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

Promo Code

Low fares from Chicago-Midway to Philadelphia

$

Chicago-Midway (MDW)to

Philadelphia (PHL)
Depart: 01/22/2027

One-way

Basic

From
$83
Seen: 22 hrs ago

Chicago-Midway (MDW)to

Philadelphia (PHL)
Depart: 11/17/2026

One-way

Basic

From
$83
Seen: 11 hrs ago

Chicago-Midway (MDW)to

Philadelphia (PHL)
Depart: 11/10/2026

One-way

Basic

From
$83
Seen: 18 hrs ago

Chicago-Midway (MDW)to

Philadelphia (PHL)
Depart: 12/11/2026

One-way

Basic

From
$83
Seen: 19 hrs ago

Chicago-Midway (MDW)to

Philadelphia (PHL)
Depart: 12/15/2026

One-way

Basic

From
$83
Seen: 16 hrs ago

Chicago-Midway (MDW)to

Philadelphia (PHL)
Depart: 11/27/2026

One-way

Basic

From
$83
Seen: 4 hrs ago

Looking for more low-fare flights?

Check out the Low Fare Calendar to find a fare that works for you. Just choose the month you want to depart and return, and we’ll show you the best fares available.

Find low fares

Explore flights from Chicago-Midway to Philadelphia

Oct 2026
From$208*
Seen: 6 hrs ago
One Way/Basic
Nov 2026
From$83*
Seen: 18 hrs ago
One Way/Basic
Dec 2026
From$83*
Seen: 7 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $83
cmp-daily-histogram-bars-legend-max-price-aria-label $334
Displaying fares for October-2026
  • MDW–PHL, 10/23/2026: From $252
    23

    Fri

    OCT

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

    Sat

  • MDW–PHL, 10/25/2026: From $252
    25

    Sun

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

    Mon

  • MDW–PHL, 10/27/2026: From $208
    27

    Tue

  • MDW–PHL, 10/28/2026: From $208
    28

    Wed

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

    Thu

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

    Fri

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

    Sat

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

    Sun

    NOV

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

    Mon

  • MDW–PHL, 11/03/2026: From $208
    03

    Tue

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

    Wed

  • MDW–PHL: cmp-view-offers-disclaimer. Find Offers
    05

    Thu

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

    Fri

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

    Sat

  • MDW–PHL, 11/08/2026: From $319
    08

    Sun

  • MDW–PHL, 11/09/2026: From $252
    09

    Mon

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

    Tue

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

    Wed

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

    Thu

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

    Fri

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

    Sat

  • MDW–PHL: cmp-view-offers-disclaimer. Find Offers
    15

    Sun

  • MDW–PHL: cmp-view-offers-disclaimer. Find Offers
    16

    Mon

  • MDW–PHL, 11/17/2026: From $83
    17

    Tue

  • MDW–PHL, 11/18/2026: From $131
    18

    Wed

  • MDW–PHL, 11/19/2026: From $307
    19

    Thu

  • MDW–PHL, 11/20/2026: From $334
    20

    Fri

  • MDW–PHL, 11/21/2026: From $246
    21

    Sat

  • MDW–PHL, 11/22/2026: From $192
    22

    Sun

    • Range$83-$334

    *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:
    Chicago Midway International Airport
    Arriving at:
    Philadelphia International Airport
    Average flight time:
    1 hour 54 minutes
    Distance:
    668 miles

    Questions we hear the most

    The average flight time from Chicago (Midway) to Philadelphia is 1 hour 54 minutes.
    There are 119 weekly flights from Chicago (Midway) to Philadelphia on Southwest Airlines.
    Yes, Southwest flies nonstop from Chicago (Midway) to Philadelphia 4 times per day from Monday through Friday.
    Yes, Southwest flies nonstop from Chicago (Midway) to Philadelphia 3 times per day on Saturdays and 5 times per day on Sundays.
    To find the lowest fares by day and time to fly Chicago (Midway) to Philadelphia with Southwest, check out our Low Fare Calendar.
    You can rent a car at Philadelphia International Airport book yours with your flight.
    Yes! Flights from Chicago (Midway) to Philadelphia—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.

    Explore Flights from Other Popular Origins

    Popular Flights from Chicago-Midway