Southwest® flights from Pensacola to Chicago (Midway) from $144

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Low fares from Pensacola to Chicago (Midway)

$

Pensacola (PNS)to

Chicago (Midway) (MDW)
Depart: 09/19/2026

One-way

Basic

From
$144
Seen: 23 hrs ago

Pensacola (PNS)to

Chicago (Midway) (MDW)
Depart: 09/26/2026

One-way

Basic

From
$145
Seen: 21 hrs ago

Pensacola (PNS)to

Chicago (Midway) (MDW)
Depart: 10/05/2026

One-way

Basic

From
$149
Seen: 23 hrs ago

Pensacola (PNS)to

Chicago (Midway) (MDW)
Depart: 09/12/2026

One-way

Basic

From
$149
Seen: 22 hrs ago

Pensacola (PNS)to

Chicago (Midway) (MDW)
Depart: 09/23/2026

One-way

Basic

From
$149
Seen: 22 hrs ago

Pensacola (PNS)to

Chicago (Midway) (MDW)
Depart: 10/06/2026

One-way

Basic

From
$149
Seen: 23 hrs ago

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Explore flights from Pensacola to Chicago (Midway)

Aug 2026
From$150*
Seen: 9 hrs ago
One Way/Basic
Sep 2026
From$144*
Seen: 23 hrs ago
One Way/Basic
Oct 2026
From$149*
Seen: 33 minutes ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $150
cmp-daily-histogram-bars-legend-max-price-aria-label $265
Displaying fares for August-2026
  • PNS–MDW, 08/01/2026: From $262
    01

    Sat

    AUG

  • PNS–MDW, 08/02/2026: From $255
    02

    Sun

  • PNS–MDW, 08/03/2026: From $255
    03

    Mon

  • PNS–MDW, 08/04/2026: From $262
    04

    Tue

  • PNS–MDW, 08/05/2026: From $262
    05

    Wed

  • PNS–MDW, 08/06/2026: From $265
    06

    Thu

  • PNS–MDW, 08/07/2026: From $205
    07

    Fri

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

    Sat

  • PNS–MDW, 08/09/2026: From $260
    09

    Sun

  • PNS–MDW, 08/10/2026: From $205
    10

    Mon

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

    Tue

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

    Wed

  • PNS–MDW, 08/13/2026: From $205
    13

    Thu

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

    Fri

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

    Sat

  • PNS–MDW: cmp-view-offers-disclaimer. Find Offers
    16

    Sun

  • PNS–MDW, 08/17/2026: From $170
    17

    Mon

  • PNS–MDW: cmp-view-offers-disclaimer. Find Offers
    18

    Tue

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

    Wed

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

    Thu

  • PNS–MDW: cmp-view-offers-disclaimer. Find Offers
    21

    Fri

  • PNS–MDW, 08/22/2026: From $150
    22

    Sat

  • PNS–MDW, 08/23/2026: From $170
    23

    Sun

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

    Mon

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

    Tue

  • PNS–MDW, 08/26/2026: From $150
    26

    Wed

  • PNS–MDW, 08/27/2026: From $150
    27

    Thu

  • PNS–MDW, 08/28/2026: From $150
    28

    Fri

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

    Sat

  • PNS–MDW: cmp-view-offers-disclaimer. Find Offers
    30

    Sun

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

    Mon

    • Range$150-$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:
    Pensacola International Airport
    Arriving at:
    Chicago Midway International Airport
    Distance:
    781 miles

    Route Information

    91† 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 91 weekly flights from Pensacola to Chicago (Midway) on Southwest Airlines.
    To find the lowest fares by day and time to fly Pensacola 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 Pensacola 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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