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

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Low fares from Philadelphia to Chicago-Midway

$

Philadelphia (PHL)to

Chicago-Midway (MDW)
Depart: 11/05/2026

One-way

Basic

From
$119
Seen: 17 hrs ago

Philadelphia (PHL)to

Chicago-Midway (MDW)
Depart: 12/10/2026

One-way

Basic

From
$119
Seen: 16 hrs ago

Philadelphia (PHL)to

Chicago-Midway (MDW)
Depart: 10/22/2026

One-way

Basic

From
$119
Seen: 10 hrs ago

Philadelphia (PHL)to

Chicago-Midway (MDW)
Depart: 11/09/2026

One-way

Basic

From
$119
Seen: 1 hour ago

Philadelphia (PHL)to

Chicago-Midway (MDW)
Depart: 11/18/2026

One-way

Basic

From
$119
Seen: 1 hour ago

Philadelphia (PHL)to

Chicago-Midway (MDW)
Depart: 11/07/2026

One-way

Basic

From
$119
Seen: 4 hrs ago

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Explore flights from Philadelphia to Chicago-Midway

Sep 2026
From$198*
Seen: 2 hrs ago
One Way/Basic
Oct 2026
From$119*
Seen: 11 hrs ago
One Way/Basic
Nov 2026
From$119*
Seen: 3 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $119
cmp-daily-histogram-bars-legend-max-price-aria-label $293
Displaying fares for September-2026
  • PHL–MDW, 09/11/2026: From $242
    11

    Fri

    SEP

  • PHL–MDW, 09/12/2026: From $198
    12

    Sat

  • PHL–MDW, 09/13/2026: From $242
    13

    Sun

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

    Mon

  • PHL–MDW, 09/15/2026: From $240
    15

    Tue

  • PHL–MDW, 09/16/2026: From $240
    16

    Wed

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

    Thu

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

    Fri

  • PHL–MDW: cmp-view-offers-disclaimer. Find Offers
    19

    Sat

  • PHL–MDW, 09/20/2026: From $293
    20

    Sun

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

    Mon

  • PHL–MDW, 09/22/2026: From $275
    22

    Tue

  • PHL–MDW, 09/23/2026: From $240
    23

    Wed

  • PHL–MDW, 09/24/2026: From $256
    24

    Thu

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

    Fri

  • PHL–MDW, 09/26/2026: From $240
    26

    Sat

  • PHL–MDW, 09/27/2026: From $256
    27

    Sun

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

    Mon

  • PHL–MDW, 09/29/2026: From $240
    29

    Tue

  • PHL–MDW, 09/30/2026: From $240
    30

    Wed

  • PHL–MDW, 10/01/2026: From $128
    01

    Thu

    OCT

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

    Fri

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

    Sat

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

    Sun

  • PHL–MDW, 10/05/2026: From $156
    05

    Mon

  • PHL–MDW, 10/06/2026: From $119
    06

    Tue

  • PHL–MDW, 10/07/2026: From $119
    07

    Wed

  • PHL–MDW, 10/08/2026: From $119
    08

    Thu

  • PHL–MDW, 10/09/2026: From $216
    09

    Fri

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

    Sat

    • Range$119-$293

    *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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