Southwest® flights from Chicago-Midway to Charleston from $132

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Low fares from Chicago-Midway to Charleston

$

Chicago-Midway (MDW)to

Charleston (CHS)
Depart: 11/02/2026

One-way

Basic

From
$132
Seen: 5 hrs ago

Chicago-Midway (MDW)to

Charleston (CHS)
Depart: 11/03/2026

One-way

Basic

From
$161
Seen: 7 hrs ago

Chicago-Midway (MDW)to

Charleston (CHS)
Depart: 11/17/2026

One-way

Basic

From
$161
Seen: 23 hrs ago

Chicago-Midway (MDW)to

Charleston (CHS)
Depart: 10/26/2026

One-way

Basic

From
$161
Seen: 22 hrs ago

Chicago-Midway (MDW)to

Charleston (CHS)
Depart: 10/20/2026

One-way

Basic

From
$161
Seen: 7 hrs ago

Chicago-Midway (MDW)to

Charleston (CHS)
Depart: 10/31/2026

One-way

Basic

From
$161
Seen: 4 hrs ago

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Explore flights from Chicago-Midway to Charleston

Sep 2026
From$226*
Seen: 17 hrs ago
One Way/Basic
Oct 2026
From$161*
Seen: 22 hrs ago
One Way/Basic
Nov 2026
From$132*
Seen: 5 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $194
cmp-daily-histogram-bars-legend-max-price-aria-label $318
Displaying fares for September-2026
  • MDW–CHS: cmp-view-offers-disclaimer. Find Offers
    11

    Fri

    SEP

  • MDW–CHS, 09/12/2026: From $236
    12

    Sat

  • MDW–CHS, 09/13/2026: From $302
    13

    Sun

  • MDW–CHS, 09/14/2026: From $264
    14

    Mon

  • MDW–CHS, 09/15/2026: From $226
    15

    Tue

  • MDW–CHS, 09/16/2026: From $226
    16

    Wed

  • MDW–CHS, 09/17/2026: From $264
    17

    Thu

  • MDW–CHS, 09/18/2026: From $264
    18

    Fri

  • MDW–CHS, 09/19/2026: From $236
    19

    Sat

  • MDW–CHS, 09/20/2026: From $264
    20

    Sun

  • MDW–CHS, 09/21/2026: From $274
    21

    Mon

  • MDW–CHS, 09/22/2026: From $226
    22

    Tue

  • MDW–CHS, 09/23/2026: From $236
    23

    Wed

  • MDW–CHS, 09/24/2026: From $250
    24

    Thu

  • MDW–CHS, 09/25/2026: From $250
    25

    Fri

  • MDW–CHS, 09/26/2026: From $226
    26

    Sat

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

    Sun

  • MDW–CHS, 09/28/2026: From $250
    28

    Mon

  • MDW–CHS, 09/29/2026: From $226
    29

    Tue

  • MDW–CHS, 09/30/2026: From $226
    30

    Wed

  • MDW–CHS, 10/01/2026: From $209
    01

    Thu

    OCT

  • MDW–CHS, 10/02/2026: From $199
    02

    Fri

  • MDW–CHS, 10/03/2026: From $194
    03

    Sat

  • MDW–CHS, 10/04/2026: From $220
    04

    Sun

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

    Mon

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

    Tue

  • MDW–CHS, 10/07/2026: From $204
    07

    Wed

  • MDW–CHS, 10/08/2026: From $318
    08

    Thu

  • MDW–CHS, 10/09/2026: From $220
    09

    Fri

  • MDW–CHS, 10/10/2026: From $209
    10

    Sat

    • Range$194-$318

    *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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