Southwest® flights from Chicago-Midway to Jacksonville from $164

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Low fares from Chicago-Midway to Jacksonville

$

Chicago-Midway (MDW)to

Jacksonville (JAX)
Depart: 11/04/2026

One-way

Basic

From
$164
Seen: 22 hrs ago

Chicago-Midway (MDW)to

Jacksonville (JAX)
Depart: 10/28/2026

One-way

Basic

From
$164
Seen: 22 hrs ago

Chicago-Midway (MDW)to

Jacksonville (JAX)
Depart: 11/06/2026

One-way

Basic

From
$164
Seen: 23 hrs ago

Chicago-Midway (MDW)to

Jacksonville (JAX)
Depart: 11/10/2026

One-way

Basic

From
$164
Seen: 14 hrs ago

Chicago-Midway (MDW)to

Jacksonville (JAX)
Depart: 10/24/2026

One-way

Basic

From
$164
Seen: 14 hrs ago

Chicago-Midway (MDW)to

Jacksonville (JAX)
Depart: 11/18/2026

One-way

Basic

From
$164
Seen: 12 hrs ago

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Explore flights from Chicago-Midway to Jacksonville

Oct 2026
From$164*
Seen: 22 hrs ago
One Way/Basic
Nov 2026
From$164*
Seen: 8 hrs ago
One Way/Basic
Dec 2026
From$186*
Seen: 14 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $164
cmp-daily-histogram-bars-legend-max-price-aria-label $311
Displaying fares for October-2026
  • MDW–JAX, 10/03/2026: From $267
    03

    Sat

    OCT

  • MDW–JAX, 10/04/2026: From $306
    04

    Sun

  • MDW–JAX, 10/05/2026: From $296
    05

    Mon

  • MDW–JAX, 10/06/2026: From $267
    06

    Tue

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

    Wed

  • MDW–JAX, 10/08/2026: From $296
    08

    Thu

  • MDW–JAX, 10/09/2026: From $311
    09

    Fri

  • MDW–JAX, 10/10/2026: From $267
    10

    Sat

  • MDW–JAX, 10/11/2026: From $306
    11

    Sun

  • MDW–JAX, 10/12/2026: From $296
    12

    Mon

  • MDW–JAX, 10/13/2026: From $267
    13

    Tue

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

    Wed

  • MDW–JAX, 10/15/2026: From $296
    15

    Thu

  • MDW–JAX, 10/16/2026: From $296
    16

    Fri

  • MDW–JAX, 10/17/2026: From $267
    17

    Sat

  • MDW–JAX, 10/18/2026: From $298
    18

    Sun

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

    Mon

  • MDW–JAX, 10/20/2026: From $267
    20

    Tue

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

    Wed

  • MDW–JAX, 10/22/2026: From $277
    22

    Thu

  • MDW–JAX, 10/23/2026: From $164
    23

    Fri

  • MDW–JAX, 10/24/2026: From $164
    24

    Sat

  • MDW–JAX, 10/25/2026: From $254
    25

    Sun

  • MDW–JAX, 10/26/2026: From $164
    26

    Mon

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

    Tue

  • MDW–JAX, 10/28/2026: From $164
    28

    Wed

  • MDW–JAX, 10/29/2026: From $164
    29

    Thu

  • MDW–JAX, 10/30/2026: From $164
    30

    Fri

  • MDW–JAX, 10/31/2026: From $164
    31

    Sat

  • MDW–JAX, 11/01/2026: From $164
    01

    Sun

    NOV

  • MDW–JAX, 11/02/2026: From $164
    02

    Mon

    • Range$164-$311

    *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:
    Jacksonville International Airport
    Average flight time:
    2 hours 10 minutes
    Distance:
    849 miles

    Route Information

    142† Weekly flights
    • 1‡ Nonstop flight per day Monday through Friday
    • 1‡ Nonstop flight on Saturday
    • 1‡ Nonstop flight on Sunday

    † 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

    The average flight time from Chicago (Midway) to Jacksonville is 2 hours 10 minutes.
    There are 142 weekly flights from Chicago (Midway) to Jacksonville on Southwest Airlines.
    Yes, Southwest flies nonstop from Chicago (Midway) to Jacksonville once per day from Monday through Friday.
    Yes, Southwest flies nonstop from Chicago (Midway) to Jacksonville once per day on Saturdays and Sundays.
    To find the lowest fares by day and time to fly Chicago (Midway) to Jacksonville with Southwest, check out our Low Fare Calendar.
    You can rent a car at Jacksonville International Airport book yours with your flight.
    Yes! Flights from Chicago (Midway) to Jacksonville—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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