Southwest® flights from Pittsburgh to Chicago-Midway from $150

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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
$150
Seen: 22 hrs ago

Pittsburgh (PIT)to

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

One-way

Basic

From
$150
Seen: 23 hrs ago

Pittsburgh (PIT)to

Chicago-Midway (MDW)
Depart: 01/13/2027

One-way

Basic

From
$150
Seen: 11 hrs ago

Pittsburgh (PIT)to

Chicago-Midway (MDW)
Depart: 12/22/2026

One-way

Basic

From
$150
Seen: 3 hrs ago

Pittsburgh (PIT)to

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

One-way

Basic

From
$150
Seen: 11 hrs ago

Pittsburgh (PIT)to

Chicago-Midway (MDW)
Depart: 02/10/2027

One-way

Basic

From
$150
Seen: 15 hrs ago

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Explore flights from Pittsburgh to Chicago-Midway

Nov 2026
From$270*
Seen: 9 hrs ago
One Way/Basic
Dec 2026
From$150*
Seen: 20 hrs ago
One Way/Basic
Jan 2027
From$150*
Seen: 19 minutes ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $150
cmp-daily-histogram-bars-legend-max-price-aria-label $370
Displaying fares for November-2026
  • PIT–MDW, 11/07/2026: From $270
    07

    Sat

    NOV

  • PIT–MDW, 11/08/2026: From $270
    08

    Sun

  • PIT–MDW, 11/09/2026: From $270
    09

    Mon

  • PIT–MDW, 11/10/2026: From $270
    10

    Tue

  • PIT–MDW, 11/11/2026: From $270
    11

    Wed

  • PIT–MDW, 11/12/2026: From $270
    12

    Thu

  • PIT–MDW, 11/13/2026: From $270
    13

    Fri

  • PIT–MDW, 11/14/2026: From $270
    14

    Sat

  • PIT–MDW, 11/15/2026: From $270
    15

    Sun

  • PIT–MDW, 11/16/2026: From $270
    16

    Mon

  • PIT–MDW: cmp-view-offers-disclaimer. Find Offers
    17

    Tue

  • PIT–MDW, 11/18/2026: From $270
    18

    Wed

  • PIT–MDW, 11/19/2026: From $270
    19

    Thu

  • PIT–MDW: cmp-view-offers-disclaimer. Find Offers
    20

    Fri

  • PIT–MDW, 11/21/2026: From $270
    21

    Sat

  • PIT–MDW, 11/22/2026: From $270
    22

    Sun

  • PIT–MDW: cmp-view-offers-disclaimer. Find Offers
    23

    Mon

  • PIT–MDW, 11/24/2026: From $270
    24

    Tue

  • PIT–MDW, 11/25/2026: From $270
    25

    Wed

  • PIT–MDW, 11/26/2026: From $270
    26

    Thu

  • PIT–MDW, 11/27/2026: From $270
    27

    Fri

  • PIT–MDW, 11/28/2026: From $370
    28

    Sat

  • PIT–MDW, 11/29/2026: From $270
    29

    Sun

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

    Mon

  • PIT–MDW, 12/01/2026: From $150
    01

    Tue

    DEC

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

    Wed

  • PIT–MDW, 12/03/2026: From $165
    03

    Thu

  • PIT–MDW, 12/04/2026: From $175
    04

    Fri

  • PIT–MDW, 12/05/2026: From $150
    05

    Sat

  • PIT–MDW, 12/06/2026: From $223
    06

    Sun

    • Range$150-$370

    *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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