Southwest® flights from Jacksonville to Chicago (O'Hare)

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Low fares from Jacksonville to Chicago (O'Hare)

$

Jacksonville (JAX)to

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

One-way

Basic

From
$99
Seen: 23 hrs ago

Jacksonville (JAX)to

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

One-way

Basic

From
$99
Seen: 21 hrs ago

Jacksonville (JAX)to

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

One-way

Basic

From
$99
Seen: 21 hrs ago

Jacksonville (JAX)to

Chicago (Midway) (MDW)
Depart: 11/09/2026

One-way

Basic

From
$99
Seen: 15 hrs ago

Jacksonville (JAX)to

Chicago (Midway) (MDW)
Depart: 11/23/2026

One-way

Basic

From
$99
Seen: 14 hrs ago

Jacksonville (JAX)to

Chicago (Midway) (MDW)
Depart: 09/22/2026

One-way

Basic

From
$99
Seen: 23 hrs ago

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Explore flights from Jacksonville to Chicago (O'Hare)

Aug 2026
From$247*
Seen: 2 hrs ago
One Way/Basic
Sep 2026
From$99*
Seen: 22 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 $99
cmp-daily-histogram-bars-legend-max-price-aria-label $276
Displaying fares for August-2026
  • JAX–MDW: cmp-view-offers-disclaimer. Find Offers
    24

    Mon

    AUG

  • JAX–MDW, 08/25/2026: From $247
    25

    Tue

  • JAX–MDW, 08/26/2026: From $247
    26

    Wed

  • JAX–MDW, 08/27/2026: From $276
    27

    Thu

  • JAX–MDW, 08/28/2026: From $276
    28

    Fri

  • JAX–MDW: cmp-view-offers-disclaimer. Find Offers
    29

    Sat

  • JAX–MDW, 08/30/2026: From $276
    30

    Sun

  • JAX–MDW, 08/31/2026: From $276
    31

    Mon

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

    Tue

    SEP

  • JAX–MDW, 09/02/2026: From $247
    02

    Wed

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

    Thu

  • JAX–MDW, 09/04/2026: From $276
    04

    Fri

  • JAX–MDW, 09/05/2026: From $203
    05

    Sat

  • JAX–MDW: cmp-view-offers-disclaimer. Find Offers
    06

    Sun

  • JAX–MDW, 09/07/2026: From $257
    07

    Mon

  • JAX–MDW, 09/08/2026: From $247
    08

    Tue

  • JAX–MDW: cmp-view-offers-disclaimer. Find Offers
    09

    Wed

  • JAX–MDW, 09/10/2026: From $193
    10

    Thu

  • JAX–MDW, 09/11/2026: From $203
    11

    Fri

  • JAX–MDW, 09/12/2026: From $193
    12

    Sat

  • JAX–MDW, 09/13/2026: From $144
    13

    Sun

  • JAX–MDW, 09/14/2026: From $109
    14

    Mon

  • JAX–MDW, 09/15/2026: From $99
    15

    Tue

  • JAX–MDW: cmp-view-offers-disclaimer. Find Offers
    16

    Wed

  • JAX–MDW, 09/17/2026: From $154
    17

    Thu

  • JAX–MDW, 09/18/2026: From $154
    18

    Fri

  • JAX–MDW, 09/19/2026: From $99
    19

    Sat

  • JAX–MDW, 09/20/2026: From $154
    20

    Sun

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

    Mon

  • JAX–MDW, 09/22/2026: From $99
    22

    Tue

  • JAX–MDW, 09/23/2026: From $99
    23

    Wed

    • Range$99-$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:
    O'Hare International Airport
    Distance:
    864 miles

    Route Information

    56† Weekly flights

    † 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

    There are 56 weekly flights from Jacksonville to Chicago (O'Hare) on Southwest Airlines.
    To find the lowest fares by day and time to fly Jacksonville to Chicago (O'Hare) with Southwest, check out our Low Fare Calendar.
    You can rent a car at O'Hare International Airport book yours with your flight.
    Yes! Flights from Jacksonville to Chicago (O'Hare)—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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