Southwest® flights from Philadelphia to Chicago (Midway) from $129

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Low fares from Philadelphia to Chicago (Midway)

$

Philadelphia (PHL)to

Chicago (Midway) (MDW)
Depart: 09/05/2026

One-way

Basic

From
$129
Seen: 23 hrs ago

Philadelphia (PHL)to

Chicago (Midway) (MDW)
Depart: 09/06/2026

One-way

Basic

From
$129
Seen: 21 hrs ago

Philadelphia (PHL)to

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

One-way

Basic

From
$129
Seen: 10 hrs ago

Philadelphia (PHL)to

Chicago (Midway) (MDW)
Depart: 09/19/2026

One-way

Basic

From
$140
Seen: 22 hrs ago

Philadelphia (PHL)to

Chicago (Midway) (MDW)
Depart: 09/30/2026

One-way

Basic

From
$140
Seen: 8 hrs ago

Philadelphia (PHL)to

Chicago (Midway) (MDW)
Depart: 09/02/2026

One-way

Basic

From
$140
Seen: 7 hrs ago

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Explore flights from Philadelphia to Chicago (Midway)

Aug 2026
From$140*
Seen: 2 hrs ago
One Way/Basic
Sep 2026
From$129*
Seen: 23 hrs ago
One Way/Basic
Oct 2026
From$140*
Seen: 8 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $140
cmp-daily-histogram-bars-legend-max-price-aria-label $273
Displaying fares for August-2026
  • PHL–MDW: cmp-view-offers-disclaimer. Find Offers
    01

    Sat

    AUG

  • PHL–MDW, 08/02/2026: From $273
    02

    Sun

  • PHL–MDW, 08/03/2026: From $273
    03

    Mon

  • PHL–MDW, 08/04/2026: From $220
    04

    Tue

  • PHL–MDW, 08/05/2026: From $220
    05

    Wed

  • PHL–MDW, 08/06/2026: From $273
    06

    Thu

  • PHL–MDW, 08/07/2026: From $273
    07

    Fri

  • PHL–MDW, 08/08/2026: From $251
    08

    Sat

  • PHL–MDW: cmp-view-offers-disclaimer. Find Offers
    09

    Sun

  • PHL–MDW, 08/10/2026: From $273
    10

    Mon

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

    Tue

  • PHL–MDW, 08/12/2026: From $220
    12

    Wed

  • PHL–MDW, 08/13/2026: From $273
    13

    Thu

  • PHL–MDW, 08/14/2026: From $246
    14

    Fri

  • PHL–MDW, 08/15/2026: From $220
    15

    Sat

  • PHL–MDW, 08/16/2026: From $246
    16

    Sun

  • PHL–MDW, 08/17/2026: From $246
    17

    Mon

  • PHL–MDW, 08/18/2026: From $220
    18

    Tue

  • PHL–MDW, 08/19/2026: From $220
    19

    Wed

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

    Thu

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

    Fri

  • PHL–MDW, 08/22/2026: From $140
    22

    Sat

  • PHL–MDW: cmp-view-offers-disclaimer. Find Offers
    23

    Sun

  • PHL–MDW, 08/24/2026: From $140
    24

    Mon

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

    Tue

  • PHL–MDW, 08/26/2026: From $140
    26

    Wed

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

    Thu

  • PHL–MDW, 08/28/2026: From $177
    28

    Fri

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

    Sat

  • PHL–MDW, 08/30/2026: From $203
    30

    Sun

  • PHL–MDW: cmp-view-offers-disclaimer. Find Offers
    31

    Mon

    • Range$140-$273

    *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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