Southwest® flights from Charlotte to Chicago (Midway) from $130

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Low fares from Charlotte to Chicago (Midway)

$

Charlotte (CLT)to

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

One-way

Basic

From
$130
Seen: 9 hrs ago

Charlotte (CLT)to

Chicago (Midway) (MDW)
Depart: 09/05/2026

One-way

Basic

From
$130
Seen: 13 hrs ago

Charlotte (CLT)to

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

One-way

Basic

From
$140
Seen: 6 hrs ago

Charlotte (CLT)to

Chicago (Midway) (MDW)
Depart: 09/24/2026

One-way

Basic

From
$142
Seen: 8 hrs ago

Charlotte (CLT)to

Chicago (Midway) (MDW)
Depart: 08/22/2026

One-way

Basic

From
$142
Seen: 5 hrs ago

Charlotte (CLT)to

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

One-way

Basic

From
$142
Seen: 5 hrs ago

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Explore flights from Charlotte to Chicago (Midway)

Aug 2026
From$142*
Seen: 5 hrs ago
One Way/Basic
Sep 2026
From$130*
Seen: 9 hrs ago
One Way/Basic
Oct 2026
From$142*
Seen: 13 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $142
cmp-daily-histogram-bars-legend-max-price-aria-label $274
Displaying fares for August-2026
  • CLT–MDW, 08/02/2026: From $264
    02

    Sun

    AUG

  • CLT–MDW, 08/03/2026: From $264
    03

    Mon

  • CLT–MDW, 08/04/2026: From $215
    04

    Tue

  • CLT–MDW, 08/05/2026: From $215
    05

    Wed

  • CLT–MDW, 08/06/2026: From $274
    06

    Thu

  • CLT–MDW, 08/07/2026: From $264
    07

    Fri

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

    Sat

  • CLT–MDW, 08/09/2026: From $264
    09

    Sun

  • CLT–MDW, 08/10/2026: From $264
    10

    Mon

  • CLT–MDW, 08/11/2026: From $215
    11

    Tue

  • CLT–MDW, 08/12/2026: From $225
    12

    Wed

  • CLT–MDW, 08/13/2026: From $274
    13

    Thu

  • CLT–MDW, 08/14/2026: From $234
    14

    Fri

  • CLT–MDW, 08/15/2026: From $215
    15

    Sat

  • CLT–MDW, 08/16/2026: From $234
    16

    Sun

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

    Mon

  • CLT–MDW, 08/18/2026: From $215
    18

    Tue

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

    Wed

  • CLT–MDW, 08/20/2026: From $234
    20

    Thu

  • CLT–MDW, 08/21/2026: From $234
    21

    Fri

  • CLT–MDW, 08/22/2026: From $142
    22

    Sat

  • CLT–MDW, 08/23/2026: From $213
    23

    Sun

  • CLT–MDW, 08/24/2026: From $142
    24

    Mon

  • CLT–MDW, 08/25/2026: From $142
    25

    Tue

  • CLT–MDW, 08/26/2026: From $142
    26

    Wed

  • CLT–MDW, 08/27/2026: From $142
    27

    Thu

  • CLT–MDW, 08/28/2026: From $172
    28

    Fri

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

    Sat

  • CLT–MDW, 08/30/2026: From $187
    30

    Sun

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

    Mon

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

    Tue

    SEP

    • Range$142-$274

    *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:
    Chicago Midway International Airport
    Average flight time:
    2 hours
    Distance:
    584 miles

    Route Information

    110† Weekly flights
    • 2‡ Nonstop flights per day Monday through Friday
    • 1‡ Nonstop flight on Saturday
    • 3‡ 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 Charlotte to Chicago (Midway) is 2 hours.
    There are 110 weekly flights from Charlotte to Chicago (Midway) on Southwest Airlines.
    Yes, Southwest flies nonstop from Charlotte to Chicago (Midway) 2 times per day from Monday through Friday.
    Yes, Southwest flies nonstop from Charlotte to Chicago (Midway) once per day on Saturdays and 3 times per day on Sundays.
    To find the lowest fares by day and time to fly Charlotte 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 Charlotte 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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