Southwest® flights from Charleston to Chicago-Midway from $185

Promo Code

Low fares from Charleston to Chicago-Midway

$

Charleston (CHS)to

Chicago-Midway (MDW)
Depart: 12/15/2026

One-way

Basic

From
$185
Seen: 9 hrs ago

Charleston (CHS)to

Chicago-Midway (MDW)
Depart: 12/30/2026

One-way

Basic

From
$185
Seen: 8 hrs ago

Charleston (CHS)to

Chicago-Midway (MDW)
Depart: 12/29/2026

One-way

Basic

From
$185
Seen: 1 hour ago

Charleston (CHS)to

Chicago-Midway (MDW)
Depart: 12/16/2026

One-way

Basic

From
$185
Seen: 2 hrs ago

Charleston (CHS)to

Chicago-Midway (MDW)
Depart: 12/01/2026

One-way

Basic

From
$185
Seen: 14 hrs ago

Charleston (CHS)to

Chicago-Midway (MDW)
Depart: 12/02/2026

One-way

Basic

From
$185
Seen: 13 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 Charleston to Chicago-Midway

Nov 2026
From$223*
Seen: 14 hrs ago
One Way/Basic
Dec 2026
From$185*
Seen: 2 hrs ago
One Way/Basic
Jan 2027
From$195*
Seen: 17 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $185
cmp-daily-histogram-bars-legend-max-price-aria-label $581
Displaying fares for November-2026
  • CHS–MDW, 11/11/2026: From $233
    11

    Wed

    NOV

  • CHS–MDW, 11/12/2026: From $223
    12

    Thu

  • CHS–MDW, 11/13/2026: From $223
    13

    Fri

  • CHS–MDW, 11/14/2026: From $233
    14

    Sat

  • CHS–MDW, 11/15/2026: From $256
    15

    Sun

  • CHS–MDW, 11/16/2026: From $233
    16

    Mon

  • CHS–MDW, 11/17/2026: From $223
    17

    Tue

  • CHS–MDW, 11/18/2026: From $223
    18

    Wed

  • CHS–MDW, 11/19/2026: From $223
    19

    Thu

  • CHS–MDW, 11/20/2026: From $223
    20

    Fri

  • CHS–MDW, 11/21/2026: From $223
    21

    Sat

  • CHS–MDW, 11/22/2026: From $223
    22

    Sun

  • CHS–MDW, 11/23/2026: From $223
    23

    Mon

  • CHS–MDW, 11/24/2026: From $233
    24

    Tue

  • CHS–MDW, 11/25/2026: From $233
    25

    Wed

  • CHS–MDW, 11/26/2026: From $223
    26

    Thu

  • CHS–MDW, 11/27/2026: From $251
    27

    Fri

  • CHS–MDW, 11/28/2026: From $581
    28

    Sat

  • CHS–MDW, 11/29/2026: From $339
    29

    Sun

  • CHS–MDW, 11/30/2026: From $233
    30

    Mon

  • CHS–MDW, 12/01/2026: From $185
    01

    Tue

    DEC

  • CHS–MDW, 12/02/2026: From $185
    02

    Wed

  • CHS–MDW, 12/03/2026: From $205
    03

    Thu

  • CHS–MDW, 12/04/2026: From $220
    04

    Fri

  • CHS–MDW, 12/05/2026: From $195
    05

    Sat

  • CHS–MDW, 12/06/2026: From $223
    06

    Sun

  • CHS–MDW, 12/07/2026: From $205
    07

    Mon

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

    Tue

  • CHS–MDW: cmp-view-offers-disclaimer. Find Offers
    09

    Wed

  • CHS–MDW, 12/10/2026: From $205
    10

    Thu

    • Range$185-$581

    *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.

    Explore Flights from Other Popular Origins

    Popular Flights from Charleston