Southwest® flights from Chicago-Midway to Pensacola from $160

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Low fares from Chicago-Midway to Pensacola

$

Chicago-Midway (MDW)to

Pensacola (PNS)
Depart: 11/09/2026

One-way

Basic

From
$160
Seen: 12 hrs ago

Chicago-Midway (MDW)to

Pensacola (PNS)
Depart: 09/30/2026

One-way

Basic

From
$160
Seen: 6 hrs ago

Chicago-Midway (MDW)to

Pensacola (PNS)
Depart: 10/21/2026

One-way

Basic

From
$160
Seen: 8 hrs ago

Chicago-Midway (MDW)to

Pensacola (PNS)
Depart: 11/26/2026

One-way

Basic

From
$160
Seen: 6 hrs ago

Chicago-Midway (MDW)to

Pensacola (PNS)
Depart: 11/10/2026

One-way

Basic

From
$160
Seen: 45 minutes ago

Chicago-Midway (MDW)to

Pensacola (PNS)
Depart: 10/05/2026

One-way

Basic

From
$160
Seen: 21 hrs ago

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Explore flights from Chicago-Midway to Pensacola

Sep 2026
From$160*
Seen: 6 hrs ago
One Way/Basic
Oct 2026
From$160*
Seen: 21 hrs ago
One Way/Basic
Nov 2026
From$160*
Seen: 1 hour ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $160
cmp-daily-histogram-bars-legend-max-price-aria-label $301
Displaying fares for September-2026
  • MDW–PNS, 09/11/2026: From $275
    11

    Fri

    SEP

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

    Sat

  • MDW–PNS, 09/13/2026: From $275
    13

    Sun

  • MDW–PNS, 09/14/2026: From $275
    14

    Mon

  • MDW–PNS, 09/15/2026: From $267
    15

    Tue

  • MDW–PNS, 09/16/2026: From $210
    16

    Wed

  • MDW–PNS, 09/17/2026: From $265
    17

    Thu

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

    Fri

  • MDW–PNS, 09/19/2026: From $215
    19

    Sat

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

    Sun

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

    Mon

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

    Tue

  • MDW–PNS, 09/23/2026: From $175
    23

    Wed

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

    Thu

  • MDW–PNS, 09/25/2026: From $180
    25

    Fri

  • MDW–PNS, 09/26/2026: From $180
    26

    Sat

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

    Sun

  • MDW–PNS, 09/28/2026: From $180
    28

    Mon

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

    Tue

  • MDW–PNS, 09/30/2026: From $160
    30

    Wed

  • MDW–PNS, 10/01/2026: From $295
    01

    Thu

    OCT

  • MDW–PNS: cmp-view-offers-disclaimer. Find Offers
    02

    Fri

  • MDW–PNS, 10/03/2026: From $204
    03

    Sat

  • MDW–PNS, 10/04/2026: From $274
    04

    Sun

  • MDW–PNS, 10/05/2026: From $160
    05

    Mon

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

    Tue

  • MDW–PNS, 10/07/2026: From $239
    07

    Wed

  • MDW–PNS, 10/08/2026: From $301
    08

    Thu

  • MDW–PNS, 10/09/2026: From $295
    09

    Fri

  • MDW–PNS, 10/10/2026: From $261
    10

    Sat

    • Range$160-$301

    *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:
    Pensacola International Airport
    Distance:
    781 miles

    Route Information

    99† 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 99 weekly flights from Chicago (Midway) to Pensacola on Southwest Airlines.
    To find the lowest fares by day and time to fly Chicago (Midway) to Pensacola with Southwest, check out our Low Fare Calendar.
    You can rent a car at Pensacola International Airport book yours with your flight.
    Yes! Flights from Chicago (Midway) to Pensacola—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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