Southwest® flights from Chicago-Midway to Pittsburgh from $121

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Low fares from Chicago-Midway to Pittsburgh

$

Chicago-Midway (MDW)to

Pittsburgh (PIT)
Depart: 01/07/2027

One-way

Basic

From
$121
Seen: 16 minutes ago

Chicago-Midway (MDW)to

Pittsburgh (PIT)
Depart: 12/24/2026

One-way

Basic

From
$121
Seen: 4 hrs ago

Chicago-Midway (MDW)to

Pittsburgh (PIT)
Depart: 12/22/2026

One-way

Basic

From
$121
Seen: 3 hrs ago

Chicago-Midway (MDW)to

Pittsburgh (PIT)
Depart: 12/04/2026

One-way

Basic

From
$121
Seen: 1 hour ago

Chicago-Midway (MDW)to

Pittsburgh (PIT)
Depart: 11/14/2026

One-way

Basic

From
$121
Seen: 4 hrs ago

Chicago-Midway (MDW)to

Pittsburgh (PIT)
Depart: 11/27/2026

One-way

Basic

From
$121
Seen: 4 hrs ago

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Explore flights from Chicago-Midway to Pittsburgh

Oct 2026
From$265*
Seen: 3 hrs ago
One Way/Basic
Nov 2026
From$121*
Seen: 4 hrs ago
One Way/Basic
Dec 2026
From$121*
Seen: 4 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $121
cmp-daily-histogram-bars-legend-max-price-aria-label $309
Displaying fares for October-2026
  • MDW–PIT, 10/24/2026: From $265
    24

    Sat

    OCT

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

    Sun

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

    Mon

  • MDW–PIT, 10/27/2026: From $266
    27

    Tue

  • MDW–PIT: cmp-view-offers-disclaimer. Find Offers
    28

    Wed

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

    Thu

  • MDW–PIT, 10/30/2026: From $309
    30

    Fri

  • MDW–PIT, 10/31/2026: From $266
    31

    Sat

  • MDW–PIT, 11/01/2026: From $309
    01

    Sun

    NOV

  • MDW–PIT, 11/02/2026: From $309
    02

    Mon

  • MDW–PIT, 11/03/2026: From $266
    03

    Tue

  • MDW–PIT, 11/04/2026: From $266
    04

    Wed

  • MDW–PIT, 11/05/2026: From $309
    05

    Thu

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

    Fri

  • MDW–PIT, 11/07/2026: From $266
    07

    Sat

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

    Sun

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

    Mon

  • MDW–PIT: cmp-view-offers-disclaimer. Find Offers
    10

    Tue

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

    Wed

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

    Thu

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

    Fri

  • MDW–PIT, 11/14/2026: From $121
    14

    Sat

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

    Sun

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

    Mon

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

    Tue

  • MDW–PIT: cmp-view-offers-disclaimer. Find Offers
    18

    Wed

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

    Thu

  • MDW–PIT, 11/20/2026: From $122
    20

    Fri

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

    Sat

  • MDW–PIT, 11/22/2026: From $122
    22

    Sun

  • MDW–PIT, 11/23/2026: From $122
    23

    Mon

    • Range$121-$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:
    Chicago Midway International Airport
    Arriving at:
    Pittsburgh International Airport
    Average flight time:
    1 hour 20 minutes
    Distance:
    402 miles

    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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