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

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Low fares from Jackson to Chicago-Midway

$

Jackson (JAN)to

Chicago-Midway (MDW)
Depart: 12/22/2026

One-way

Basic

From
$172
Seen: 15 hrs ago

Jackson (JAN)to

Chicago-Midway (MDW)
Depart: 12/02/2026

One-way

Basic

From
$172
Seen: 11 hrs ago

Jackson (JAN)to

Chicago-Midway (MDW)
Depart: 01/16/2027

One-way

Basic

From
$172
Seen: 5 hrs ago

Jackson (JAN)to

Chicago-Midway (MDW)
Depart: 12/09/2026

One-way

Basic

From
$172
Seen: 13 hrs ago

Jackson (JAN)to

Chicago-Midway (MDW)
Depart: 12/16/2026

One-way

Basic

From
$177
Seen: 6 hrs ago

Jackson (JAN)to

Chicago-Midway (MDW)
Depart: 12/30/2026

One-way

Basic

From
$179
Seen: 9 hrs ago

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Explore flights from Jackson to Chicago-Midway

Nov 2026
From$236*
Seen: 47 minutes ago
One Way/Basic
Dec 2026
From$172*
Seen: 15 hrs ago
One Way/Basic
Jan 2027
From$172*
Seen: 5 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $172
cmp-daily-histogram-bars-legend-max-price-aria-label $596
Displaying fares for November-2026
  • JAN–MDW, 11/11/2026: From $297
    11

    Wed

    NOV

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

    Thu

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

    Fri

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

    Sat

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

    Sun

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

    Mon

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

    Tue

  • JAN–MDW, 11/18/2026: From $297
    18

    Wed

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

    Thu

  • JAN–MDW, 11/20/2026: From $364
    20

    Fri

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

    Sat

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

    Sun

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

    Mon

  • JAN–MDW, 11/24/2026: From $250
    24

    Tue

  • JAN–MDW, 11/25/2026: From $236
    25

    Wed

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

    Thu

  • JAN–MDW, 11/27/2026: From $305
    27

    Fri

  • JAN–MDW, 11/28/2026: From $428
    28

    Sat

  • JAN–MDW, 11/29/2026: From $596
    29

    Sun

  • JAN–MDW, 11/30/2026: From $285
    30

    Mon

  • JAN–MDW, 12/01/2026: From $207
    01

    Tue

    DEC

  • JAN–MDW, 12/02/2026: From $172
    02

    Wed

  • JAN–MDW, 12/03/2026: From $212
    03

    Thu

  • JAN–MDW, 12/04/2026: From $207
    04

    Fri

  • JAN–MDW, 12/05/2026: From $207
    05

    Sat

  • JAN–MDW, 12/06/2026: From $224
    06

    Sun

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

    Mon

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

    Tue

  • JAN–MDW, 12/09/2026: From $172
    09

    Wed

  • JAN–MDW, 12/10/2026: From $192
    10

    Thu

    • Range$172-$596

    *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:
    Jackson-Evers International Airport
    Arriving at:
    Chicago Midway International Airport
    Distance:
    666 miles

    Questions we hear the most

    There are 64 weekly flights from Jackson to Chicago (Midway) on Southwest Airlines.
    To find the lowest fares by day and time to fly Jackson to Chicago (Midway) with Southwest, check out our Low Fare Calendar.
    You can rent a car at Chicago Midway International Airport book yours with your flight.
    Yes! Flights from Jackson to Chicago (Midway)—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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