Southwest® flights from Chicago-Midway to Pittsburgh from $155

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Low fares from Chicago-Midway to Pittsburgh

$

Chicago-Midway (MDW)to

Pittsburgh (PIT)
Depart: 12/12/2026

One-way

Basic

From
$155
Seen: 22 hrs ago

Chicago-Midway (MDW)to

Pittsburgh (PIT)
Depart: 01/12/2027

One-way

Basic

From
$155
Seen: 15 hrs ago

Chicago-Midway (MDW)to

Pittsburgh (PIT)
Depart: 12/22/2026

One-way

Basic

From
$155
Seen: 23 hrs ago

Chicago-Midway (MDW)to

Pittsburgh (PIT)
Depart: 12/08/2026

One-way

Basic

From
$155
Seen: 19 hrs ago

Chicago-Midway (MDW)to

Pittsburgh (PIT)
Depart: 01/23/2027

One-way

Basic

From
$155
Seen: 10 hrs ago

Chicago-Midway (MDW)to

Pittsburgh (PIT)
Depart: 12/30/2026

One-way

Basic

From
$155
Seen: 11 hrs ago

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Explore flights from Chicago-Midway to Pittsburgh

Nov 2026
From$260*
Seen: 16 hrs ago
One Way/Basic
Dec 2026
From$155*
Seen: 23 hrs ago
One Way/Basic
Jan 2027
From$155*
Seen: 22 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $155
cmp-daily-histogram-bars-legend-max-price-aria-label $265
Displaying fares for November-2026
  • MDW–PIT, 11/13/2026: From $260
    13

    Fri

    NOV

  • MDW–PIT, 11/14/2026: From $260
    14

    Sat

  • MDW–PIT, 11/15/2026: From $265
    15

    Sun

  • MDW–PIT, 11/16/2026: From $260
    16

    Mon

  • MDW–PIT, 11/17/2026: From $260
    17

    Tue

  • MDW–PIT, 11/18/2026: From $265
    18

    Wed

  • MDW–PIT: cmp-view-offers-disclaimer. Find Offers
    19

    Thu

  • MDW–PIT, 11/20/2026: From $265
    20

    Fri

  • MDW–PIT, 11/21/2026: From $260
    21

    Sat

  • MDW–PIT, 11/22/2026: From $260
    22

    Sun

  • MDW–PIT, 11/23/2026: From $260
    23

    Mon

  • MDW–PIT, 11/24/2026: From $260
    24

    Tue

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

    Wed

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

    Thu

  • MDW–PIT, 11/27/2026: From $260
    27

    Fri

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

    Sat

  • MDW–PIT, 11/29/2026: From $260
    29

    Sun

  • MDW–PIT, 11/30/2026: From $260
    30

    Mon

  • MDW–PIT, 12/01/2026: From $265
    01

    Tue

    DEC

  • MDW–PIT, 12/02/2026: From $155
    02

    Wed

  • MDW–PIT: cmp-view-offers-disclaimer. Find Offers
    03

    Thu

  • MDW–PIT, 12/04/2026: From $190
    04

    Fri

  • MDW–PIT, 12/05/2026: From $155
    05

    Sat

  • MDW–PIT, 12/06/2026: From $250
    06

    Sun

  • MDW–PIT, 12/07/2026: From $175
    07

    Mon

  • MDW–PIT, 12/08/2026: From $155
    08

    Tue

  • MDW–PIT: cmp-view-offers-disclaimer. Find Offers
    09

    Wed

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

    Thu

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

    Fri

  • MDW–PIT, 12/12/2026: From $155
    12

    Sat

    • Range$155-$265

    *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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