Southwest® flights from Charleston to Chicago (O'Hare)

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Low fares from Charleston to Chicago (O'Hare)

$

Charleston (CHS)to

Chicago (Midway) (MDW)
Depart: 10/03/2026

One-way

Basic

From
$119
Seen: 12 hrs ago

Charleston (CHS)to

Chicago (Midway) (MDW)
Depart: 11/05/2026

One-way

Basic

From
$119
Seen: 13 hrs ago

Charleston (CHS)to

Chicago (Midway) (MDW)
Depart: 09/26/2026

One-way

Basic

From
$119
Seen: 20 hrs ago

Charleston (CHS)to

Chicago (Midway) (MDW)
Depart: 10/27/2026

One-way

Basic

From
$119
Seen: 46 minutes ago

Charleston (CHS)to

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

One-way

Basic

From
$119
Seen: 19 hrs ago

Charleston (CHS)to

Chicago (Midway) (MDW)
Depart: 09/14/2026

One-way

Basic

From
$119
Seen: 16 hrs ago

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Explore flights from Charleston to Chicago (O'Hare)

Aug 2026
From$216*
Seen: 17 hrs ago
One Way/Basic
Sep 2026
From$119*
Seen: 13 hrs ago
One Way/Basic
Oct 2026
From$119*
Seen: 15 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $119
cmp-daily-histogram-bars-legend-max-price-aria-label $286
Displaying fares for August-2026
  • CHS–MDW, 08/25/2026: From $216
    25

    Tue

    AUG

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

    Wed

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

    Thu

  • CHS–MDW, 08/28/2026: From $271
    28

    Fri

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

    Sat

  • CHS–MDW, 08/30/2026: From $271
    30

    Sun

  • CHS–MDW, 08/31/2026: From $271
    31

    Mon

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

    Tue

    SEP

  • CHS–MDW, 09/02/2026: From $216
    02

    Wed

  • CHS–MDW, 09/03/2026: From $271
    03

    Thu

  • CHS–MDW, 09/04/2026: From $271
    04

    Fri

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

    Sat

  • CHS–MDW, 09/06/2026: From $271
    06

    Sun

  • CHS–MDW, 09/07/2026: From $286
    07

    Mon

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

    Tue

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

    Wed

  • CHS–MDW, 09/10/2026: From $166
    10

    Thu

  • CHS–MDW: cmp-view-offers-disclaimer. Find Offers
    11

    Fri

  • CHS–MDW, 09/12/2026: From $166
    12

    Sat

  • CHS–MDW, 09/13/2026: From $250
    13

    Sun

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

    Mon

  • CHS–MDW: cmp-view-offers-disclaimer. Find Offers
    15

    Tue

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

    Wed

  • CHS–MDW, 09/17/2026: From $119
    17

    Thu

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

    Fri

  • CHS–MDW, 09/19/2026: From $119
    19

    Sat

  • CHS–MDW: cmp-view-offers-disclaimer. Find Offers
    20

    Sun

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

    Mon

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

    Tue

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

    Wed

  • CHS–MDW, 09/24/2026: From $119
    24

    Thu

    • Range$119-$286

    *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:
    O'Hare International Airport
    Distance:
    760 miles

    Route Information

    52† Weekly flights

    † 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

    There are 52 weekly flights from Charleston to Chicago (O'Hare) on Southwest Airlines.
    To find the lowest fares by day and time to fly Charleston to Chicago (O'Hare) with Southwest, check out our Low Fare Calendar.
    You can rent a car at O'Hare International Airport book yours with your flight.
    Yes! Flights from Charleston to Chicago (O'Hare)—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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