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

Promo Code

Low fares from Philadelphia to Chicago-Midway

$

Philadelphia (PHL)to

Chicago-Midway (MDW)
Depart: 11/04/2026

One-way

Basic

From
$129
Seen: 13 hrs ago

Philadelphia (PHL)to

Chicago-Midway (MDW)
Depart: 12/08/2026

One-way

Basic

From
$129
Seen: 3 hrs ago

Philadelphia (PHL)to

Chicago-Midway (MDW)
Depart: 11/12/2026

One-way

Basic

From
$129
Seen: 6 hrs ago

Philadelphia (PHL)to

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

One-way

Basic

From
$129
Seen: 3 hrs ago

Philadelphia (PHL)to

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

One-way

Basic

From
$129
Seen: 9 hrs ago

Philadelphia (PHL)to

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

One-way

Basic

From
$129
Seen: 12 hrs ago

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Explore flights from Philadelphia to Chicago-Midway

Oct 2026
From$129*
Seen: 8 hrs ago
One Way/Basic
Nov 2026
From$129*
Seen: 9 hrs ago
One Way/Basic
Dec 2026
From$129*
Seen: 21 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $129
cmp-daily-histogram-bars-legend-max-price-aria-label $252
Displaying fares for October-2026
  • PHL–MDW, 10/01/2026: From $242
    01

    Thu

    OCT

  • PHL–MDW, 10/02/2026: From $242
    02

    Fri

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

    Sat

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

    Sun

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

    Mon

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

    Tue

  • PHL–MDW, 10/07/2026: From $198
    07

    Wed

  • PHL–MDW, 10/08/2026: From $242
    08

    Thu

  • PHL–MDW, 10/09/2026: From $252
    09

    Fri

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

    Sat

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

    Sun

  • PHL–MDW: cmp-view-offers-disclaimer. Find Offers
    12

    Mon

  • PHL–MDW, 10/13/2026: From $198
    13

    Tue

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

    Wed

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

    Thu

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

    Fri

  • PHL–MDW, 10/17/2026: From $198
    17

    Sat

  • PHL–MDW: cmp-view-offers-disclaimer. Find Offers
    18

    Sun

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

    Mon

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

    Tue

  • PHL–MDW, 10/21/2026: From $129
    21

    Wed

  • PHL–MDW, 10/22/2026: From $129
    22

    Thu

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

    Fri

  • PHL–MDW, 10/24/2026: From $129
    24

    Sat

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

    Sun

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

    Mon

  • PHL–MDW, 10/27/2026: From $138
    27

    Tue

  • PHL–MDW, 10/28/2026: From $138
    28

    Wed

  • PHL–MDW, 10/29/2026: From $129
    29

    Thu

  • PHL–MDW, 10/30/2026: From $138
    30

    Fri

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

    Sat

    • Range$129-$252

    *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:
    Philadelphia International Airport
    Arriving at:
    Chicago Midway International Airport
    Average flight time:
    2 hours 7 minutes
    Distance:
    668 miles

    Route Information

    145† 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 Philadelphia to Chicago (Midway) is 2 hours 7 minutes.
    There are 145 weekly flights from Philadelphia to Chicago (Midway) on Southwest Airlines.
    Yes, Southwest flies nonstop from Philadelphia to Chicago (Midway) 4 times per day from Monday through Friday.
    Yes, Southwest flies nonstop from Philadelphia to Chicago (Midway) 3 times per day on Saturdays and 5 times per day on Sundays.
    To find the lowest fares by day and time to fly Philadelphia to Chicago (Midway) with Southwest, check out our Low Fare Calendar.
    You can rent a car at Chicago Midway International Airport book yours with your flight.
    Yes! Flights from Philadelphia to Chicago (Midway)—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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