Southwest® flights from Chicago-Midway to Philadelphia from $105

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Low fares from Chicago-Midway to Philadelphia

$

Chicago-Midway (MDW)to

Philadelphia (PHL)
Depart: 12/12/2026

One-way

Basic

From
$105
Seen: 11 hrs ago

Chicago-Midway (MDW)to

Philadelphia (PHL)
Depart: 12/16/2026

One-way

Basic

From
$105
Seen: 23 hrs ago

Chicago-Midway (MDW)to

Philadelphia (PHL)
Depart: 01/09/2027

One-way

Basic

From
$105
Seen: 12 hrs ago

Chicago-Midway (MDW)to

Philadelphia (PHL)
Depart: 01/16/2027

One-way

Basic

From
$105
Seen: 6 hrs ago

Chicago-Midway (MDW)to

Philadelphia (PHL)
Depart: 01/11/2027

One-way

Basic

From
$145
Seen: 17 hrs ago

Chicago-Midway (MDW)to

Philadelphia (PHL)
Depart: 01/14/2027

One-way

Basic

From
$145
Seen: 11 hrs ago

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Explore flights from Chicago-Midway to Philadelphia

Nov 2026
From$213*
Seen: 18 hrs ago
One Way/Basic
Dec 2026
From$105*
Seen: 23 hrs ago
One Way/Basic
Jan 2027
From$105*
Seen: 12 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $145
cmp-daily-histogram-bars-legend-max-price-aria-label $385
Displaying fares for November-2026
  • MDW–PHL, 11/12/2026: From $257
    12

    Thu

    NOV

  • MDW–PHL, 11/13/2026: From $257
    13

    Fri

  • MDW–PHL, 11/14/2026: From $213
    14

    Sat

  • MDW–PHL, 11/15/2026: From $272
    15

    Sun

  • MDW–PHL, 11/16/2026: From $267
    16

    Mon

  • MDW–PHL, 11/17/2026: From $213
    17

    Tue

  • MDW–PHL, 11/18/2026: From $250
    18

    Wed

  • MDW–PHL, 11/19/2026: From $385
    19

    Thu

  • MDW–PHL, 11/20/2026: From $330
    20

    Fri

  • MDW–PHL, 11/21/2026: From $234
    21

    Sat

  • MDW–PHL, 11/22/2026: From $295
    22

    Sun

  • MDW–PHL, 11/23/2026: From $257
    23

    Mon

  • MDW–PHL, 11/24/2026: From $240
    24

    Tue

  • MDW–PHL: cmp-view-offers-disclaimer. Find Offers
    25

    Wed

  • MDW–PHL, 11/26/2026: From $257
    26

    Thu

  • MDW–PHL, 11/27/2026: From $257
    27

    Fri

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

    Sat

  • MDW–PHL: cmp-view-offers-disclaimer. Find Offers
    29

    Sun

  • MDW–PHL, 11/30/2026: From $257
    30

    Mon

  • MDW–PHL, 12/01/2026: From $213
    01

    Tue

    DEC

  • MDW–PHL, 12/02/2026: From $145
    02

    Wed

  • MDW–PHL, 12/03/2026: From $237
    03

    Thu

  • MDW–PHL, 12/04/2026: From $180
    04

    Fri

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

    Sat

  • MDW–PHL, 12/06/2026: From $257
    06

    Sun

  • MDW–PHL, 12/07/2026: From $165
    07

    Mon

  • MDW–PHL, 12/08/2026: From $145
    08

    Tue

  • MDW–PHL, 12/09/2026: From $145
    09

    Wed

  • MDW–PHL, 12/10/2026: From $165
    10

    Thu

  • MDW–PHL, 12/11/2026: From $145
    11

    Fri

    • Range$145-$385

    *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:
    Chicago Midway International Airport
    Arriving at:
    Philadelphia International Airport
    Average flight time:
    1 hour 54 minutes
    Distance:
    668 miles

    Questions we hear the most

    The average flight time from Chicago (Midway) to Philadelphia is 1 hour 54 minutes.
    There are 119 weekly flights from Chicago (Midway) to Philadelphia on Southwest Airlines.
    Yes, Southwest flies nonstop from Chicago (Midway) to Philadelphia 4 times per day from Monday through Friday.
    Yes, Southwest flies nonstop from Chicago (Midway) to Philadelphia 3 times per day on Saturdays and 5 times per day on Sundays.
    To find the lowest fares by day and time to fly Chicago (Midway) to Philadelphia with Southwest, check out our Low Fare Calendar.
    You can rent a car at Philadelphia International Airport book yours with your flight.
    Yes! Flights from Chicago (Midway) to Philadelphia—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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