Southwest® flights from Jacksonville to Chicago (Midway) from $117

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Low fares from Jacksonville to Chicago (Midway)

$

Jacksonville (JAX)to

Chicago (Midway) (MDW)
Depart: 04/28/2026

One-way

Basic

From
$117
Seen: 14 hrs ago

Jacksonville (JAX)to

Chicago (Midway) (MDW)
Depart: 04/14/2026

One-way

Basic

From
$117
Seen: 7 hrs ago

Jacksonville (JAX)to

Chicago (Midway) (MDW)
Depart: 04/15/2026

One-way

Basic

From
$117
Seen: 9 hrs ago

Jacksonville (JAX)to

Chicago (Midway) (MDW)
Depart: 05/12/2026

One-way

Basic

From
$117
Seen: 2 hrs ago

Jacksonville (JAX)to

Chicago (Midway) (MDW)
Depart: 04/22/2026

One-way

Basic

From
$117
Seen: 22 hrs ago

Jacksonville (JAX)to

Chicago (Midway) (MDW)
Depart: 05/06/2026

One-way

Basic

From
$117
Seen: 10 hrs ago

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Explore flights from Jacksonville to Chicago (Midway)

Mar 2026
From$252*
Seen: 7 hrs ago
One Way/Basic
Apr 2026
From$117*
Seen: 22 hrs ago
One Way/Basic
May 2026
From$117*
Seen: 44 minutes ago
One Way/Basic
$127
$539
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    • Range$127-$539

    *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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