Southwest® flights from Chicago-Midway to Jackson from $114

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Low fares from Chicago-Midway to Jackson

$

Chicago-Midway (MDW)to

Jackson (JAN)
Depart: 12/15/2026

One-way

Basic

From
$114
Seen: 21 hrs ago

Chicago-Midway (MDW)to

Jackson (JAN)
Depart: 11/10/2026

One-way

Basic

From
$114
Seen: 22 hrs ago

Chicago-Midway (MDW)to

Jackson (JAN)
Depart: 12/05/2026

One-way

Basic

From
$114
Seen: 21 hrs ago

Chicago-Midway (MDW)to

Jackson (JAN)
Depart: 01/23/2027

One-way

Basic

From
$114
Seen: 6 hrs ago

Chicago-Midway (MDW)to

Jackson (JAN)
Depart: 12/09/2026

One-way

Basic

From
$114
Seen: 23 hrs ago

Chicago-Midway (MDW)to

Jackson (JAN)
Depart: 11/18/2026

One-way

Basic

From
$114
Seen: 46 minutes ago

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Explore flights from Chicago-Midway to Jackson

Oct 2026
From$294*
Seen: 9 hrs ago
One Way/Basic
Nov 2026
From$114*
Seen: 46 minutes ago
One Way/Basic
Dec 2026
From$114*
Seen: 23 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $114
cmp-daily-histogram-bars-legend-max-price-aria-label $517
Displaying fares for October-2026
  • MDW–JAN, 10/23/2026: From $407
    23

    Fri

    OCT

  • MDW–JAN, 10/24/2026: From $294
    24

    Sat

  • MDW–JAN, 10/25/2026: From $517
    25

    Sun

  • MDW–JAN: cmp-view-offers-disclaimer. Find Offers
    26

    Mon

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

    Tue

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

    Wed

  • MDW–JAN, 10/29/2026: From $354
    29

    Thu

  • MDW–JAN, 10/30/2026: From $354
    30

    Fri

  • MDW–JAN, 10/31/2026: From $294
    31

    Sat

  • MDW–JAN, 11/01/2026: From $354
    01

    Sun

    NOV

  • MDW–JAN, 11/02/2026: From $354
    02

    Mon

  • MDW–JAN, 11/03/2026: From $292
    03

    Tue

  • MDW–JAN, 11/04/2026: From $292
    04

    Wed

  • MDW–JAN, 11/05/2026: From $340
    05

    Thu

  • MDW–JAN, 11/06/2026: From $264
    06

    Fri

  • MDW–JAN, 11/07/2026: From $185
    07

    Sat

  • MDW–JAN: cmp-view-offers-disclaimer. Find Offers
    08

    Sun

  • MDW–JAN, 11/09/2026: From $259
    09

    Mon

  • MDW–JAN, 11/10/2026: From $114
    10

    Tue

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

    Wed

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

    Thu

  • MDW–JAN, 11/13/2026: From $205
    13

    Fri

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

    Sat

  • MDW–JAN, 11/15/2026: From $215
    15

    Sun

  • MDW–JAN, 11/16/2026: From $141
    16

    Mon

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

    Tue

  • MDW–JAN, 11/18/2026: From $114
    18

    Wed

  • MDW–JAN, 11/19/2026: From $134
    19

    Thu

  • MDW–JAN, 11/20/2026: From $241
    20

    Fri

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

    Sat

  • MDW–JAN: cmp-view-offers-disclaimer. Find Offers
    22

    Sun

    • Range$114-$517

    *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

    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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