Southwest® flights from Pittsburgh to Chicago (O'Hare)

Promo Code

Low fares from Pittsburgh to Chicago (O'Hare)

$

Pittsburgh (PIT)to

Chicago (Midway) (MDW)
Depart: 09/15/2026

One-way

Basic

From
$69
Seen: 21 hrs ago

Pittsburgh (PIT)to

Chicago (Midway) (MDW)
Depart: 12/01/2026

One-way

Basic

From
$69
Seen: 21 hrs ago

Pittsburgh (PIT)to

Chicago (Midway) (MDW)
Depart: 09/21/2026

One-way

Basic

From
$69
Seen: 15 hrs ago

Pittsburgh (PIT)to

Chicago (Midway) (MDW)
Depart: 09/17/2026

One-way

Basic

From
$69
Seen: 13 hrs ago

Pittsburgh (PIT)to

Chicago (Midway) (MDW)
Depart: 10/08/2026

One-way

Basic

From
$69
Seen: 12 hrs ago

Pittsburgh (PIT)to

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

One-way

Basic

From
$69
Seen: 17 hrs ago

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Explore flights from Pittsburgh to Chicago (O'Hare)

Aug 2026
From$250*
Seen: 23 hrs ago
One Way/Basic
Sep 2026
From$69*
Seen: 15 hrs ago
One Way/Basic
Oct 2026
From$69*
Seen: 23 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, 08/25/2026: From $250
    25

    Tue

    AUG

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

    Wed

  • PIT–MDW, 08/27/2026: From $279
    27

    Thu

  • PIT–MDW, 08/28/2026: From $279
    28

    Fri

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

    Sat

  • PIT–MDW, 08/30/2026: From $279
    30

    Sun

  • PIT–MDW, 08/31/2026: From $279
    31

    Mon

  • PIT–MDW, 09/01/2026: From $250
    01

    Tue

    SEP

  • PIT–MDW, 09/02/2026: From $250
    02

    Wed

  • PIT–MDW, 09/03/2026: From $279
    03

    Thu

  • PIT–MDW, 09/04/2026: From $279
    04

    Fri

  • PIT–MDW, 09/05/2026: From $200
    05

    Sat

  • PIT–MDW, 09/06/2026: From $200
    06

    Sun

  • PIT–MDW, 09/07/2026: From $255
    07

    Mon

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

    Tue

  • PIT–MDW, 09/09/2026: From $200
    09

    Wed

  • PIT–MDW, 09/10/2026: From $200
    10

    Thu

  • PIT–MDW, 09/11/2026: From $200
    11

    Fri

  • PIT–MDW, 09/12/2026: From $200
    12

    Sat

  • PIT–MDW, 09/13/2026: From $255
    13

    Sun

  • PIT–MDW: cmp-view-offers-disclaimer. Find Offers
    14

    Mon

  • PIT–MDW, 09/15/2026: From $69
    15

    Tue

  • PIT–MDW, 09/16/2026: From $69
    16

    Wed

  • PIT–MDW, 09/17/2026: From $69
    17

    Thu

  • PIT–MDW, 09/18/2026: From $96
    18

    Fri

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

    Sat

  • PIT–MDW, 09/20/2026: From $215
    20

    Sun

  • PIT–MDW, 09/21/2026: From $69
    21

    Mon

  • PIT–MDW, 09/22/2026: From $69
    22

    Tue

  • PIT–MDW, 09/23/2026: From $69
    23

    Wed

  • PIT–MDW, 09/24/2026: From $69
    24

    Thu

    • 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:
    O'Hare International Airport
    Distance:
    413 miles

    Route Information

    20† Weekly flights

    † 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

    There are 20 weekly flights from Pittsburgh to Chicago (O'Hare) on Southwest Airlines.
    To find the lowest fares by day and time to fly Pittsburgh to Chicago (O'Hare) with Southwest, check out our Low Fare Calendar.
    You can rent a car at O'Hare International Airport book yours with your flight.
    Yes! Flights from Pittsburgh to Chicago (O'Hare)—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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