Southwest® flights from Chicago (Midway) to Pittsburgh from $69

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Low fares from Chicago (Midway) to Pittsburgh

$

Chicago (Midway) (MDW)to

Pittsburgh (PIT)
Depart: 09/23/2026

One-way

Basic

From
$69
Seen: 19 hrs ago

Chicago (Midway) (MDW)to

Pittsburgh (PIT)
Depart: 10/15/2026

One-way

Basic

From
$69
Seen: 18 hrs ago

Chicago (Midway) (MDW)to

Pittsburgh (PIT)
Depart: 09/28/2026

One-way

Basic

From
$69
Seen: 21 hrs ago

Chicago (Midway) (MDW)to

Pittsburgh (PIT)
Depart: 10/20/2026

One-way

Basic

From
$69
Seen: 15 hrs ago

Chicago (Midway) (MDW)to

Pittsburgh (PIT)
Depart: 11/02/2026

One-way

Basic

From
$69
Seen: 15 hrs ago

Chicago (Midway) (MDW)to

Pittsburgh (PIT)
Depart: 09/22/2026

One-way

Basic

From
$69
Seen: 9 hrs ago

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Explore flights from Chicago (Midway) to Pittsburgh

Aug 2026
From$250*
Seen: 4 hrs ago
One Way/Basic
Sep 2026
From$69*
Seen: 17 hrs ago
One Way/Basic
Oct 2026
From$69*
Seen: 16 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $69
cmp-daily-histogram-bars-legend-max-price-aria-label $279
Displaying fares for August-2026
  • MDW–PIT, 08/22/2026: From $250
    22

    Sat

    AUG

  • MDW–PIT, 08/23/2026: From $279
    23

    Sun

  • MDW–PIT, 08/24/2026: From $279
    24

    Mon

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

    Tue

  • MDW–PIT: cmp-view-offers-disclaimer. Find Offers
    26

    Wed

  • MDW–PIT, 08/27/2026: From $279
    27

    Thu

  • MDW–PIT, 08/28/2026: From $279
    28

    Fri

  • MDW–PIT: cmp-view-offers-disclaimer. Find Offers
    29

    Sat

  • MDW–PIT, 08/30/2026: From $279
    30

    Sun

  • MDW–PIT, 08/31/2026: From $279
    31

    Mon

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

    Tue

    SEP

  • MDW–PIT, 09/02/2026: From $250
    02

    Wed

  • MDW–PIT, 09/03/2026: From $255
    03

    Thu

  • MDW–PIT, 09/04/2026: From $255
    04

    Fri

  • MDW–PIT, 09/05/2026: From $200
    05

    Sat

  • MDW–PIT: cmp-view-offers-disclaimer. Find Offers
    06

    Sun

  • MDW–PIT, 09/07/2026: From $255
    07

    Mon

  • MDW–PIT: cmp-view-offers-disclaimer. Find Offers
    08

    Tue

  • MDW–PIT, 09/09/2026: From $200
    09

    Wed

  • MDW–PIT, 09/10/2026: From $69
    10

    Thu

  • MDW–PIT, 09/11/2026: From $96
    11

    Fri

  • MDW–PIT, 09/12/2026: From $96
    12

    Sat

  • MDW–PIT: cmp-view-offers-disclaimer. Find Offers
    13

    Sun

  • MDW–PIT, 09/14/2026: From $69
    14

    Mon

  • MDW–PIT, 09/15/2026: From $69
    15

    Tue

  • MDW–PIT, 09/16/2026: From $69
    16

    Wed

  • MDW–PIT, 09/17/2026: From $69
    17

    Thu

  • MDW–PIT, 09/18/2026: From $96
    18

    Fri

  • MDW–PIT, 09/19/2026: From $69
    19

    Sat

  • MDW–PIT, 09/20/2026: From $188
    20

    Sun

  • MDW–PIT, 09/21/2026: From $69
    21

    Mon

    • Range$69-$279

    *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:
    Chicago Midway International Airport
    Arriving at:
    Pittsburgh International Airport
    Average flight time:
    1 hour 20 minutes
    Distance:
    402 miles

    Route Information

    139† Weekly flights
    • 4‡ Nonstop flights per day Monday through Friday
    • 2‡ Nonstop flights on Saturday
    • 4‡ Nonstop flights on Sunday

    † Weekly flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025. Note: route may not operate every day of the week.

    ‡ Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025.

    Questions we hear the most

    The average flight time from Chicago (Midway) to Pittsburgh is 1 hour 20 minutes.
    There are 139 weekly flights from Chicago (Midway) to Pittsburgh on Southwest Airlines.
    Yes, Southwest flies nonstop from Chicago (Midway) to Pittsburgh 4 times per day from Monday through Friday.
    Yes, Southwest flies nonstop from Chicago (Midway) to Pittsburgh 2 times per day on Saturdays and 4 times per day on Sundays.
    To find the lowest fares by day and time to fly Chicago (Midway) to Pittsburgh with Southwest, check out our Low Fare Calendar.
    You can rent a car at Pittsburgh International Airport book yours with your flight.
    Yes! Flights from Chicago (Midway) to Pittsburgh—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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