Southwest® flights from Phoenix to Chicago-Midway from $133

Promo Code

Low fares from Phoenix to Chicago-Midway

$

Phoenix (PHX)to

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

One-way

Basic

From
$133
Seen: 1 hour ago

Phoenix (PHX)to

Chicago-Midway (MDW)
Depart: 10/08/2026

One-way

Basic

From
$134
Seen: 20 hrs ago

Phoenix (PHX)to

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

One-way

Basic

From
$134
Seen: 20 hrs ago

Phoenix (PHX)to

Chicago-Midway (MDW)
Depart: 10/21/2026

One-way

Basic

From
$134
Seen: 21 hrs ago

Phoenix (PHX)to

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

One-way

Basic

From
$134
Seen: 22 hrs ago

Phoenix (PHX)to

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

One-way

Basic

From
$134
Seen: 11 hrs ago

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Explore flights from Phoenix to Chicago-Midway

Sep 2026
From$227*
Seen: 2 hrs ago
One Way/Basic
Oct 2026
From$133*
Seen: 1 hour ago
One Way/Basic
Nov 2026
From$134*
Seen: 19 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $134
cmp-daily-histogram-bars-legend-max-price-aria-label $290
Displaying fares for September-2026
  • PHX–MDW, 09/11/2026: From $280
    11

    Fri

    SEP

  • PHX–MDW, 09/12/2026: From $231
    12

    Sat

  • PHX–MDW, 09/13/2026: From $280
    13

    Sun

  • PHX–MDW, 09/14/2026: From $290
    14

    Mon

  • PHX–MDW, 09/15/2026: From $231
    15

    Tue

  • PHX–MDW, 09/16/2026: From $231
    16

    Wed

  • PHX–MDW, 09/17/2026: From $285
    17

    Thu

  • PHX–MDW, 09/18/2026: From $285
    18

    Fri

  • PHX–MDW, 09/19/2026: From $241
    19

    Sat

  • PHX–MDW, 09/20/2026: From $227
    20

    Sun

  • PHX–MDW, 09/21/2026: From $280
    21

    Mon

  • PHX–MDW, 09/22/2026: From $231
    22

    Tue

  • PHX–MDW, 09/23/2026: From $241
    23

    Wed

  • PHX–MDW, 09/24/2026: From $290
    24

    Thu

  • PHX–MDW, 09/25/2026: From $290
    25

    Fri

  • PHX–MDW, 09/26/2026: From $231
    26

    Sat

  • PHX–MDW, 09/27/2026: From $290
    27

    Sun

  • PHX–MDW, 09/28/2026: From $280
    28

    Mon

  • PHX–MDW, 09/29/2026: From $231
    29

    Tue

  • PHX–MDW, 09/30/2026: From $231
    30

    Wed

  • PHX–MDW, 10/01/2026: From $134
    01

    Thu

    OCT

  • PHX–MDW, 10/02/2026: From $162
    02

    Fri

  • PHX–MDW, 10/03/2026: From $134
    03

    Sat

  • PHX–MDW, 10/04/2026: From $259
    04

    Sun

  • PHX–MDW, 10/05/2026: From $162
    05

    Mon

  • PHX–MDW, 10/06/2026: From $134
    06

    Tue

  • PHX–MDW, 10/07/2026: From $134
    07

    Wed

  • PHX–MDW, 10/08/2026: From $134
    08

    Thu

  • PHX–MDW, 10/09/2026: From $150
    09

    Fri

  • PHX–MDW, 10/10/2026: From $162
    10

    Sat

    • Range$134-$290

    *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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