Southwest® flights from Pensacola to Chicago-Midway from $176

Promo Code

Low fares from Pensacola to Chicago-Midway

$

Pensacola (PNS)to

Chicago-Midway (MDW)
Depart: 12/15/2026

One-way

Basic

From
$176
Seen: 21 hrs ago

Pensacola (PNS)to

Chicago-Midway (MDW)
Depart: 12/22/2026

One-way

Basic

From
$181
Seen: 17 hrs ago

Pensacola (PNS)to

Chicago-Midway (MDW)
Depart: 12/02/2026

One-way

Basic

From
$181
Seen: 7 hrs ago

Pensacola (PNS)to

Chicago-Midway (MDW)
Depart: 12/05/2026

One-way

Basic

From
$181
Seen: 9 hrs ago

Pensacola (PNS)to

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

One-way

Basic

From
$181
Seen: 6 hrs ago

Pensacola (PNS)to

Chicago-Midway (MDW)
Depart: 12/08/2026

One-way

Basic

From
$181
Seen: 12 hrs ago

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Explore flights from Pensacola to Chicago-Midway

Nov 2026
From$205*
Seen: 18 hrs ago
One Way/Basic
Dec 2026
From$176*
Seen: 21 hrs ago
One Way/Basic
Jan 2027
From$185*
Seen: 1 hour ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $181
cmp-daily-histogram-bars-legend-max-price-aria-label $484
Displaying fares for November-2026
  • PNS–MDW, 11/11/2026: From $297
    11

    Wed

    NOV

  • PNS–MDW, 11/12/2026: From $300
    12

    Thu

  • PNS–MDW: cmp-view-offers-disclaimer. Find Offers
    13

    Fri

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

    Sat

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

    Sun

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

    Mon

  • PNS–MDW, 11/17/2026: From $297
    17

    Tue

  • PNS–MDW, 11/18/2026: From $240
    18

    Wed

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

    Thu

  • PNS–MDW, 11/20/2026: From $245
    20

    Fri

  • PNS–MDW, 11/21/2026: From $240
    21

    Sat

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

    Sun

  • PNS–MDW, 11/23/2026: From $240
    23

    Mon

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

    Tue

  • PNS–MDW, 11/25/2026: From $308
    25

    Wed

  • PNS–MDW, 11/26/2026: From $205
    26

    Thu

  • PNS–MDW, 11/27/2026: From $319
    27

    Fri

  • PNS–MDW, 11/28/2026: From $484
    28

    Sat

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

    Sun

  • PNS–MDW, 11/30/2026: From $230
    30

    Mon

  • PNS–MDW, 12/01/2026: From $210
    01

    Tue

    DEC

  • PNS–MDW, 12/02/2026: From $181
    02

    Wed

  • PNS–MDW, 12/03/2026: From $185
    03

    Thu

  • PNS–MDW, 12/04/2026: From $185
    04

    Fri

  • PNS–MDW, 12/05/2026: From $181
    05

    Sat

  • PNS–MDW, 12/06/2026: From $185
    06

    Sun

  • PNS–MDW, 12/07/2026: From $206
    07

    Mon

  • PNS–MDW, 12/08/2026: From $181
    08

    Tue

  • PNS–MDW, 12/09/2026: From $181
    09

    Wed

  • PNS–MDW, 12/10/2026: From $185
    10

    Thu

    • Range$181-$484

    *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

    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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