Southwest® flights from Chicago (Midway) to Charleston from $140

Promo Code

Low fares from Chicago (Midway) to Charleston

$

Chicago (Midway) (MDW)to

Charleston (CHS)
Depart: 09/15/2026

One-way

Basic

From
$140
Seen: 8 hrs ago

Chicago (Midway) (MDW)to

Charleston (CHS)
Depart: 09/01/2026

One-way

Basic

From
$140
Seen: 10 hrs ago

Chicago (Midway) (MDW)to

Charleston (CHS)
Depart: 09/23/2026

One-way

Basic

From
$140
Seen: 9 hrs ago

Chicago (Midway) (MDW)to

Charleston (CHS)
Depart: 10/17/2026

One-way

Basic

From
$140
Seen: 21 hrs ago

Chicago (Midway) (MDW)to

Charleston (CHS)
Depart: 10/06/2026

One-way

Basic

From
$140
Seen: 17 hrs ago

Chicago (Midway) (MDW)to

Charleston (CHS)
Depart: 09/28/2026

One-way

Basic

From
$140
Seen: 6 hrs ago

Looking for more low-fare flights?

Check out the Low Fare Calendar to find a fare that works for you. Just choose the month you want to depart and return, and we’ll show you the best fares available.

Find low fares

Explore flights from Chicago (Midway) to Charleston

Aug 2026
From$140*
Seen: 7 hrs ago
One Way/Basic
Sep 2026
From$140*
Seen: 13 hrs ago
One Way/Basic
Oct 2026
From$140*
Seen: 21 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $140
cmp-daily-histogram-bars-legend-max-price-aria-label $271
Displaying fares for August-2026
  • MDW–CHS, 08/01/2026: From $263
    01

    Sat

    AUG

  • MDW–CHS, 08/02/2026: From $271
    02

    Sun

  • MDW–CHS, 08/03/2026: From $271
    03

    Mon

  • MDW–CHS, 08/04/2026: From $216
    04

    Tue

  • MDW–CHS, 08/05/2026: From $216
    05

    Wed

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

    Thu

  • MDW–CHS, 08/07/2026: From $271
    07

    Fri

  • MDW–CHS, 08/08/2026: From $231
    08

    Sat

  • MDW–CHS, 08/09/2026: From $271
    09

    Sun

  • MDW–CHS, 08/10/2026: From $271
    10

    Mon

  • MDW–CHS, 08/11/2026: From $216
    11

    Tue

  • MDW–CHS, 08/12/2026: From $216
    12

    Wed

  • MDW–CHS, 08/13/2026: From $271
    13

    Thu

  • MDW–CHS, 08/14/2026: From $240
    14

    Fri

  • MDW–CHS, 08/15/2026: From $216
    15

    Sat

  • MDW–CHS, 08/16/2026: From $240
    16

    Sun

  • MDW–CHS, 08/17/2026: From $240
    17

    Mon

  • MDW–CHS, 08/18/2026: From $216
    18

    Tue

  • MDW–CHS, 08/19/2026: From $216
    19

    Wed

  • MDW–CHS, 08/20/2026: From $240
    20

    Thu

  • MDW–CHS, 08/21/2026: From $170
    21

    Fri

  • MDW–CHS, 08/22/2026: From $140
    22

    Sat

  • MDW–CHS, 08/23/2026: From $210
    23

    Sun

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

    Mon

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

    Tue

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

    Wed

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

    Thu

  • MDW–CHS: cmp-view-offers-disclaimer. Find Offers
    28

    Fri

  • MDW–CHS: cmp-view-offers-disclaimer. Find Offers
    29

    Sat

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

    Sun

  • MDW–CHS, 08/31/2026: From $140
    31

    Mon

    • Range$140-$271

    *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.

    Explore Flights from Other Popular Origins

    Popular Flights from Chicago (Midway)