Southwest® flights from Chicago (Midway) to Charleston from $119

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Low fares from Chicago (Midway) to Charleston

$

Chicago (Midway) (MDW)to

Charleston (CHS)
Depart: 09/28/2026

One-way

Basic

From
$119
Seen: 22 hrs ago

Chicago (Midway) (MDW)to

Charleston (CHS)
Depart: 09/15/2026

One-way

Basic

From
$119
Seen: 22 hrs ago

Chicago (Midway) (MDW)to

Charleston (CHS)
Depart: 09/12/2026

One-way

Basic

From
$119
Seen: 9 hrs ago

Chicago (Midway) (MDW)to

Charleston (CHS)
Depart: 09/16/2026

One-way

Basic

From
$119
Seen: 10 hrs ago

Chicago (Midway) (MDW)to

Charleston (CHS)
Depart: 10/06/2026

One-way

Basic

From
$119
Seen: 12 hrs ago

Chicago (Midway) (MDW)to

Charleston (CHS)
Depart: 10/17/2026

One-way

Basic

From
$119
Seen: 9 hrs ago

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Explore flights from Chicago (Midway) to Charleston

Aug 2026
From$216*
Seen: 14 hrs ago
One Way/Basic
Sep 2026
From$119*
Seen: 7 hrs ago
One Way/Basic
Oct 2026
From$119*
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 $281
Displaying fares for August-2026
  • MDW–CHS, 08/22/2026: From $216
    22

    Sat

    AUG

  • MDW–CHS: cmp-view-offers-disclaimer. Find Offers
    23

    Sun

  • MDW–CHS, 08/24/2026: From $271
    24

    Mon

  • MDW–CHS, 08/25/2026: From $216
    25

    Tue

  • MDW–CHS, 08/26/2026: From $216
    26

    Wed

  • MDW–CHS, 08/27/2026: From $271
    27

    Thu

  • MDW–CHS, 08/28/2026: From $281
    28

    Fri

  • MDW–CHS, 08/29/2026: From $216
    29

    Sat

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

    Sun

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

    Mon

  • MDW–CHS: cmp-view-offers-disclaimer. Find Offers
    01

    Tue

    SEP

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

    Wed

  • MDW–CHS, 09/03/2026: From $240
    03

    Thu

  • MDW–CHS, 09/04/2026: From $240
    04

    Fri

  • MDW–CHS, 09/05/2026: From $176
    05

    Sat

  • MDW–CHS: cmp-view-offers-disclaimer. Find Offers
    06

    Sun

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

    Mon

  • MDW–CHS, 09/08/2026: From $216
    08

    Tue

  • MDW–CHS, 09/09/2026: From $166
    09

    Wed

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

    Thu

  • MDW–CHS, 09/11/2026: From $140
    11

    Fri

  • MDW–CHS, 09/12/2026: From $119
    12

    Sat

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

    Sun

  • MDW–CHS, 09/14/2026: From $119
    14

    Mon

  • MDW–CHS, 09/15/2026: From $119
    15

    Tue

  • MDW–CHS, 09/16/2026: From $119
    16

    Wed

  • MDW–CHS, 09/17/2026: From $140
    17

    Thu

  • MDW–CHS, 09/18/2026: From $140
    18

    Fri

  • MDW–CHS: cmp-view-offers-disclaimer. Find Offers
    19

    Sat

  • MDW–CHS, 09/20/2026: From $200
    20

    Sun

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

    Mon

    • Range$119-$281

    *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:
    Charleston International Airport
    Average flight time:
    2 hours
    Distance:
    745 miles

    Route Information

    122† Weekly flights
    • 1‡ Nonstop flight per day Monday through Friday
    • 1‡ Nonstop flight on Saturday
    • 2‡ Nonstop flights on Sunday

    † Weekly flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025. Note: route may not operate every day of the week.

    ‡ Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025.

    Questions we hear the most

    The average flight time from Chicago (Midway) to Charleston is 2 hours.
    There are 122 weekly flights from Chicago (Midway) to Charleston on Southwest Airlines.
    Yes, Southwest flies nonstop from Chicago (Midway) to Charleston once per day from Monday through Friday.
    Yes, Southwest flies nonstop from Chicago (Midway) to Charleston once per day on Saturdays and 2 times per day on Sundays.
    To find the lowest fares by day and time to fly Chicago (Midway) to Charleston with Southwest, check out our Low Fare Calendar.
    You can rent a car at Charleston International Airport book yours with your flight.
    Yes! Flights from Chicago (Midway) to Charleston—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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