Southwest® flights from Chicago-Midway to Jacksonville from $129

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Low fares from Chicago-Midway to Jacksonville

$

Chicago-Midway (MDW)to

Jacksonville (JAX)
Depart: 01/26/2027

One-way

Basic

From
$129
Seen: 18 hrs ago

Chicago-Midway (MDW)to

Jacksonville (JAX)
Depart: 12/15/2026

One-way

Basic

From
$129
Seen: 10 hrs ago

Chicago-Midway (MDW)to

Jacksonville (JAX)
Depart: 11/11/2026

One-way

Basic

From
$129
Seen: 6 hrs ago

Chicago-Midway (MDW)to

Jacksonville (JAX)
Depart: 11/26/2026

One-way

Basic

From
$129
Seen: 5 hrs ago

Chicago-Midway (MDW)to

Jacksonville (JAX)
Depart: 01/07/2027

One-way

Basic

From
$129
Seen: 5 hrs ago

Chicago-Midway (MDW)to

Jacksonville (JAX)
Depart: 12/14/2026

One-way

Basic

From
$129
Seen: 1 hour ago

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Explore flights from Chicago-Midway to Jacksonville

Oct 2026
From$266*
Seen: 12 hrs ago
One Way/Basic
Nov 2026
From$129*
Seen: 17 hrs ago
One Way/Basic
Dec 2026
From$129*
Seen: 6 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $129
cmp-daily-histogram-bars-legend-max-price-aria-label $316
Displaying fares for October-2026
  • MDW–JAX, 10/22/2026: From $306
    22

    Thu

    OCT

  • MDW–JAX, 10/23/2026: From $306
    23

    Fri

  • MDW–JAX, 10/24/2026: From $267
    24

    Sat

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

    Sun

  • MDW–JAX, 10/26/2026: From $316
    26

    Mon

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

    Tue

  • MDW–JAX, 10/28/2026: From $266
    28

    Wed

  • MDW–JAX, 10/29/2026: From $306
    29

    Thu

  • MDW–JAX, 10/30/2026: From $306
    30

    Fri

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

    Sat

  • MDW–JAX, 11/01/2026: From $306
    01

    Sun

    NOV

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

    Mon

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

    Tue

  • MDW–JAX: cmp-view-offers-disclaimer. Find Offers
    04

    Wed

  • MDW–JAX, 11/05/2026: From $287
    05

    Thu

  • MDW–JAX, 11/06/2026: From $287
    06

    Fri

  • MDW–JAX, 11/07/2026: From $277
    07

    Sat

  • MDW–JAX, 11/08/2026: From $297
    08

    Sun

  • MDW–JAX, 11/09/2026: From $139
    09

    Mon

  • MDW–JAX: cmp-view-offers-disclaimer. Find Offers
    10

    Tue

  • MDW–JAX, 11/11/2026: From $129
    11

    Wed

  • MDW–JAX, 11/12/2026: From $129
    12

    Thu

  • MDW–JAX, 11/13/2026: From $152
    13

    Fri

  • MDW–JAX, 11/14/2026: From $139
    14

    Sat

  • MDW–JAX, 11/15/2026: From $152
    15

    Sun

  • MDW–JAX, 11/16/2026: From $129
    16

    Mon

  • MDW–JAX, 11/17/2026: From $129
    17

    Tue

  • MDW–JAX, 11/18/2026: From $129
    18

    Wed

  • MDW–JAX, 11/19/2026: From $254
    19

    Thu

  • MDW–JAX, 11/20/2026: From $206
    20

    Fri

  • MDW–JAX, 11/21/2026: From $241
    21

    Sat

    • Range$129-$316

    *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

    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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