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: 09/05/2026

One-way

Basic

From
$119
Seen: 18 hrs ago

Charleston (CHS)to

Chicago (Midway) (MDW)
Depart: 10/30/2026

One-way

Basic

From
$119
Seen: 15 hrs ago

Charleston (CHS)to

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

One-way

Basic

From
$119
Seen: 18 hrs ago

Charleston (CHS)to

Chicago (Midway) (MDW)
Depart: 09/06/2026

One-way

Basic

From
$119
Seen: 1 hour ago

Charleston (CHS)to

Chicago (Midway) (MDW)
Depart: 09/12/2026

One-way

Basic

From
$140
Seen: 18 hrs ago

Charleston (CHS)to

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

One-way

Basic

From
$140
Seen: 22 hrs ago

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Explore flights from Charleston to Chicago (O'Hare)

Aug 2026
From$140*
Seen: 15 hrs ago
One Way/Basic
Sep 2026
From$119*
Seen: 18 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 $140
cmp-daily-histogram-bars-legend-max-price-aria-label $293
Displaying fares for August-2026
  • CHS–MDW, 08/05/2026: From $216
    05

    Wed

    AUG

  • CHS–MDW, 08/06/2026: From $271
    06

    Thu

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

    Fri

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

    Sat

  • CHS–MDW, 08/09/2026: From $293
    09

    Sun

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

    Mon

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

    Tue

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

    Wed

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

    Thu

  • CHS–MDW, 08/14/2026: From $271
    14

    Fri

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

    Sat

  • CHS–MDW, 08/16/2026: From $281
    16

    Sun

  • CHS–MDW, 08/17/2026: From $271
    17

    Mon

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

    Tue

  • CHS–MDW: cmp-view-offers-disclaimer. Find Offers
    19

    Wed

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

    Thu

  • CHS–MDW, 08/21/2026: From $240
    21

    Fri

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    22

    Sat

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

    Sun

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

    Mon

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

    Tue

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

    Wed

  • CHS–MDW, 08/27/2026: From $140
    27

    Thu

  • CHS–MDW, 08/28/2026: From $170
    28

    Fri

  • CHS–MDW, 08/29/2026: From $140
    29

    Sat

  • CHS–MDW, 08/30/2026: From $242
    30

    Sun

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

    Mon

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

    Tue

    SEP

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    02

    Wed

  • CHS–MDW, 09/03/2026: From $140
    03

    Thu

  • CHS–MDW, 09/04/2026: From $170
    04

    Fri

    • Range$140-$293

    *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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