Southwest® flights from Chicago (Midway) to Pensacola from $145

Promo Code

Low fares from Chicago (Midway) to Pensacola

$

Chicago (Midway) (MDW)to

Pensacola (PNS)
Depart: 09/16/2026

One-way

Basic

From
$145
Seen: 2 hrs ago

Chicago (Midway) (MDW)to

Pensacola (PNS)
Depart: 10/29/2026

One-way

Basic

From
$150
Seen: 23 hrs ago

Chicago (Midway) (MDW)to

Pensacola (PNS)
Depart: 09/21/2026

One-way

Basic

From
$150
Seen: 5 hrs ago

Chicago (Midway) (MDW)to

Pensacola (PNS)
Depart: 10/06/2026

One-way

Basic

From
$150
Seen: 6 hrs ago

Chicago (Midway) (MDW)to

Pensacola (PNS)
Depart: 09/26/2026

One-way

Basic

From
$150
Seen: 19 hrs ago

Chicago (Midway) (MDW)to

Pensacola (PNS)
Depart: 11/11/2026

One-way

Basic

From
$150
Seen: 20 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 Chicago (Midway) to Pensacola

Aug 2026
From$205*
Seen: 18 hrs ago
One Way/Basic
Sep 2026
From$145*
Seen: 2 hrs ago
One Way/Basic
Oct 2026
From$150*
Seen: 18 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $145
cmp-daily-histogram-bars-legend-max-price-aria-label $265
Displaying fares for August-2026
  • MDW–PNS: cmp-view-offers-disclaimer. Find Offers
    22

    Sat

    AUG

  • MDW–PNS, 08/23/2026: From $265
    23

    Sun

  • MDW–PNS, 08/24/2026: From $265
    24

    Mon

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

    Tue

  • MDW–PNS, 08/26/2026: From $257
    26

    Wed

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

    Thu

  • MDW–PNS, 08/28/2026: From $205
    28

    Fri

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

    Sat

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

    Sun

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

    Mon

  • MDW–PNS, 09/01/2026: From $200
    01

    Tue

    SEP

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

    Wed

  • MDW–PNS, 09/03/2026: From $170
    03

    Thu

  • MDW–PNS, 09/04/2026: From $259
    04

    Fri

  • MDW–PNS, 09/05/2026: From $170
    05

    Sat

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

    Sun

  • MDW–PNS: cmp-view-offers-disclaimer. Find Offers
    07

    Mon

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

    Tue

  • MDW–PNS: cmp-view-offers-disclaimer. Find Offers
    09

    Wed

  • MDW–PNS, 09/10/2026: From $150
    10

    Thu

  • MDW–PNS, 09/11/2026: From $150
    11

    Fri

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

    Sat

  • MDW–PNS, 09/13/2026: From $205
    13

    Sun

  • MDW–PNS, 09/14/2026: From $150
    14

    Mon

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

    Tue

  • MDW–PNS, 09/16/2026: From $145
    16

    Wed

  • MDW–PNS, 09/17/2026: From $189
    17

    Thu

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

    Fri

  • MDW–PNS, 09/19/2026: From $155
    19

    Sat

  • MDW–PNS, 09/20/2026: From $170
    20

    Sun

  • MDW–PNS, 09/21/2026: From $150
    21

    Mon

    • Range$145-$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:
    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.

    Explore Flights from Other Popular Origins

    Popular Flights from Chicago (Midway)