Southwest® flights from Pittsburgh to Chicago-Midway from $122

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Low fares from Pittsburgh to Chicago-Midway

$

Pittsburgh (PIT)to

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

One-way

Basic

From
$122
Seen: 11 hrs ago

Pittsburgh (PIT)to

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

One-way

Basic

From
$122
Seen: 9 hrs ago

Pittsburgh (PIT)to

Chicago-Midway (MDW)
Depart: 12/11/2026

One-way

Basic

From
$122
Seen: 12 hrs ago

Pittsburgh (PIT)to

Chicago-Midway (MDW)
Depart: 11/12/2026

One-way

Basic

From
$122
Seen: 13 hrs ago

Pittsburgh (PIT)to

Chicago-Midway (MDW)
Depart: 11/17/2026

One-way

Basic

From
$122
Seen: 4 hrs ago

Pittsburgh (PIT)to

Chicago-Midway (MDW)
Depart: 11/22/2026

One-way

Basic

From
$122
Seen: 5 hrs ago

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Explore flights from Pittsburgh to Chicago-Midway

Oct 2026
From$267*
Seen: 5 hrs ago
One Way/Basic
Nov 2026
From$122*
Seen: 10 hrs ago
One Way/Basic
Dec 2026
From$122*
Seen: 4 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $122
cmp-daily-histogram-bars-legend-max-price-aria-label $309
Displaying fares for October-2026
  • PIT–MDW, 10/20/2026: From $278
    20

    Tue

    OCT

  • PIT–MDW, 10/21/2026: From $267
    21

    Wed

  • PIT–MDW, 10/22/2026: From $309
    22

    Thu

  • PIT–MDW, 10/23/2026: From $309
    23

    Fri

  • PIT–MDW, 10/24/2026: From $267
    24

    Sat

  • PIT–MDW, 10/25/2026: From $309
    25

    Sun

  • PIT–MDW, 10/26/2026: From $309
    26

    Mon

  • PIT–MDW, 10/27/2026: From $267
    27

    Tue

  • PIT–MDW, 10/28/2026: From $278
    28

    Wed

  • PIT–MDW, 10/29/2026: From $309
    29

    Thu

  • PIT–MDW: cmp-view-offers-disclaimer. Find Offers
    30

    Fri

  • PIT–MDW: cmp-view-offers-disclaimer. Find Offers
    31

    Sat

  • PIT–MDW: cmp-view-offers-disclaimer. Find Offers
    01

    Sun

    NOV

  • PIT–MDW: cmp-view-offers-disclaimer. Find Offers
    02

    Mon

  • PIT–MDW, 11/03/2026: From $267
    03

    Tue

  • PIT–MDW, 11/04/2026: From $267
    04

    Wed

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

    Thu

  • PIT–MDW, 11/06/2026: From $285
    06

    Fri

  • PIT–MDW, 11/07/2026: From $278
    07

    Sat

  • PIT–MDW, 11/08/2026: From $285
    08

    Sun

  • PIT–MDW, 11/09/2026: From $122
    09

    Mon

  • PIT–MDW, 11/10/2026: From $122
    10

    Tue

  • PIT–MDW, 11/11/2026: From $122
    11

    Wed

  • PIT–MDW, 11/12/2026: From $122
    12

    Thu

  • PIT–MDW, 11/13/2026: From $122
    13

    Fri

  • PIT–MDW: cmp-view-offers-disclaimer. Find Offers
    14

    Sat

  • PIT–MDW, 11/15/2026: From $122
    15

    Sun

  • PIT–MDW, 11/16/2026: From $122
    16

    Mon

  • PIT–MDW, 11/17/2026: From $122
    17

    Tue

  • PIT–MDW, 11/18/2026: From $122
    18

    Wed

  • PIT–MDW, 11/19/2026: From $122
    19

    Thu

    • Range$122-$309

    *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:
    Pittsburgh International Airport
    Arriving at:
    Chicago Midway International Airport
    Average flight time:
    1 hour 27 minutes
    Distance:
    402 miles

    Questions we hear the most

    The average flight time from Pittsburgh to Chicago (Midway) is 1 hour 27 minutes.
    There are 133 weekly flights from Pittsburgh to Chicago (Midway) on Southwest Airlines.
    Yes, Southwest flies nonstop from Pittsburgh to Chicago (Midway) 3 times per day from Monday through Friday.
    Yes, Southwest flies nonstop from Pittsburgh to Chicago (Midway) 2 times per day on Saturdays and 4 times per day on Sundays.
    To find the lowest fares by day and time to fly Pittsburgh 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 Pittsburgh 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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