Southwest® flights from Chicago-Midway to Jackson from $172

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Low fares from Chicago-Midway to Jackson

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Chicago-Midway (MDW)to

Jackson (JAN)
Depart: 02/10/2027

One-way

Basic

From
$172
Seen: 19 hrs ago

Chicago-Midway (MDW)to

Jackson (JAN)
Depart: 12/05/2026

One-way

Basic

From
$172
Seen: 10 minutes ago

Chicago-Midway (MDW)to

Jackson (JAN)
Depart: 12/08/2026

One-way

Basic

From
$177
Seen: 8 hrs ago

Chicago-Midway (MDW)to

Jackson (JAN)
Depart: 01/11/2027

One-way

Basic

From
$192
Seen: 17 hrs ago

Chicago-Midway (MDW)to

Jackson (JAN)
Depart: 12/07/2026

One-way

Basic

From
$192
Seen: 14 hrs ago

Chicago-Midway (MDW)to

Jackson (JAN)
Depart: 01/28/2027

One-way

Basic

From
$192
Seen: 6 hrs ago

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Explore flights from Chicago-Midway to Jackson

Nov 2026
From$264*
Seen: 2 hrs ago
One Way/Basic
Dec 2026
From$172*
Seen: 10 minutes ago
One Way/Basic
Jan 2027
From$192*
Seen: 6 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $172
cmp-daily-histogram-bars-legend-max-price-aria-label $391
Displaying fares for November-2026
  • MDW–JAN: cmp-view-offers-disclaimer. Find Offers
    12

    Thu

    NOV

  • MDW–JAN, 11/13/2026: From $373
    13

    Fri

  • MDW–JAN, 11/14/2026: From $299
    14

    Sat

  • MDW–JAN, 11/15/2026: From $373
    15

    Sun

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

    Mon

  • MDW–JAN, 11/17/2026: From $297
    17

    Tue

  • MDW–JAN, 11/18/2026: From $302
    18

    Wed

  • MDW–JAN, 11/19/2026: From $359
    19

    Thu

  • MDW–JAN, 11/20/2026: From $359
    20

    Fri

  • MDW–JAN, 11/21/2026: From $299
    21

    Sat

  • MDW–JAN, 11/22/2026: From $359
    22

    Sun

  • MDW–JAN, 11/23/2026: From $359
    23

    Mon

  • MDW–JAN, 11/24/2026: From $302
    24

    Tue

  • MDW–JAN, 11/25/2026: From $326
    25

    Wed

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

    Thu

  • MDW–JAN, 11/27/2026: From $264
    27

    Fri

  • MDW–JAN, 11/28/2026: From $359
    28

    Sat

  • MDW–JAN, 11/29/2026: From $391
    29

    Sun

  • MDW–JAN: cmp-view-offers-disclaimer. Find Offers
    30

    Mon

  • MDW–JAN, 12/01/2026: From $210
    01

    Tue

    DEC

  • MDW–JAN: cmp-view-offers-disclaimer. Find Offers
    02

    Wed

  • MDW–JAN, 12/03/2026: From $207
    03

    Thu

  • MDW–JAN, 12/04/2026: From $224
    04

    Fri

  • MDW–JAN, 12/05/2026: From $172
    05

    Sat

  • MDW–JAN, 12/06/2026: From $246
    06

    Sun

  • MDW–JAN, 12/07/2026: From $192
    07

    Mon

  • MDW–JAN, 12/08/2026: From $177
    08

    Tue

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

    Wed

  • MDW–JAN, 12/10/2026: From $207
    10

    Thu

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

    Fri

    • Range$172-$391

    *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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