Southwest® flights from Charleston to Chicago-Midway from $149

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Low fares from Charleston to Chicago-Midway

$

Charleston (CHS)to

Chicago-Midway (MDW)
Depart: 10/29/2026

One-way

Basic

From
$149
Seen: 18 hrs ago

Charleston (CHS)to

Chicago-Midway (MDW)
Depart: 11/19/2026

One-way

Basic

From
$149
Seen: 15 hrs ago

Charleston (CHS)to

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

One-way

Basic

From
$149
Seen: 20 hrs ago

Charleston (CHS)to

Chicago-Midway (MDW)
Depart: 11/26/2026

One-way

Basic

From
$149
Seen: 16 hrs ago

Charleston (CHS)to

Chicago-Midway (MDW)
Depart: 12/14/2026

One-way

Basic

From
$149
Seen: 16 hrs ago

Charleston (CHS)to

Chicago-Midway (MDW)
Depart: 11/09/2026

One-way

Basic

From
$149
Seen: 13 hrs ago

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Explore flights from Charleston to Chicago-Midway

Oct 2026
From$149*
Seen: 18 hrs ago
One Way/Basic
Nov 2026
From$149*
Seen: 16 hrs ago
One Way/Basic
Dec 2026
From$149*
Seen: 13 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $149
cmp-daily-histogram-bars-legend-max-price-aria-label $306
Displaying fares for October-2026
  • CHS–MDW, 10/01/2026: From $274
    01

    Thu

    OCT

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

    Fri

  • CHS–MDW, 10/03/2026: From $236
    03

    Sat

  • CHS–MDW, 10/04/2026: From $284
    04

    Sun

  • CHS–MDW, 10/05/2026: From $274
    05

    Mon

  • CHS–MDW, 10/06/2026: From $273
    06

    Tue

  • CHS–MDW, 10/07/2026: From $236
    07

    Wed

  • CHS–MDW, 10/08/2026: From $274
    08

    Thu

  • CHS–MDW, 10/09/2026: From $274
    09

    Fri

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

    Sat

  • CHS–MDW, 10/11/2026: From $306
    11

    Sun

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    12

    Mon

  • CHS–MDW, 10/13/2026: From $236
    13

    Tue

  • CHS–MDW, 10/14/2026: From $270
    14

    Wed

  • CHS–MDW, 10/15/2026: From $260
    15

    Thu

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

    Fri

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

    Sat

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

    Sun

  • CHS–MDW, 10/19/2026: From $260
    19

    Mon

  • CHS–MDW, 10/20/2026: From $236
    20

    Tue

  • CHS–MDW, 10/21/2026: From $149
    21

    Wed

  • CHS–MDW: cmp-view-offers-disclaimer. Find Offers
    22

    Thu

  • CHS–MDW, 10/23/2026: From $160
    23

    Fri

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    24

    Sat

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

    Sun

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

    Mon

  • CHS–MDW, 10/27/2026: From $149
    27

    Tue

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

    Wed

  • CHS–MDW, 10/29/2026: From $149
    29

    Thu

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

    Fri

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

    Sat

    • Range$149-$306

    *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

    Route Information

    133† 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 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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