Southwest® flights from Phoenix to Chicago (Midway) from $127

Promo Code

Low fares from Phoenix to Chicago (Midway)

$

Phoenix (PHX)to

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

One-way

Basic

From
$127
Seen: 1 hour ago

Phoenix (PHX)to

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

One-way

Basic

From
$127
Seen: 1 hour ago

Phoenix (PHX)to

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

One-way

Basic

From
$127
Seen: 47 minutes ago

Phoenix (PHX)to

Chicago (Midway) (MDW)
Depart: 11/03/2026

One-way

Basic

From
$140
Seen: 22 hrs ago

Phoenix (PHX)to

Chicago (Midway) (MDW)
Depart: 10/15/2026

One-way

Basic

From
$140
Seen: 20 hrs ago

Phoenix (PHX)to

Chicago (Midway) (MDW)
Depart: 10/06/2026

One-way

Basic

From
$140
Seen: 14 hrs ago

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Explore flights from Phoenix to Chicago (Midway)

Aug 2026
From$140*
Seen: 2 hrs ago
One Way/Basic
Sep 2026
From$127*
Seen: 1 hour ago
One Way/Basic
Oct 2026
From$140*
Seen: 23 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $140
cmp-daily-histogram-bars-legend-max-price-aria-label $276
Displaying fares for August-2026
  • PHX–MDW, 08/01/2026: From $260
    01

    Sat

    AUG

  • PHX–MDW, 08/02/2026: From $271
    02

    Sun

  • PHX–MDW, 08/03/2026: From $271
    03

    Mon

  • PHX–MDW, 08/04/2026: From $221
    04

    Tue

  • PHX–MDW, 08/05/2026: From $226
    05

    Wed

  • PHX–MDW, 08/06/2026: From $276
    06

    Thu

  • PHX–MDW, 08/07/2026: From $271
    07

    Fri

  • PHX–MDW, 08/08/2026: From $221
    08

    Sat

  • PHX–MDW, 08/09/2026: From $271
    09

    Sun

  • PHX–MDW, 08/10/2026: From $271
    10

    Mon

  • PHX–MDW, 08/11/2026: From $221
    11

    Tue

  • PHX–MDW, 08/12/2026: From $221
    12

    Wed

  • PHX–MDW, 08/13/2026: From $271
    13

    Thu

  • PHX–MDW, 08/14/2026: From $271
    14

    Fri

  • PHX–MDW, 08/15/2026: From $221
    15

    Sat

  • PHX–MDW, 08/16/2026: From $271
    16

    Sun

  • PHX–MDW, 08/17/2026: From $271
    17

    Mon

  • PHX–MDW, 08/18/2026: From $221
    18

    Tue

  • PHX–MDW, 08/19/2026: From $221
    19

    Wed

  • PHX–MDW, 08/20/2026: From $271
    20

    Thu

  • PHX–MDW, 08/21/2026: From $152
    21

    Fri

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

    Sat

  • PHX–MDW, 08/23/2026: From $249
    23

    Sun

  • PHX–MDW: cmp-view-offers-disclaimer. Find Offers
    24

    Mon

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

    Tue

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

    Wed

  • PHX–MDW, 08/27/2026: From $145
    27

    Thu

  • PHX–MDW, 08/28/2026: From $152
    28

    Fri

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

    Sat

  • PHX–MDW, 08/30/2026: From $164
    30

    Sun

  • PHX–MDW, 08/31/2026: From $140
    31

    Mon

    • Range$140-$276

    *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:
    Sky Harbor International Airport
    Arriving at:
    Chicago Midway International Airport
    Average flight time:
    3 hours 17 minutes
    Distance:
    1444 miles

    Route Information

    156† Weekly flights
    • 8‡ Nonstop flights per day Monday through Friday
    • 6‡ Nonstop flights on Saturday
    • 9‡ 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 Phoenix to Chicago (Midway) is 3 hours 17 minutes.
    There are 156 weekly flights from Phoenix to Chicago (Midway) on Southwest Airlines.
    Yes, Southwest flies nonstop from Phoenix to Chicago (Midway) 8 times per day from Monday through Friday.
    Yes, Southwest flies nonstop from Phoenix to Chicago (Midway) 6 times per day on Saturdays and 9 times per day on Sundays.
    To find the lowest fares by day and time to fly Phoenix 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 Phoenix 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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