun

  • MDW–LGA, 11/30/2026: From $288
    30

    Mon

  • MDW–LGA, 12/01/2026: From $218
    01

    Tue

    DEC

  • MDW–LGA, 12/02/2026: From $218
    02

    Wed

  • MDW–LGA, 12/03/2026: From $218
    03

    Thu

  • MDW–LGA, 12/04/2026: From $205
    04

    Fri

  • MDW–LGA, 12/05/2026: From $189
    05

    Sat

  • MDW–LGA, 12/06/2026: From $174
    06

    Sun

  • MDW–LGA, 12/07/2026: From $174
    07

    Mon

  • MDW–LGA, 12/08/2026: From $165
    08

    Tue

  • MDW–LGA, 12/09/2026: From $165
    09

    Wed

  • MDW–LGA, 12/10/2026: From $174
    10

    Thu

  • MDW–LGA, 12/11/2026: From $194
    11

    Fri

  • MDW–LGA, 12/12/2026: From $189
    12

    Sat

  • Range$165-$334

    Flight Details

    Departing from:
    Chicago Midway International Airport
    Arriving at:
    La Guardia Airport
    Average flight time:
    2 hours 2 minutes
    Distance:
    725 miles

    Explore New York (LaGuardia)

    The city that never sleeps is full of amazing sights and sounds. Maybe you can squeeze a Broadway show into your itinerary, or spend time at the Metropolitan Museum of Art—the largest art museum in the United States. Consider exploring Ellis Island to learn about a very different type of travel experience! Climb the Statue of Liberty and admire the view. See the magnificent architecture of Gotham's skyscrapers for yourself, from the Empire State Building to the Flatiron or the Chrysler Building. These iconic sights can be accompanied by world-class restaurants and eateries or a simple slice of New York-style pizza—it's up to you!

    New York City is one of the United States' great centers for culture and art. Whether you're interested in musicals, opera, ballet, or rock concerts, the Big Apple has it all. Award-winning shows are a constant feature of the New York arts scene. Get tickets for Shakespeare plays, the ballet, the hottest musicals, and more. From classical to modern, dramas to comedies, New York City has something for everyone.

    Questions we hear the most

    The average flight time from Chicago (Midway) to New York (LaGuardia) is 2 hours 2 minutes.
    There are 157 weekly flights from Chicago (Midway) to New York (LaGuardia) on Southwest Airlines.
    Yes, Southwest flies nonstop from Chicago (Midway) to New York (LaGuardia) 7 times per day from Monday through Friday.
    Yes, Southwest flies nonstop from Chicago (Midway) to New York (LaGuardia) 4 times per day on Saturdays and 7 times per day on Sundays.
    To find the lowest fares by day and time to fly Chicago (Midway) to New York (LaGuardia) with Southwest, check out our Low Fare Calendar.
    You can rent a car at La Guardia Airport book yours with your flight.
    Yes! Flights from Chicago (Midway) to New York (LaGuardia)—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.

    Popular Flights from Chicago-Midway