Southwest® flights from Chicago-Midway to Pittsburgh from $139

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Low fares from Chicago-Midway to Pittsburgh

$

Chicago-Midway (MDW)to

Pittsburgh (PIT)
Depart: 10/22/2026

One-way

Basic

From
$139
Seen: 23 hrs ago

Chicago-Midway (MDW)to

Pittsburgh (PIT)
Depart: 12/07/2026

One-way

Basic

From
$139
Seen: 11 hrs ago

Chicago-Midway (MDW)to

Pittsburgh (PIT)
Depart: 12/17/2026

One-way

Basic

From
$139
Seen: 14 hrs ago

Chicago-Midway (MDW)to

Pittsburgh (PIT)
Depart: 12/16/2026

One-way

Basic

From
$139
Seen: 13 hrs ago

Chicago-Midway (MDW)to

Pittsburgh (PIT)
Depart: 11/21/2026

One-way

Basic

From
$139
Seen: 18 hrs ago

Chicago-Midway (MDW)to

Pittsburgh (PIT)
Depart: 10/26/2026

One-way

Basic

From
$139
Seen: 21 hrs ago

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Explore flights from Chicago-Midway to Pittsburgh

Oct 2026
From$139*
Seen: 21 hrs ago
One Way/Basic
Nov 2026
From$139*
Seen: 21 hrs ago
One Way/Basic
Dec 2026
From$139*
Seen: 23 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $139
cmp-daily-histogram-bars-legend-max-price-aria-label $390
Displaying fares for October-2026
  • MDW–PIT, 10/03/2026: From $270
    03

    Sat

    OCT

  • MDW–PIT, 10/04/2026: From $299
    04

    Sun

  • MDW–PIT, 10/05/2026: From $299
    05

    Mon

  • MDW–PIT, 10/06/2026: From $270
    06

    Tue

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

    Wed

  • MDW–PIT, 10/08/2026: From $299
    08

    Thu

  • MDW–PIT, 10/09/2026: From $390
    09

    Fri

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

    Sat

  • MDW–PIT, 10/11/2026: From $299
    11

    Sun

  • MDW–PIT, 10/12/2026: From $299
    12

    Mon

  • MDW–PIT, 10/13/2026: From $270
    13

    Tue

  • MDW–PIT, 10/14/2026: From $270
    14

    Wed

  • MDW–PIT, 10/15/2026: From $299
    15

    Thu

  • MDW–PIT, 10/16/2026: From $275
    16

    Fri

  • MDW–PIT, 10/17/2026: From $270
    17

    Sat

  • MDW–PIT, 10/18/2026: From $275
    18

    Sun

  • MDW–PIT, 10/19/2026: From $275
    19

    Mon

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

    Tue

  • MDW–PIT: cmp-view-offers-disclaimer. Find Offers
    21

    Wed

  • MDW–PIT, 10/22/2026: From $139
    22

    Thu

  • MDW–PIT, 10/23/2026: From $179
    23

    Fri

  • MDW–PIT, 10/24/2026: From $139
    24

    Sat

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

    Sun

  • MDW–PIT, 10/26/2026: From $139
    26

    Mon

  • MDW–PIT, 10/27/2026: From $179
    27

    Tue

  • MDW–PIT, 10/28/2026: From $179
    28

    Wed

  • MDW–PIT, 10/29/2026: From $179
    29

    Thu

  • MDW–PIT, 10/30/2026: From $179
    30

    Fri

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

    Sat

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

    Sun

    NOV

  • MDW–PIT, 11/02/2026: From $139
    02

    Mon

    • Range$139-$390

    *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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