Southwest® flights from Chicago-Midway to Pittsburgh from $152

Promo Code

Low fares from Chicago-Midway to Pittsburgh

$

Chicago-Midway (MDW)to

Pittsburgh (PIT)
Depart: 10/10/2026

One-way

Basic

From
$152
Seen: 14 hrs ago

Chicago-Midway (MDW)to

Pittsburgh (PIT)
Depart: 10/22/2026

One-way

Basic

From
$152
Seen: 15 hrs ago

Chicago-Midway (MDW)to

Pittsburgh (PIT)
Depart: 12/17/2026

One-way

Basic

From
$152
Seen: 8 hrs ago

Chicago-Midway (MDW)to

Pittsburgh (PIT)
Depart: 11/09/2026

One-way

Basic

From
$152
Seen: 1 hour ago

Chicago-Midway (MDW)to

Pittsburgh (PIT)
Depart: 12/12/2026

One-way

Basic

From
$152
Seen: 2 hrs ago

Chicago-Midway (MDW)to

Pittsburgh (PIT)
Depart: 10/20/2026

One-way

Basic

From
$152
Seen: 1 hour ago

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Explore flights from Chicago-Midway to Pittsburgh

Sep 2026
From$260*
Seen: 15 hrs ago
One Way/Basic
Oct 2026
From$152*
Seen: 22 hrs ago
One Way/Basic
Nov 2026
From$152*
Seen: 9 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $152
cmp-daily-histogram-bars-legend-max-price-aria-label $289
Displaying fares for September-2026
  • MDW–PIT, 09/11/2026: From $289
    11

    Fri

    SEP

  • MDW–PIT, 09/12/2026: From $260
    12

    Sat

  • MDW–PIT, 09/13/2026: From $289
    13

    Sun

  • MDW–PIT, 09/14/2026: From $289
    14

    Mon

  • MDW–PIT, 09/15/2026: From $270
    15

    Tue

  • MDW–PIT, 09/16/2026: From $260
    16

    Wed

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

    Thu

  • MDW–PIT, 09/18/2026: From $289
    18

    Fri

  • MDW–PIT, 09/19/2026: From $260
    19

    Sat

  • MDW–PIT, 09/20/2026: From $289
    20

    Sun

  • MDW–PIT, 09/21/2026: From $289
    21

    Mon

  • MDW–PIT, 09/22/2026: From $260
    22

    Tue

  • MDW–PIT, 09/23/2026: From $270
    23

    Wed

  • MDW–PIT: cmp-view-offers-disclaimer. Find Offers
    24

    Thu

  • MDW–PIT, 09/25/2026: From $265
    25

    Fri

  • MDW–PIT, 09/26/2026: From $260
    26

    Sat

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

    Sun

  • MDW–PIT, 09/28/2026: From $265
    28

    Mon

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

    Tue

  • MDW–PIT, 09/30/2026: From $260
    30

    Wed

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

    Thu

    OCT

  • MDW–PIT, 10/02/2026: From $161
    02

    Fri

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

    Sat

  • MDW–PIT, 10/04/2026: From $225
    04

    Sun

  • MDW–PIT: cmp-view-offers-disclaimer. Find Offers
    05

    Mon

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

    Tue

  • MDW–PIT, 10/07/2026: From $152
    07

    Wed

  • MDW–PIT, 10/08/2026: From $190
    08

    Thu

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

    Fri

  • MDW–PIT, 10/10/2026: From $152
    10

    Sat

    • Range$152-$289

    *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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