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

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Low fares from Jacksonville to Chicago-Midway

$

Jacksonville (JAX)to

Chicago-Midway (MDW)
Depart: 10/31/2026

One-way

Basic

From
$164
Seen: 19 hrs ago

Jacksonville (JAX)to

Chicago-Midway (MDW)
Depart: 10/06/2026

One-way

Basic

From
$164
Seen: 15 hrs ago

Jacksonville (JAX)to

Chicago-Midway (MDW)
Depart: 10/07/2026

One-way

Basic

From
$164
Seen: 11 hrs ago

Jacksonville (JAX)to

Chicago-Midway (MDW)
Depart: 11/11/2026

One-way

Basic

From
$164
Seen: 11 hrs ago

Jacksonville (JAX)to

Chicago-Midway (MDW)
Depart: 10/23/2026

One-way

Basic

From
$164
Seen: 18 hrs ago

Jacksonville (JAX)to

Chicago-Midway (MDW)
Depart: 10/17/2026

One-way

Basic

From
$164
Seen: 8 hrs ago

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Explore flights from Jacksonville to Chicago-Midway

Sep 2026
From$257*
Seen: 39 minutes ago
One Way/Basic
Oct 2026
From$164*
Seen: 18 hrs ago
One Way/Basic
Nov 2026
From$164*
Seen: 6 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $164
cmp-daily-histogram-bars-legend-max-price-aria-label $307
Displaying fares for September-2026
  • JAX–MDW, 09/11/2026: From $307
    11

    Fri

    SEP

  • JAX–MDW, 09/12/2026: From $257
    12

    Sat

  • JAX–MDW, 09/13/2026: From $286
    13

    Sun

  • JAX–MDW, 09/14/2026: From $296
    14

    Mon

  • JAX–MDW, 09/15/2026: From $257
    15

    Tue

  • JAX–MDW, 09/16/2026: From $257
    16

    Wed

  • JAX–MDW, 09/17/2026: From $286
    17

    Thu

  • JAX–MDW, 09/18/2026: From $296
    18

    Fri

  • JAX–MDW, 09/19/2026: From $257
    19

    Sat

  • JAX–MDW, 09/20/2026: From $286
    20

    Sun

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

    Mon

  • JAX–MDW, 09/22/2026: From $257
    22

    Tue

  • JAX–MDW, 09/23/2026: From $257
    23

    Wed

  • JAX–MDW, 09/24/2026: From $296
    24

    Thu

  • JAX–MDW, 09/25/2026: From $267
    25

    Fri

  • JAX–MDW, 09/26/2026: From $257
    26

    Sat

  • JAX–MDW, 09/27/2026: From $267
    27

    Sun

  • JAX–MDW, 09/28/2026: From $277
    28

    Mon

  • JAX–MDW, 09/29/2026: From $267
    29

    Tue

  • JAX–MDW, 09/30/2026: From $257
    30

    Wed

  • JAX–MDW: cmp-view-offers-disclaimer. Find Offers
    01

    Thu

    OCT

  • JAX–MDW, 10/02/2026: From $174
    02

    Fri

  • JAX–MDW, 10/03/2026: From $164
    03

    Sat

  • JAX–MDW, 10/04/2026: From $234
    04

    Sun

  • JAX–MDW, 10/05/2026: From $174
    05

    Mon

  • JAX–MDW, 10/06/2026: From $164
    06

    Tue

  • JAX–MDW, 10/07/2026: From $164
    07

    Wed

  • JAX–MDW, 10/08/2026: From $174
    08

    Thu

  • JAX–MDW, 10/09/2026: From $174
    09

    Fri

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

    Sat

    • Range$164-$307

    *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:
    Jacksonville International Airport
    Arriving at:
    Chicago Midway International Airport
    Average flight time:
    2 hours 23 minutes
    Distance:
    849 miles

    Route Information

    150† 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 Jacksonville to Chicago (Midway) is 2 hours 23 minutes.
    There are 150 weekly flights from Jacksonville to Chicago (Midway) on Southwest Airlines.
    Yes, Southwest flies nonstop from Jacksonville to Chicago (Midway) once per day from Monday through Friday.
    Yes, Southwest flies nonstop from Jacksonville to Chicago (Midway) once per day on Saturdays and Sundays.
    To find the lowest fares by day and time to fly Jacksonville 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 Jacksonville 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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