Southwest® flights from Pittsburgh to Chicago (Midway) from $58

Promo Code

Low fares from Pittsburgh to Chicago (Midway)

$

Pittsburgh (PIT)to

Chicago (Midway) (MDW)
Depart: 10/30/2026

One-way

Basic

From
$58
Seen: 16 hrs ago

Pittsburgh (PIT)to

Chicago (Midway) (MDW)
Depart: 09/06/2026

One-way

Basic

From
$69
Seen: 12 hrs ago

Pittsburgh (PIT)to

Chicago (Midway) (MDW)
Depart: 10/30/2026

One-way

Choice

From
$90
Seen: 16 hrs ago

Pittsburgh (PIT)to

Chicago (Midway) (MDW)
Depart: 09/06/2026

One-way

Choice

From
$104
Seen: 12 hrs ago

Pittsburgh (PIT)to

Chicago (Midway) (MDW)
Depart: 09/08/2026

One-way

Basic

From
$112
Seen: 20 hrs ago

Pittsburgh (PIT)to

Chicago (Midway) (MDW)
Depart: 11/02/2026

One-way

Basic

From
$112
Seen: 21 hrs ago

Looking for more low-fare flights?

Check out the Low Fare Calendar to find a fare that works for you. Just choose the month you want to depart and return, and we’ll show you the best fares available.

Find low fares

Explore flights from Pittsburgh to Chicago (Midway)

Aug 2026
From$250*
Seen: 18 hrs ago
One Way/Basic
Sep 2026
From$69*
Seen: 12 hrs ago
One Way/Basic
Oct 2026
From$58*
Seen: 16 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $69
cmp-daily-histogram-bars-legend-max-price-aria-label $279
Displaying fares for August-2026
  • PIT–MDW, 08/13/2026: From $279
    13

    Thu

    AUG

  • PIT–MDW, 08/14/2026: From $279
    14

    Fri

  • PIT–MDW: cmp-view-offers-disclaimer. Find Offers
    15

    Sat

  • PIT–MDW, 08/16/2026: From $279
    16

    Sun

  • PIT–MDW, 08/17/2026: From $279
    17

    Mon

  • PIT–MDW, 08/18/2026: From $250
    18

    Tue

  • PIT–MDW, 08/19/2026: From $250
    19

    Wed

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

    Thu

  • PIT–MDW, 08/21/2026: From $279
    21

    Fri

  • PIT–MDW, 08/22/2026: From $250
    22

    Sat

  • PIT–MDW, 08/23/2026: From $279
    23

    Sun

  • PIT–MDW, 08/24/2026: From $279
    24

    Mon

  • PIT–MDW, 08/25/2026: From $250
    25

    Tue

  • PIT–MDW, 08/26/2026: From $250
    26

    Wed

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

    Thu

  • PIT–MDW, 08/28/2026: From $255
    28

    Fri

  • PIT–MDW, 08/29/2026: From $250
    29

    Sat

  • PIT–MDW, 08/30/2026: From $255
    30

    Sun

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

    Mon

  • PIT–MDW, 09/01/2026: From $112
    01

    Tue

    SEP

  • PIT–MDW, 09/02/2026: From $112
    02

    Wed

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

    Thu

  • PIT–MDW, 09/04/2026: From $154
    04

    Fri

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

    Sat

  • PIT–MDW, 09/06/2026: From $69
    06

    Sun

  • PIT–MDW, 09/07/2026: From $215
    07

    Mon

  • PIT–MDW, 09/08/2026: From $112
    08

    Tue

  • PIT–MDW, 09/09/2026: From $112
    09

    Wed

  • PIT–MDW, 09/10/2026: From $122
    10

    Thu

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

    Fri

  • PIT–MDW, 09/12/2026: From $112
    12

    Sat

    • Range$69-$279

    *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.

    Explore Flights from Other Popular Origins

    Popular Flights from Pittsburgh