Southwest® flights from Chicago-Midway to Jackson from $189

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Low fares from Chicago-Midway to Jackson

$

Chicago-Midway (MDW)to

Jackson (JAN)
Depart: 10/21/2026

One-way

Basic

From
$189
Seen: 12 hrs ago

Chicago-Midway (MDW)to

Jackson (JAN)
Depart: 10/02/2026

One-way

Basic

From
$189
Seen: 21 hrs ago

Chicago-Midway (MDW)to

Jackson (JAN)
Depart: 10/29/2026

One-way

Basic

From
$189
Seen: 21 hrs ago

Chicago-Midway (MDW)to

Jackson (JAN)
Depart: 10/28/2026

One-way

Basic

From
$189
Seen: 23 hrs ago

Chicago-Midway (MDW)to

Jackson (JAN)
Depart: 10/14/2026

One-way

Basic

From
$189
Seen: 22 hrs ago

Chicago-Midway (MDW)to

Jackson (JAN)
Depart: 12/10/2026

One-way

Basic

From
$189
Seen: 19 hrs ago

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Explore flights from Chicago-Midway to Jackson

Sep 2026
From$249*
Seen: 2 hrs ago
One Way/Basic
Oct 2026
From$189*
Seen: 8 hrs ago
One Way/Basic
Nov 2026
From$189*
Seen: 12 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $189
cmp-daily-histogram-bars-legend-max-price-aria-label $551
Displaying fares for September-2026
  • MDW–JAN, 09/12/2026: From $289
    12

    Sat

    SEP

  • MDW–JAN, 09/13/2026: From $551
    13

    Sun

  • MDW–JAN: cmp-view-offers-disclaimer. Find Offers
    14

    Mon

  • MDW–JAN: cmp-view-offers-disclaimer. Find Offers
    15

    Tue

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

    Wed

  • MDW–JAN, 09/17/2026: From $358
    17

    Thu

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

    Fri

  • MDW–JAN, 09/19/2026: From $284
    19

    Sat

  • MDW–JAN, 09/20/2026: From $344
    20

    Sun

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

    Mon

  • MDW–JAN, 09/22/2026: From $282
    22

    Tue

  • MDW–JAN, 09/23/2026: From $282
    23

    Wed

  • MDW–JAN, 09/24/2026: From $344
    24

    Thu

  • MDW–JAN, 09/25/2026: From $335
    25

    Fri

  • MDW–JAN, 09/26/2026: From $249
    26

    Sat

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

    Sun

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

    Mon

  • MDW–JAN, 09/29/2026: From $249
    29

    Tue

  • MDW–JAN, 09/30/2026: From $249
    30

    Wed

  • MDW–JAN, 10/01/2026: From $254
    01

    Thu

    OCT

  • MDW–JAN, 10/02/2026: From $189
    02

    Fri

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

    Sat

  • MDW–JAN, 10/04/2026: From $275
    04

    Sun

  • MDW–JAN, 10/05/2026: From $236
    05

    Mon

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

    Tue

  • MDW–JAN, 10/07/2026: From $199
    07

    Wed

  • MDW–JAN, 10/08/2026: From $284
    08

    Thu

  • MDW–JAN, 10/09/2026: From $340
    09

    Fri

  • MDW–JAN, 10/10/2026: From $270
    10

    Sat

  • MDW–JAN, 10/11/2026: From $349
    11

    Sun

    • Range$189-$551

    *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:
    Jackson-Evers International Airport
    Distance:
    666 miles

    Route Information

    70† 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 70 weekly flights from Chicago (Midway) to Jackson on Southwest Airlines.
    To find the lowest fares by day and time to fly Chicago (Midway) to Jackson with Southwest, check out our Low Fare Calendar.
    You can rent a car at Jackson-Evers International Airport book yours with your flight.
    Yes! Flights from Chicago (Midway) to Jackson—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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