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

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Low fares from Charlotte to Chicago (O'Hare)

$

Charlotte (CLT)to

Chicago (Midway) (MDW)
Depart: 10/17/2026

One-way

Basic

From
$139
Seen: 23 hrs ago

Charlotte (CLT)to

Chicago (Midway) (MDW)
Depart: 10/15/2026

One-way

Basic

From
$139
Seen: 20 hrs ago

Charlotte (CLT)to

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

One-way

Basic

From
$139
Seen: 16 hrs ago

Charlotte (CLT)to

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

One-way

Basic

From
$139
Seen: 15 hrs ago

Charlotte (CLT)to

Chicago (Midway) (MDW)
Depart: 10/01/2026

One-way

Basic

From
$139
Seen: 9 hrs ago

Charlotte (CLT)to

Chicago (Midway) (MDW)
Depart: 10/21/2026

One-way

Basic

From
$139
Seen: 18 hrs ago

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Explore flights from Charlotte to Chicago (O'Hare)

Aug 2026
From$215*
Seen: 3 hrs ago
One Way/Basic
Sep 2026
From$139*
Seen: 3 hrs ago
One Way/Basic
Oct 2026
From$139*
Seen: 8 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $139
cmp-daily-histogram-bars-legend-max-price-aria-label $244
Displaying fares for August-2026
  • CLT–MDW, 08/24/2026: From $234
    24

    Mon

    AUG

  • CLT–MDW, 08/25/2026: From $215
    25

    Tue

  • CLT–MDW, 08/26/2026: From $225
    26

    Wed

  • CLT–MDW, 08/27/2026: From $244
    27

    Thu

  • CLT–MDW, 08/28/2026: From $234
    28

    Fri

  • CLT–MDW, 08/29/2026: From $215
    29

    Sat

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

    Sun

  • CLT–MDW, 08/31/2026: From $234
    31

    Mon

  • CLT–MDW, 09/01/2026: From $215
    01

    Tue

    SEP

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

    Wed

  • CLT–MDW, 09/03/2026: From $234
    03

    Thu

  • CLT–MDW, 09/04/2026: From $234
    04

    Fri

  • CLT–MDW, 09/05/2026: From $145
    05

    Sat

  • CLT–MDW, 09/06/2026: From $155
    06

    Sun

  • CLT–MDW, 09/07/2026: From $234
    07

    Mon

  • CLT–MDW, 09/08/2026: From $215
    08

    Tue

  • CLT–MDW, 09/09/2026: From $145
    09

    Wed

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

    Thu

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

    Fri

  • CLT–MDW, 09/12/2026: From $145
    12

    Sat

  • CLT–MDW, 09/13/2026: From $213
    13

    Sun

  • CLT–MDW: cmp-view-offers-disclaimer. Find Offers
    14

    Mon

  • CLT–MDW, 09/15/2026: From $149
    15

    Tue

  • CLT–MDW, 09/16/2026: From $149
    16

    Wed

  • CLT–MDW, 09/17/2026: From $188
    17

    Thu

  • CLT–MDW, 09/18/2026: From $153
    18

    Fri

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

    Sat

  • CLT–MDW, 09/20/2026: From $213
    20

    Sun

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

    Mon

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

    Tue

  • CLT–MDW, 09/23/2026: From $139
    23

    Wed

    • Range$139-$244

    *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:
    Douglas Airport
    Arriving at:
    O'Hare International Airport
    Distance:
    599 miles

    Route Information

    17† 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 17 weekly flights from Charlotte to Chicago (O'Hare) on Southwest Airlines.
    To find the lowest fares by day and time to fly Charlotte 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 Charlotte 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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