Southwest® flights from Chicago-Midway to Jacksonville from $195

Promo Code

Low fares from Chicago-Midway to Jacksonville

$

Chicago-Midway (MDW)to

Jacksonville (JAX)
Depart: 12/08/2026

One-way

Basic

From
$195
Seen: 18 hrs ago

Chicago-Midway (MDW)to

Jacksonville (JAX)
Depart: 01/26/2027

One-way

Basic

From
$195
Seen: 7 hrs ago

Chicago-Midway (MDW)to

Jacksonville (JAX)
Depart: 12/15/2026

One-way

Basic

From
$195
Seen: 4 hrs ago

Chicago-Midway (MDW)to

Jacksonville (JAX)
Depart: 02/10/2027

One-way

Basic

From
$195
Seen: 54 minutes ago

Chicago-Midway (MDW)to

Jacksonville (JAX)
Depart: 12/09/2026

One-way

Basic

From
$195
Seen: 21 hrs ago

Chicago-Midway (MDW)to

Jacksonville (JAX)
Depart: 12/22/2026

One-way

Basic

From
$195
Seen: 16 hrs ago

Looking for more low-fare flights?

Check out the Low Fare Calendar to find a fare that works for you. Just choose the month you want to depart and return, and we’ll show you the best fares available.

Find low fares

Explore flights from Chicago-Midway to Jacksonville

Nov 2026
From$260*
Seen: 11 hrs ago
One Way/Basic
Dec 2026
From$195*
Seen: 21 hrs ago
One Way/Basic
Jan 2027
From$195*
Seen: 22 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $195
cmp-daily-histogram-bars-legend-max-price-aria-label $270
Displaying fares for November-2026
  • MDW–JAX, 11/13/2026: From $260
    13

    Fri

    NOV

  • MDW–JAX, 11/14/2026: From $270
    14

    Sat

  • MDW–JAX, 11/15/2026: From $260
    15

    Sun

  • MDW–JAX, 11/16/2026: From $260
    16

    Mon

  • MDW–JAX: cmp-view-offers-disclaimer. Find Offers
    17

    Tue

  • MDW–JAX, 11/18/2026: From $260
    18

    Wed

  • MDW–JAX, 11/19/2026: From $260
    19

    Thu

  • MDW–JAX, 11/20/2026: From $260
    20

    Fri

  • MDW–JAX, 11/21/2026: From $260
    21

    Sat

  • MDW–JAX, 11/22/2026: From $260
    22

    Sun

  • MDW–JAX, 11/23/2026: From $260
    23

    Mon

  • MDW–JAX, 11/24/2026: From $260
    24

    Tue

  • MDW–JAX, 11/25/2026: From $260
    25

    Wed

  • MDW–JAX, 11/26/2026: From $260
    26

    Thu

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

    Fri

  • MDW–JAX, 11/28/2026: From $260
    28

    Sat

  • MDW–JAX, 11/29/2026: From $260
    29

    Sun

  • MDW–JAX, 11/30/2026: From $260
    30

    Mon

  • MDW–JAX, 12/01/2026: From $260
    01

    Tue

    DEC

  • MDW–JAX, 12/02/2026: From $195
    02

    Wed

  • MDW–JAX, 12/03/2026: From $215
    03

    Thu

  • MDW–JAX, 12/04/2026: From $230
    04

    Fri

  • MDW–JAX, 12/05/2026: From $205
    05

    Sat

  • MDW–JAX, 12/06/2026: From $259
    06

    Sun

  • MDW–JAX: cmp-view-offers-disclaimer. Find Offers
    07

    Mon

  • MDW–JAX, 12/08/2026: From $195
    08

    Tue

  • MDW–JAX, 12/09/2026: From $195
    09

    Wed

  • MDW–JAX, 12/10/2026: From $215
    10

    Thu

  • MDW–JAX, 12/11/2026: From $211
    11

    Fri

  • MDW–JAX: cmp-view-offers-disclaimer. Find Offers
    12

    Sat

    • Range$195-$270

    *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.

    Explore Flights from Other Popular Origins

    Popular Flights from Chicago-Midway