Southwest® flights from Philadelphia to Chicago-Midway from $105

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Low fares from Philadelphia to Chicago-Midway

$

Philadelphia (PHL)to

Chicago-Midway (MDW)
Depart: 02/06/2027

One-way

Basic

From
$105
Seen: 1 hour ago

Philadelphia (PHL)to

Chicago-Midway (MDW)
Depart: 12/16/2026

One-way

Basic

From
$105
Seen: 18 hrs ago

Philadelphia (PHL)to

Chicago-Midway (MDW)
Depart: 12/15/2026

One-way

Basic

From
$105
Seen: 4 hrs ago

Philadelphia (PHL)to

Chicago-Midway (MDW)
Depart: 02/17/2027

One-way

Basic

From
$105
Seen: 17 hrs ago

Philadelphia (PHL)to

Chicago-Midway (MDW)
Depart: 01/06/2027

One-way

Basic

From
$105
Seen: 1 hour ago

Philadelphia (PHL)to

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

One-way

Basic

From
$140
Seen: 16 hrs ago

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Explore flights from Philadelphia to Chicago-Midway

Nov 2026
From$213*
Seen: 9 hrs ago
One Way/Basic
Dec 2026
From$105*
Seen: 18 hrs ago
One Way/Basic
Jan 2027
From$105*
Seen: 1 hour ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $140
cmp-daily-histogram-bars-legend-max-price-aria-label $415
Displaying fares for November-2026
  • PHL–MDW, 11/10/2026: From $213
    10

    Tue

    NOV

  • PHL–MDW, 11/11/2026: From $213
    11

    Wed

  • PHL–MDW, 11/12/2026: From $257
    12

    Thu

  • PHL–MDW, 11/13/2026: From $257
    13

    Fri

  • PHL–MDW, 11/14/2026: From $213
    14

    Sat

  • PHL–MDW, 11/15/2026: From $290
    15

    Sun

  • PHL–MDW, 11/16/2026: From $257
    16

    Mon

  • PHL–MDW, 11/17/2026: From $213
    17

    Tue

  • PHL–MDW, 11/18/2026: From $213
    18

    Wed

  • PHL–MDW, 11/19/2026: From $257
    19

    Thu

  • PHL–MDW, 11/20/2026: From $295
    20

    Fri

  • PHL–MDW, 11/21/2026: From $213
    21

    Sat

  • PHL–MDW, 11/22/2026: From $257
    22

    Sun

  • PHL–MDW, 11/23/2026: From $257
    23

    Mon

  • PHL–MDW, 11/24/2026: From $213
    24

    Tue

  • PHL–MDW, 11/25/2026: From $213
    25

    Wed

  • PHL–MDW: cmp-view-offers-disclaimer. Find Offers
    26

    Thu

  • PHL–MDW, 11/27/2026: From $257
    27

    Fri

  • PHL–MDW, 11/28/2026: From $415
    28

    Sat

  • PHL–MDW, 11/29/2026: From $372
    29

    Sun

  • PHL–MDW, 11/30/2026: From $267
    30

    Mon

  • PHL–MDW, 12/01/2026: From $150
    01

    Tue

    DEC

  • PHL–MDW, 12/02/2026: From $140
    02

    Wed

  • PHL–MDW, 12/03/2026: From $155
    03

    Thu

  • PHL–MDW, 12/04/2026: From $165
    04

    Fri

  • PHL–MDW, 12/05/2026: From $140
    05

    Sat

  • PHL–MDW, 12/06/2026: From $257
    06

    Sun

  • PHL–MDW, 12/07/2026: From $155
    07

    Mon

  • PHL–MDW, 12/08/2026: From $140
    08

    Tue

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

    Wed

    • Range$140-$415

    *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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