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

Promo Code

Low fares from Pittsburgh to Chicago-Midway

$

Pittsburgh (PIT)to

Chicago-Midway (MDW)
Depart: 01/05/2027

One-way

Basic

From
$139
Seen: 15 hrs ago

Pittsburgh (PIT)to

Chicago-Midway (MDW)
Depart: 12/22/2026

One-way

Basic

From
$139
Seen: 18 hrs ago

Pittsburgh (PIT)to

Chicago-Midway (MDW)
Depart: 11/16/2026

One-way

Basic

From
$139
Seen: 20 hrs ago

Pittsburgh (PIT)to

Chicago-Midway (MDW)
Depart: 11/12/2026

One-way

Basic

From
$139
Seen: 20 hrs ago

Pittsburgh (PIT)to

Chicago-Midway (MDW)
Depart: 11/09/2026

One-way

Basic

From
$139
Seen: 18 hrs ago

Pittsburgh (PIT)to

Chicago-Midway (MDW)
Depart: 01/07/2027

One-way

Basic

From
$139
Seen: 20 hrs ago

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Explore flights from Pittsburgh to Chicago-Midway

Try alternate month or interact with individual days below in order to find offers.
Sep 2026
No result for this month.
Oct 2026
From$139*
Seen: 7 hrs ago
One Way/Basic
Nov 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 $331
Displaying fares for September-2026
  • PIT–MDW: cmp-view-offers-disclaimer. Find Offers
    30

    Wed

    SEP

  • PIT–MDW, 10/01/2026: From $309
    01

    Thu

  • PIT–MDW, 10/02/2026: From $299
    02

    Fri

  • PIT–MDW, 10/03/2026: From $270
    03

    Sat

  • PIT–MDW: cmp-view-offers-disclaimer. Find Offers
    04

    Sun

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

    Mon

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

    Tue

  • PIT–MDW, 10/07/2026: From $270
    07

    Wed

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

    Thu

  • PIT–MDW, 10/09/2026: From $299
    09

    Fri

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

    Sat

  • PIT–MDW, 10/11/2026: From $331
    11

    Sun

  • PIT–MDW: cmp-view-offers-disclaimer. Find Offers
    12

    Mon

  • PIT–MDW, 10/13/2026: From $280
    13

    Tue

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

    Wed

  • PIT–MDW, 10/15/2026: From $275
    15

    Thu

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

    Fri

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

    Sat

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

    Sun

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

    Mon

  • PIT–MDW, 10/20/2026: From $139
    20

    Tue

  • PIT–MDW, 10/21/2026: From $139
    21

    Wed

  • PIT–MDW: cmp-view-offers-disclaimer. Find Offers
    22

    Thu

  • PIT–MDW: cmp-view-offers-disclaimer. Find Offers
    23

    Fri

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

    Sat

  • PIT–MDW, 10/25/2026: From $235
    25

    Sun

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

    Mon

  • PIT–MDW, 10/27/2026: From $139
    27

    Tue

  • PIT–MDW, 10/28/2026: From $139
    28

    Wed

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

    Thu

    • Range$139-$331

    *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:
    Pittsburgh International Airport
    Arriving at:
    Chicago Midway International Airport
    Average flight time:
    1 hour 27 minutes
    Distance:
    402 miles

    Route Information

    133† Weekly flights
    • 3‡ 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 Pittsburgh to Chicago (Midway) is 1 hour 27 minutes.
    There are 133 weekly flights from Pittsburgh to Chicago (Midway) on Southwest Airlines.
    Yes, Southwest flies nonstop from Pittsburgh to Chicago (Midway) 3 times per day from Monday through Friday.
    Yes, Southwest flies nonstop from Pittsburgh to Chicago (Midway) 2 times per day on Saturdays and 4 times per day on Sundays.
    To find the lowest fares by day and time to fly Pittsburgh to Chicago (Midway) with Southwest, check out our Low Fare Calendar.
    You can rent a car at Chicago Midway International Airport book yours with your flight.
    Yes! Flights from Pittsburgh to Chicago (Midway)—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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