Southwest® flights from Chicago-Midway to Philadelphia from $129

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Low fares from Chicago-Midway to Philadelphia

$

Chicago-Midway (MDW)to

Philadelphia (PHL)
Depart: 11/10/2026

One-way

Basic

From
$129
Seen: 23 hrs ago

Chicago-Midway (MDW)to

Philadelphia (PHL)
Depart: 10/26/2026

One-way

Basic

From
$129
Seen: 18 hrs ago

Chicago-Midway (MDW)to

Philadelphia (PHL)
Depart: 10/31/2026

One-way

Basic

From
$129
Seen: 3 hrs ago

Chicago-Midway (MDW)to

Philadelphia (PHL)
Depart: 12/24/2026

One-way

Basic

From
$129
Seen: 15 hrs ago

Chicago-Midway (MDW)to

Philadelphia (PHL)
Depart: 12/02/2026

One-way

Basic

From
$129
Seen: 6 hrs ago

Chicago-Midway (MDW)to

Philadelphia (PHL)
Depart: 11/05/2026

One-way

Basic

From
$129
Seen: 17 hrs ago

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Explore flights from Chicago-Midway to Philadelphia

Oct 2026
From$129*
Seen: 3 hrs ago
One Way/Basic
Nov 2026
From$129*
Seen: 17 hrs ago
One Way/Basic
Dec 2026
From$129*
Seen: 5 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $129
cmp-daily-histogram-bars-legend-max-price-aria-label $275
Displaying fares for October-2026
  • MDW–PHL: cmp-view-offers-disclaimer. Find Offers
    02

    Fri

    OCT

  • MDW–PHL, 10/03/2026: From $198
    03

    Sat

  • MDW–PHL, 10/04/2026: From $242
    04

    Sun

  • MDW–PHL, 10/05/2026: From $242
    05

    Mon

  • MDW–PHL, 10/06/2026: From $198
    06

    Tue

  • MDW–PHL, 10/07/2026: From $208
    07

    Wed

  • MDW–PHL, 10/08/2026: From $275
    08

    Thu

  • MDW–PHL, 10/09/2026: From $242
    09

    Fri

  • MDW–PHL, 10/10/2026: From $198
    10

    Sat

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

    Sun

  • MDW–PHL, 10/12/2026: From $267
    12

    Mon

  • MDW–PHL, 10/13/2026: From $238
    13

    Tue

  • MDW–PHL, 10/14/2026: From $198
    14

    Wed

  • MDW–PHL, 10/15/2026: From $242
    15

    Thu

  • MDW–PHL, 10/16/2026: From $242
    16

    Fri

  • MDW–PHL: cmp-view-offers-disclaimer. Find Offers
    17

    Sat

  • MDW–PHL, 10/18/2026: From $242
    18

    Sun

  • MDW–PHL, 10/19/2026: From $242
    19

    Mon

  • MDW–PHL, 10/20/2026: From $198
    20

    Tue

  • MDW–PHL: cmp-view-offers-disclaimer. Find Offers
    21

    Wed

  • MDW–PHL, 10/22/2026: From $242
    22

    Thu

  • MDW–PHL, 10/23/2026: From $138
    23

    Fri

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

    Sat

  • MDW–PHL, 10/25/2026: From $156
    25

    Sun

  • MDW–PHL, 10/26/2026: From $129
    26

    Mon

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

    Tue

  • MDW–PHL, 10/28/2026: From $156
    28

    Wed

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

    Thu

  • MDW–PHL, 10/30/2026: From $156
    30

    Fri

  • MDW–PHL, 10/31/2026: From $129
    31

    Sat

  • MDW–PHL, 11/01/2026: From $156
    01

    Sun

    NOV

    • Range$129-$275

    *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

    Route Information

    119† Weekly flights
    • 4‡ Nonstop flights per day Monday through Friday
    • 3‡ Nonstop flights on Saturday
    • 5‡ Nonstop flights on Sunday

    † 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

    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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