Southwest® flights from Phoenix to Chicago-Midway from $110

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Low fares from Phoenix to Chicago-Midway

$

Phoenix (PHX)to

Chicago-Midway (MDW)
Depart: 12/10/2026

One-way

Basic

From
$110
Seen: 20 hrs ago

Phoenix (PHX)to

Chicago-Midway (MDW)
Depart: 11/21/2026

One-way

Basic

From
$110
Seen: 19 hrs ago

Phoenix (PHX)to

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

One-way

Basic

From
$110
Seen: 10 hrs ago

Phoenix (PHX)to

Chicago-Midway (MDW)
Depart: 01/07/2027

One-way

Basic

From
$110
Seen: 14 hrs ago

Phoenix (PHX)to

Chicago-Midway (MDW)
Depart: 01/23/2027

One-way

Basic

From
$110
Seen: 11 hrs ago

Phoenix (PHX)to

Chicago-Midway (MDW)
Depart: 12/09/2026

One-way

Basic

From
$110
Seen: 17 hrs ago

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Explore flights from Phoenix to Chicago-Midway

Oct 2026
From$251*
Seen: 7 hrs ago
One Way/Basic
Nov 2026
From$110*
Seen: 16 hrs ago
One Way/Basic
Dec 2026
From$110*
Seen: 19 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $110
cmp-daily-histogram-bars-legend-max-price-aria-label $337
Displaying fares for October-2026
  • PHX–MDW, 10/21/2026: From $251
    21

    Wed

    OCT

  • PHX–MDW, 10/22/2026: From $337
    22

    Thu

  • PHX–MDW, 10/23/2026: From $337
    23

    Fri

  • PHX–MDW, 10/24/2026: From $251
    24

    Sat

  • PHX–MDW, 10/25/2026: From $311
    25

    Sun

  • PHX–MDW, 10/26/2026: From $311
    26

    Mon

  • PHX–MDW, 10/27/2026: From $251
    27

    Tue

  • PHX–MDW, 10/28/2026: From $251
    28

    Wed

  • PHX–MDW, 10/29/2026: From $337
    29

    Thu

  • PHX–MDW, 10/30/2026: From $337
    30

    Fri

  • PHX–MDW, 10/31/2026: From $251
    31

    Sat

  • PHX–MDW, 11/01/2026: From $337
    01

    Sun

    NOV

  • PHX–MDW, 11/02/2026: From $337
    02

    Mon

  • PHX–MDW, 11/03/2026: From $251
    03

    Tue

  • PHX–MDW, 11/04/2026: From $251
    04

    Wed

  • PHX–MDW, 11/05/2026: From $311
    05

    Thu

  • PHX–MDW, 11/06/2026: From $324
    06

    Fri

  • PHX–MDW, 11/07/2026: From $251
    07

    Sat

  • PHX–MDW, 11/08/2026: From $324
    08

    Sun

  • PHX–MDW, 11/09/2026: From $115
    09

    Mon

  • PHX–MDW, 11/10/2026: From $110
    10

    Tue

  • PHX–MDW, 11/11/2026: From $110
    11

    Wed

  • PHX–MDW, 11/12/2026: From $110
    12

    Thu

  • PHX–MDW, 11/13/2026: From $131
    13

    Fri

  • PHX–MDW, 11/14/2026: From $110
    14

    Sat

  • PHX–MDW, 11/15/2026: From $131
    15

    Sun

  • PHX–MDW, 11/16/2026: From $279
    16

    Mon

  • PHX–MDW, 11/17/2026: From $110
    17

    Tue

  • PHX–MDW, 11/18/2026: From $110
    18

    Wed

  • PHX–MDW, 11/19/2026: From $194
    19

    Thu

  • PHX–MDW, 11/20/2026: From $157
    20

    Fri

    • Range$110-$337

    *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

    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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