Southwest® flights from Philadelphia to Chicago (O'Hare)

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Low fares from Philadelphia to Chicago (O'Hare)

$

Philadelphia (PHL)to

Chicago (Midway) (MDW)
Depart: 10/30/2026

One-way

Basic

From
$129
Seen: 10 hrs ago

Philadelphia (PHL)to

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

One-way

Basic

From
$139
Seen: 12 hrs ago

Philadelphia (PHL)to

Chicago (Midway) (MDW)
Depart: 10/26/2026

One-way

Basic

From
$140
Seen: 20 hrs ago

Philadelphia (PHL)to

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

One-way

Basic

From
$140
Seen: 18 hrs ago

Philadelphia (PHL)to

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

One-way

Basic

From
$140
Seen: 20 hrs ago

Philadelphia (PHL)to

Chicago (Midway) (MDW)
Depart: 08/29/2026

One-way

Basic

From
$140
Seen: 10 hrs ago

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Explore flights from Philadelphia to Chicago (O'Hare)

Aug 2026
From$140*
Seen: 10 hrs ago
One Way/Basic
Sep 2026
From$139*
Seen: 12 hrs ago
One Way/Basic
Oct 2026
From$129*
Seen: 10 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, 08/05/2026: From $220
    05

    Wed

    AUG

  • 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, 08/09/2026: From $273
    09

    Sun

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

    Mon

  • PHL–MDW, 08/11/2026: From $220
    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 $273
    14

    Fri

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

    Sat

  • PHL–MDW, 08/16/2026: From $273
    16

    Sun

  • PHL–MDW, 08/17/2026: From $273
    17

    Mon

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

    Tue

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

    Wed

  • PHL–MDW, 08/20/2026: From $246
    20

    Thu

  • PHL–MDW, 08/21/2026: From $246
    21

    Fri

  • PHL–MDW, 08/22/2026: From $220
    22

    Sat

  • PHL–MDW, 08/23/2026: From $246
    23

    Sun

  • PHL–MDW, 08/24/2026: From $246
    24

    Mon

  • PHL–MDW, 08/25/2026: From $140
    25

    Tue

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

    Wed

  • PHL–MDW, 08/27/2026: From $140
    27

    Thu

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

    Fri

  • PHL–MDW, 08/29/2026: From $140
    29

    Sat

  • PHL–MDW: cmp-view-offers-disclaimer. Find Offers
    30

    Sun

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

    Mon

  • PHL–MDW, 09/01/2026: From $140
    01

    Tue

    SEP

  • PHL–MDW, 09/02/2026: From $140
    02

    Wed

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

    Thu

  • PHL–MDW, 09/04/2026: From $177
    04

    Fri

    • 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:
    O'Hare International Airport
    Distance:
    678 miles

    Route Information

    32† Weekly flights

    † 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

    There are 32 weekly flights from Philadelphia to Chicago (O'Hare) on Southwest Airlines.
    To find the lowest fares by day and time to fly Philadelphia to Chicago (O'Hare) with Southwest, check out our Low Fare Calendar.
    You can rent a car at O'Hare International Airport book yours with your flight.
    Yes! Flights from Philadelphia to Chicago (O'Hare)—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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