Southwest® flights from Charleston to Chicago-Midway from $121

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Low fares from Charleston to Chicago-Midway

$

Charleston (CHS)to

Chicago-Midway (MDW)
Depart: 12/24/2026

One-way

Basic

From
$121
Seen: 19 hrs ago

Charleston (CHS)to

Chicago-Midway (MDW)
Depart: 12/08/2026

One-way

Basic

From
$121
Seen: 14 hrs ago

Charleston (CHS)to

Chicago-Midway (MDW)
Depart: 11/17/2026

One-way

Basic

From
$121
Seen: 13 hrs ago

Charleston (CHS)to

Chicago-Midway (MDW)
Depart: 01/15/2027

One-way

Basic

From
$121
Seen: 17 hrs ago

Charleston (CHS)to

Chicago-Midway (MDW)
Depart: 11/10/2026

One-way

Basic

From
$121
Seen: 9 hrs ago

Charleston (CHS)to

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

One-way

Basic

From
$121
Seen: 3 hrs ago

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Explore flights from Charleston to Chicago-Midway

Oct 2026
From$246*
Seen: 9 hrs ago
One Way/Basic
Nov 2026
From$121*
Seen: 15 hrs ago
One Way/Basic
Dec 2026
From$121*
Seen: 3 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $121
cmp-daily-histogram-bars-legend-max-price-aria-label $294
Displaying fares for October-2026
  • CHS–MDW, 10/22/2026: From $284
    22

    Thu

    OCT

  • CHS–MDW, 10/23/2026: From $284
    23

    Fri

  • CHS–MDW: cmp-view-offers-disclaimer. Find Offers
    24

    Sat

  • CHS–MDW: cmp-view-offers-disclaimer. Find Offers
    25

    Sun

  • CHS–MDW, 10/26/2026: From $284
    26

    Mon

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

    Tue

  • CHS–MDW, 10/28/2026: From $246
    28

    Wed

  • CHS–MDW, 10/29/2026: From $284
    29

    Thu

  • CHS–MDW, 10/30/2026: From $284
    30

    Fri

  • CHS–MDW: cmp-view-offers-disclaimer. Find Offers
    31

    Sat

  • CHS–MDW, 11/01/2026: From $294
    01

    Sun

    NOV

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

    Mon

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

    Tue

  • CHS–MDW, 11/04/2026: From $246
    04

    Wed

  • CHS–MDW: cmp-view-offers-disclaimer. Find Offers
    05

    Thu

  • CHS–MDW, 11/06/2026: From $270
    06

    Fri

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    07

    Sat

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

    Sun

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    09

    Mon

  • CHS–MDW, 11/10/2026: From $121
    10

    Tue

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

    Wed

  • CHS–MDW, 11/12/2026: From $121
    12

    Thu

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

    Fri

  • CHS–MDW, 11/14/2026: From $142
    14

    Sat

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

    Sun

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

    Mon

  • CHS–MDW, 11/17/2026: From $121
    17

    Tue

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

    Wed

  • CHS–MDW, 11/19/2026: From $121
    19

    Thu

  • CHS–MDW, 11/20/2026: From $187
    20

    Fri

  • CHS–MDW, 11/21/2026: From $121
    21

    Sat

    • Range$121-$294

    *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:
    Charleston International Airport
    Arriving at:
    Chicago Midway International Airport
    Average flight time:
    2 hours 9 minutes
    Distance:
    745 miles

    Questions we hear the most

    The average flight time from Charleston to Chicago (Midway) is 2 hours 9 minutes.
    There are 133 weekly flights from Charleston to Chicago (Midway) on Southwest Airlines.
    Yes, Southwest flies nonstop from Charleston to Chicago (Midway) once per day from Monday through Friday.
    Yes, Southwest flies nonstop from Charleston to Chicago (Midway) once per day on Saturdays and 2 times per day on Sundays.
    To find the lowest fares by day and time to fly Charleston 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 Charleston 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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