Southwest® flights from Pittsburgh to Chicago-Midway from $149

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Low fares from Pittsburgh to Chicago-Midway

$

Pittsburgh (PIT)to

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

One-way

Basic

From
$149
Seen: 12 hrs ago

Pittsburgh (PIT)to

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

One-way

Basic

From
$149
Seen: 1 hour ago

Pittsburgh (PIT)to

Chicago-Midway (MDW)
Depart: 12/25/2026

One-way

Basic

From
$149
Seen: 7 hrs ago

Pittsburgh (PIT)to

Chicago-Midway (MDW)
Depart: 01/04/2027

One-way

Basic

From
$149
Seen: 6 hrs ago

Pittsburgh (PIT)to

Chicago-Midway (MDW)
Depart: 11/23/2026

One-way

Basic

From
$149
Seen: 11 hrs ago

Pittsburgh (PIT)to

Chicago-Midway (MDW)
Depart: 12/31/2026

One-way

Basic

From
$149
Seen: 8 hrs ago

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Explore flights from Pittsburgh to Chicago-Midway

Oct 2026
From$279*
Seen: 23 hrs ago
One Way/Basic
Nov 2026
From$149*
Seen: 11 hrs ago
One Way/Basic
Dec 2026
From$149*
Seen: 8 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $159
cmp-daily-histogram-bars-legend-max-price-aria-label $309
Displaying fares for October-2026
  • PIT–MDW: cmp-view-offers-disclaimer. Find Offers
    17

    Sat

    OCT

  • PIT–MDW, 10/18/2026: From $309
    18

    Sun

  • PIT–MDW, 10/19/2026: From $309
    19

    Mon

  • PIT–MDW, 10/20/2026: From $279
    20

    Tue

  • PIT–MDW, 10/21/2026: From $279
    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 $279
    24

    Sat

  • PIT–MDW: cmp-view-offers-disclaimer. Find Offers
    25

    Sun

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

    Mon

  • PIT–MDW: cmp-view-offers-disclaimer. Find Offers
    27

    Tue

  • PIT–MDW, 10/28/2026: From $279
    28

    Wed

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

    Thu

  • PIT–MDW, 10/30/2026: From $300
    30

    Fri

  • PIT–MDW, 10/31/2026: From $279
    31

    Sat

  • PIT–MDW, 11/01/2026: From $285
    01

    Sun

    NOV

  • PIT–MDW, 11/02/2026: From $300
    02

    Mon

  • PIT–MDW, 11/03/2026: From $279
    03

    Tue

  • PIT–MDW, 11/04/2026: From $279
    04

    Wed

  • PIT–MDW, 11/05/2026: From $285
    05

    Thu

  • PIT–MDW, 11/06/2026: From $159
    06

    Fri

  • PIT–MDW: cmp-view-offers-disclaimer. Find Offers
    07

    Sat

  • PIT–MDW, 11/08/2026: From $189
    08

    Sun

  • PIT–MDW, 11/09/2026: From $159
    09

    Mon

  • PIT–MDW, 11/10/2026: From $159
    10

    Tue

  • PIT–MDW: cmp-view-offers-disclaimer. Find Offers
    11

    Wed

  • PIT–MDW, 11/12/2026: From $159
    12

    Thu

  • PIT–MDW, 11/13/2026: From $159
    13

    Fri

  • PIT–MDW, 11/14/2026: From $159
    14

    Sat

  • PIT–MDW: cmp-view-offers-disclaimer. Find Offers
    15

    Sun

  • PIT–MDW, 11/16/2026: From $159
    16

    Mon

    • Range$159-$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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