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

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Low fares from Pensacola to Chicago (O'Hare)

$

Pensacola (PNS)to

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

One-way

Basic

From
$145
Seen: 15 hrs ago

Pensacola (PNS)to

Chicago (Midway) (MDW)
Depart: 10/26/2026

One-way

Basic

From
$150
Seen: 22 hrs ago

Pensacola (PNS)to

Chicago (Midway) (MDW)
Depart: 10/02/2026

One-way

Basic

From
$150
Seen: 16 hrs ago

Pensacola (PNS)to

Chicago (Midway) (MDW)
Depart: 10/19/2026

One-way

Basic

From
$150
Seen: 14 hrs ago

Pensacola (PNS)to

Chicago (Midway) (MDW)
Depart: 09/28/2026

One-way

Basic

From
$150
Seen: 14 hrs ago

Pensacola (PNS)to

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

One-way

Basic

From
$150
Seen: 19 hrs ago

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Explore flights from Pensacola to Chicago (O'Hare)

Aug 2026
From$205*
Seen: 22 hrs ago
One Way/Basic
Sep 2026
From$145*
Seen: 15 hrs ago
One Way/Basic
Oct 2026
From$150*
Seen: 14 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $145
cmp-daily-histogram-bars-legend-max-price-aria-label $411
Displaying fares for August-2026
  • PNS–MDW, 08/25/2026: From $262
    25

    Tue

    AUG

  • PNS–MDW, 08/26/2026: From $262
    26

    Wed

  • PNS–MDW, 08/27/2026: From $265
    27

    Thu

  • PNS–MDW: cmp-view-offers-disclaimer. Find Offers
    28

    Fri

  • PNS–MDW, 08/29/2026: From $257
    29

    Sat

  • PNS–MDW, 08/30/2026: From $265
    30

    Sun

  • PNS–MDW, 08/31/2026: From $205
    31

    Mon

  • PNS–MDW, 09/01/2026: From $205
    01

    Tue

    SEP

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

    Wed

  • PNS–MDW: cmp-view-offers-disclaimer. Find Offers
    03

    Thu

  • PNS–MDW, 09/04/2026: From $205
    04

    Fri

  • PNS–MDW, 09/05/2026: From $193
    05

    Sat

  • PNS–MDW, 09/06/2026: From $193
    06

    Sun

  • PNS–MDW, 09/07/2026: From $411
    07

    Mon

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

    Tue

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

    Wed

  • PNS–MDW, 09/10/2026: From $170
    10

    Thu

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

    Fri

  • PNS–MDW, 09/12/2026: From $170
    12

    Sat

  • PNS–MDW, 09/13/2026: From $170
    13

    Sun

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

    Mon

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

    Tue

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

    Wed

  • PNS–MDW, 09/17/2026: From $155
    17

    Thu

  • PNS–MDW, 09/18/2026: From $155
    18

    Fri

  • PNS–MDW, 09/19/2026: From $145
    19

    Sat

  • PNS–MDW, 09/20/2026: From $189
    20

    Sun

  • PNS–MDW, 09/21/2026: From $170
    21

    Mon

  • PNS–MDW, 09/22/2026: From $150
    22

    Tue

  • PNS–MDW, 09/23/2026: From $150
    23

    Wed

  • PNS–MDW, 09/24/2026: From $150
    24

    Thu

    • Range$145-$411

    *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:
    O'Hare International Airport
    Distance:
    794 miles

    Route Information

    45† 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 45 weekly flights from Pensacola to Chicago (O'Hare) on Southwest Airlines.
    To find the lowest fares by day and time to fly Pensacola 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 Pensacola 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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