Southwest® flights from Jacksonville to Chicago (Midway) from $99

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Low fares from Jacksonville to Chicago (Midway)

$

Jacksonville (JAX)to

Chicago (Midway) (MDW)
Depart: 09/06/2026

One-way

Basic

From
$99
Seen: 3 hrs ago

Jacksonville (JAX)to

Chicago (Midway) (MDW)
Depart: 10/30/2026

One-way

Basic

From
$99
Seen: 6 hrs ago

Jacksonville (JAX)to

Chicago (Midway) (MDW)
Depart: 10/30/2026

One-way

Choice

From
$139
Seen: 6 hrs ago

Jacksonville (JAX)to

Chicago (Midway) (MDW)
Depart: 09/06/2026

One-way

Choice

From
$139
Seen: 3 hrs ago

Jacksonville (JAX)to

Chicago (Midway) (MDW)
Depart: 08/26/2026

One-way

Basic

From
$153
Seen: 22 hrs ago

Jacksonville (JAX)to

Chicago (Midway) (MDW)
Depart: 09/26/2026

One-way

Basic

From
$153
Seen: 9 hrs ago

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Explore flights from Jacksonville to Chicago (Midway)

Aug 2026
From$153*
Seen: 3 hrs ago
One Way/Basic
Sep 2026
From$99*
Seen: 3 hrs ago
One Way/Basic
Oct 2026
From$99*
Seen: 6 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $153
cmp-daily-histogram-bars-legend-max-price-aria-label $276
Displaying fares for August-2026
  • JAX–MDW, 08/02/2026: From $276
    02

    Sun

    AUG

  • JAX–MDW, 08/03/2026: From $276
    03

    Mon

  • JAX–MDW, 08/04/2026: From $247
    04

    Tue

  • JAX–MDW, 08/05/2026: From $247
    05

    Wed

  • JAX–MDW, 08/06/2026: From $276
    06

    Thu

  • JAX–MDW, 08/07/2026: From $276
    07

    Fri

  • JAX–MDW, 08/08/2026: From $247
    08

    Sat

  • JAX–MDW, 08/09/2026: From $276
    09

    Sun

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

    Mon

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

    Tue

  • JAX–MDW, 08/12/2026: From $247
    12

    Wed

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

    Thu

  • JAX–MDW, 08/14/2026: From $257
    14

    Fri

  • JAX–MDW, 08/15/2026: From $257
    15

    Sat

  • JAX–MDW, 08/16/2026: From $257
    16

    Sun

  • JAX–MDW, 08/17/2026: From $257
    17

    Mon

  • JAX–MDW: cmp-view-offers-disclaimer. Find Offers
    18

    Tue

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

    Wed

  • JAX–MDW, 08/20/2026: From $257
    20

    Thu

  • JAX–MDW, 08/21/2026: From $184
    21

    Fri

  • JAX–MDW, 08/22/2026: From $153
    22

    Sat

  • JAX–MDW: cmp-view-offers-disclaimer. Find Offers
    23

    Sun

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

    Mon

  • JAX–MDW, 08/25/2026: From $153
    25

    Tue

  • JAX–MDW, 08/26/2026: From $153
    26

    Wed

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

    Thu

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

    Fri

  • JAX–MDW, 08/29/2026: From $153
    29

    Sat

  • JAX–MDW: cmp-view-offers-disclaimer. Find Offers
    30

    Sun

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

    Mon

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

    Tue

    SEP

    • Range$153-$276

    *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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