Southwest® flights from Chicago-Midway to Philadelphia from $119

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Low fares from Chicago-Midway to Philadelphia

$

Chicago-Midway (MDW)to

Philadelphia (PHL)
Depart: 11/17/2026

One-way

Basic

From
$119
Seen: 22 hrs ago

Chicago-Midway (MDW)to

Philadelphia (PHL)
Depart: 11/11/2026

One-way

Basic

From
$145
Seen: 21 hrs ago

Chicago-Midway (MDW)to

Philadelphia (PHL)
Depart: 12/12/2026

One-way

Basic

From
$145
Seen: 19 hrs ago

Chicago-Midway (MDW)to

Philadelphia (PHL)
Depart: 10/31/2026

One-way

Basic

From
$145
Seen: 11 hrs ago

Chicago-Midway (MDW)to

Philadelphia (PHL)
Depart: 10/27/2026

One-way

Basic

From
$145
Seen: 15 hrs ago

Chicago-Midway (MDW)to

Philadelphia (PHL)
Depart: 12/02/2026

One-way

Basic

From
$145
Seen: 5 hrs ago

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Explore flights from Chicago-Midway to Philadelphia

Sep 2026
From$198*
Seen: 5 hrs ago
One Way/Basic
Oct 2026
From$145*
Seen: 19 hrs ago
One Way/Basic
Nov 2026
From$119*
Seen: 22 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $156
cmp-daily-histogram-bars-legend-max-price-aria-label $393
Displaying fares for September-2026
  • MDW–PHL, 09/12/2026: From $198
    12

    Sat

    SEP

  • MDW–PHL, 09/13/2026: From $393
    13

    Sun

  • MDW–PHL, 09/14/2026: From $242
    14

    Mon

  • MDW–PHL, 09/15/2026: From $198
    15

    Tue

  • MDW–PHL, 09/16/2026: From $198
    16

    Wed

  • MDW–PHL, 09/17/2026: From $242
    17

    Thu

  • MDW–PHL, 09/18/2026: From $242
    18

    Fri

  • MDW–PHL, 09/19/2026: From $198
    19

    Sat

  • MDW–PHL: cmp-view-offers-disclaimer. Find Offers
    20

    Sun

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

    Mon

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

    Tue

  • MDW–PHL, 09/23/2026: From $198
    23

    Wed

  • MDW–PHL, 09/24/2026: From $252
    24

    Thu

  • MDW–PHL, 09/25/2026: From $242
    25

    Fri

  • MDW–PHL, 09/26/2026: From $198
    26

    Sat

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

    Sun

  • MDW–PHL, 09/28/2026: From $242
    28

    Mon

  • MDW–PHL, 09/29/2026: From $260
    29

    Tue

  • MDW–PHL: cmp-view-offers-disclaimer. Find Offers
    30

    Wed

  • MDW–PHL, 10/01/2026: From $242
    01

    Thu

    OCT

  • MDW–PHL, 10/02/2026: From $156
    02

    Fri

  • MDW–PHL, 10/03/2026: From $156
    03

    Sat

  • MDW–PHL, 10/04/2026: From $156
    04

    Sun

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

    Mon

  • MDW–PHL, 10/06/2026: From $156
    06

    Tue

  • MDW–PHL, 10/07/2026: From $156
    07

    Wed

  • MDW–PHL: cmp-view-offers-disclaimer. Find Offers
    08

    Thu

  • MDW–PHL, 10/09/2026: From $156
    09

    Fri

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

    Sat

  • MDW–PHL, 10/11/2026: From $156
    11

    Sun

    • Range$156-$393

    *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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