Southwest® flights from Philadelphia to Chicago-Midway from $83

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Low fares from Philadelphia to Chicago-Midway

$

Philadelphia (PHL)to

Chicago-Midway (MDW)
Depart: 11/10/2026

One-way

Basic

From
$83
Seen: 23 hrs ago

Philadelphia (PHL)to

Chicago-Midway (MDW)
Depart: 12/03/2026

One-way

Basic

From
$83
Seen: 15 hrs ago

Philadelphia (PHL)to

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

One-way

Basic

From
$83
Seen: 20 hrs ago

Philadelphia (PHL)to

Chicago-Midway (MDW)
Depart: 11/13/2026

One-way

Basic

From
$83
Seen: 14 hrs ago

Philadelphia (PHL)to

Chicago-Midway (MDW)
Depart: 12/25/2026

One-way

Basic

From
$83
Seen: 6 hrs ago

Philadelphia (PHL)to

Chicago-Midway (MDW)
Depart: 12/05/2026

One-way

Basic

From
$83
Seen: 5 hrs ago

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Explore flights from Philadelphia to Chicago-Midway

Oct 2026
From$208*
Seen: 22 hrs ago
One Way/Basic
Nov 2026
From$83*
Seen: 23 hrs ago
One Way/Basic
Dec 2026
From$83*
Seen: 10 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $83
cmp-daily-histogram-bars-legend-max-price-aria-label $252
Displaying fares for October-2026
  • PHL–MDW, 10/21/2026: From $208
    21

    Wed

    OCT

  • PHL–MDW, 10/22/2026: From $252
    22

    Thu

  • PHL–MDW, 10/23/2026: From $252
    23

    Fri

  • PHL–MDW, 10/24/2026: From $208
    24

    Sat

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

    Sun

  • PHL–MDW, 10/26/2026: From $252
    26

    Mon

  • PHL–MDW, 10/27/2026: From $218
    27

    Tue

  • PHL–MDW, 10/28/2026: From $218
    28

    Wed

  • PHL–MDW, 10/29/2026: From $252
    29

    Thu

  • PHL–MDW, 10/30/2026: From $252
    30

    Fri

  • PHL–MDW, 10/31/2026: From $208
    31

    Sat

  • PHL–MDW, 11/01/2026: From $252
    01

    Sun

    NOV

  • PHL–MDW, 11/02/2026: From $252
    02

    Mon

  • PHL–MDW: cmp-view-offers-disclaimer. Find Offers
    03

    Tue

  • PHL–MDW, 11/04/2026: From $208
    04

    Wed

  • PHL–MDW, 11/05/2026: From $252
    05

    Thu

  • PHL–MDW, 11/06/2026: From $252
    06

    Fri

  • PHL–MDW, 11/07/2026: From $208
    07

    Sat

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

    Sun

  • PHL–MDW, 11/09/2026: From $83
    09

    Mon

  • PHL–MDW, 11/10/2026: From $83
    10

    Tue

  • PHL–MDW, 11/11/2026: From $83
    11

    Wed

  • PHL–MDW, 11/12/2026: From $83
    12

    Thu

  • PHL–MDW, 11/13/2026: From $83
    13

    Fri

  • PHL–MDW, 11/14/2026: From $83
    14

    Sat

  • PHL–MDW, 11/15/2026: From $106
    15

    Sun

  • PHL–MDW, 11/16/2026: From $252
    16

    Mon

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

    Tue

  • PHL–MDW, 11/18/2026: From $83
    18

    Wed

  • PHL–MDW, 11/19/2026: From $83
    19

    Thu

  • PHL–MDW, 11/20/2026: From $157
    20

    Fri

    • Range$83-$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

    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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