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

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Low fares from Jackson to Chicago-Midway

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Jackson (JAN)to

Chicago-Midway (MDW)
Depart: 01/19/2027

One-way

Basic

From
$114
Seen: 11 hrs ago

Jackson (JAN)to

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

One-way

Basic

From
$114
Seen: 20 hrs ago

Jackson (JAN)to

Chicago-Midway (MDW)
Depart: 12/23/2026

One-way

Basic

From
$114
Seen: 1 hour ago

Jackson (JAN)to

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

One-way

Basic

From
$114
Seen: 1 hour ago

Jackson (JAN)to

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

One-way

Basic

From
$114
Seen: 13 hrs ago

Jackson (JAN)to

Chicago-Midway (MDW)
Depart: 12/19/2026

One-way

Basic

From
$114
Seen: 4 hrs ago

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Explore flights from Jackson to Chicago-Midway

Oct 2026
From$292*
Seen: 8 hrs ago
One Way/Basic
Nov 2026
From$119*
Seen: 11 hrs ago
One Way/Basic
Dec 2026
From$114*
Seen: 4 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $119
cmp-daily-histogram-bars-legend-max-price-aria-label $368
Displaying fares for October-2026
  • JAN–MDW, 10/22/2026: From $368
    22

    Thu

    OCT

  • JAN–MDW, 10/23/2026: From $368
    23

    Fri

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

    Sat

  • JAN–MDW, 10/25/2026: From $368
    25

    Sun

  • JAN–MDW, 10/26/2026: From $368
    26

    Mon

  • JAN–MDW, 10/27/2026: From $292
    27

    Tue

  • JAN–MDW, 10/28/2026: From $292
    28

    Wed

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

    Thu

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

    Fri

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

    Sat

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

    Sun

    NOV

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

    Mon

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    03

    Tue

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    04

    Wed

  • JAN–MDW, 11/05/2026: From $259
    05

    Thu

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    06

    Fri

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    07

    Sat

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    08

    Sun

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

    Mon

  • JAN–MDW: cmp-view-offers-disclaimer. Find Offers
    10

    Tue

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

    Wed

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

    Thu

  • JAN–MDW: cmp-view-offers-disclaimer. Find Offers
    13

    Fri

  • JAN–MDW, 11/14/2026: From $119
    14

    Sat

  • JAN–MDW, 11/15/2026: From $145
    15

    Sun

  • JAN–MDW, 11/16/2026: From $134
    16

    Mon

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

    Tue

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

    Wed

  • JAN–MDW, 11/19/2026: From $147
    19

    Thu

  • JAN–MDW, 11/20/2026: From $219
    20

    Fri

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

    Sat

    • Range$119-$368

    *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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