Southwest® flights from Phoenix to Chicago-Midway from $153

Promo Code

Low fares from Phoenix to Chicago-Midway

$

Phoenix (PHX)to

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

One-way

Basic

From
$153
Seen: 8 hrs ago

Phoenix (PHX)to

Chicago-Midway (MDW)
Depart: 01/12/2027

One-way

Basic

From
$153
Seen: 22 hrs ago

Phoenix (PHX)to

Chicago-Midway (MDW)
Depart: 02/03/2027

One-way

Basic

From
$153
Seen: 21 hrs ago

Phoenix (PHX)to

Chicago-Midway (MDW)
Depart: 01/05/2027

One-way

Basic

From
$153
Seen: 8 hrs ago

Phoenix (PHX)to

Chicago-Midway (MDW)
Depart: 02/06/2027

One-way

Basic

From
$158
Seen: 9 hrs ago

Phoenix (PHX)to

Chicago-Midway (MDW)
Depart: 12/01/2026

One-way

Basic

From
$158
Seen: 6 hrs ago

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Explore flights from Phoenix to Chicago-Midway

Nov 2026
From$288*
Seen: 5 hrs ago
One Way/Basic
Dec 2026
From$158*
Seen: 5 hrs ago
One Way/Basic
Jan 2027
From$153*
Seen: 8 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $158
cmp-daily-histogram-bars-legend-max-price-aria-label $468
Displaying fares for November-2026
  • PHX–MDW: cmp-view-offers-disclaimer. Find Offers
    11

    Wed

    NOV

  • PHX–MDW, 11/12/2026: From $316
    12

    Thu

  • PHX–MDW, 11/13/2026: From $316
    13

    Fri

  • PHX–MDW, 11/14/2026: From $301
    14

    Sat

  • PHX–MDW, 11/15/2026: From $316
    15

    Sun

  • PHX–MDW, 11/16/2026: From $326
    16

    Mon

  • PHX–MDW, 11/17/2026: From $288
    17

    Tue

  • PHX–MDW, 11/18/2026: From $288
    18

    Wed

  • PHX–MDW, 11/19/2026: From $316
    19

    Thu

  • PHX–MDW, 11/20/2026: From $316
    20

    Fri

  • PHX–MDW, 11/21/2026: From $301
    21

    Sat

  • PHX–MDW, 11/22/2026: From $316
    22

    Sun

  • PHX–MDW, 11/23/2026: From $316
    23

    Mon

  • PHX–MDW, 11/24/2026: From $288
    24

    Tue

  • PHX–MDW, 11/25/2026: From $288
    25

    Wed

  • PHX–MDW, 11/26/2026: From $316
    26

    Thu

  • PHX–MDW, 11/27/2026: From $316
    27

    Fri

  • PHX–MDW, 11/28/2026: From $385
    28

    Sat

  • PHX–MDW, 11/29/2026: From $468
    29

    Sun

  • PHX–MDW, 11/30/2026: From $316
    30

    Mon

  • PHX–MDW, 12/01/2026: From $158
    01

    Tue

    DEC

  • PHX–MDW, 12/02/2026: From $158
    02

    Wed

  • PHX–MDW, 12/03/2026: From $178
    03

    Thu

  • PHX–MDW, 12/04/2026: From $193
    04

    Fri

  • PHX–MDW, 12/05/2026: From $158
    05

    Sat

  • PHX–MDW, 12/06/2026: From $284
    06

    Sun

  • PHX–MDW, 12/07/2026: From $178
    07

    Mon

  • PHX–MDW, 12/08/2026: From $158
    08

    Tue

  • PHX–MDW, 12/09/2026: From $158
    09

    Wed

  • PHX–MDW, 12/10/2026: From $178
    10

    Thu

    • Range$158-$468

    *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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