Southwest® flights from Charlotte to Chicago-Midway from $129

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Low fares from Charlotte to Chicago-Midway

$

Charlotte (CLT)to

Chicago-Midway (MDW)
Depart: 11/17/2026

One-way

Basic

From
$129
Seen: 23 hrs ago

Charlotte (CLT)to

Chicago-Midway (MDW)
Depart: 11/16/2026

One-way

Basic

From
$129
Seen: 20 hrs ago

Charlotte (CLT)to

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

One-way

Basic

From
$129
Seen: 20 hrs ago

Charlotte (CLT)to

Chicago-Midway (MDW)
Depart: 11/21/2026

One-way

Basic

From
$129
Seen: 5 hrs ago

Charlotte (CLT)to

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

One-way

Basic

From
$129
Seen: 16 hrs ago

Charlotte (CLT)to

Chicago-Midway (MDW)
Depart: 10/28/2026

One-way

Basic

From
$129
Seen: 10 hrs ago

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Explore flights from Charlotte to Chicago-Midway

Oct 2026
From$129*
Seen: 5 hrs ago
One Way/Basic
Nov 2026
From$129*
Seen: 23 hrs ago
One Way/Basic
Dec 2026
From$129*
Seen: 19 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $129
cmp-daily-histogram-bars-legend-max-price-aria-label $369
Displaying fares for October-2026
  • CLT–MDW, 10/02/2026: From $274
    02

    Fri

    OCT

  • CLT–MDW, 10/03/2026: From $235
    03

    Sat

  • CLT–MDW, 10/04/2026: From $284
    04

    Sun

  • CLT–MDW, 10/05/2026: From $284
    05

    Mon

  • CLT–MDW, 10/06/2026: From $235
    06

    Tue

  • CLT–MDW, 10/07/2026: From $235
    07

    Wed

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

    Thu

  • CLT–MDW, 10/09/2026: From $369
    09

    Fri

  • CLT–MDW, 10/10/2026: From $274
    10

    Sat

  • CLT–MDW, 10/11/2026: From $274
    11

    Sun

  • CLT–MDW, 10/12/2026: From $274
    12

    Mon

  • CLT–MDW: cmp-view-offers-disclaimer. Find Offers
    13

    Tue

  • CLT–MDW, 10/14/2026: From $235
    14

    Wed

  • CLT–MDW, 10/15/2026: From $254
    15

    Thu

  • CLT–MDW, 10/16/2026: From $254
    16

    Fri

  • CLT–MDW, 10/17/2026: From $235
    17

    Sat

  • CLT–MDW, 10/18/2026: From $254
    18

    Sun

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

    Mon

  • CLT–MDW, 10/20/2026: From $235
    20

    Tue

  • CLT–MDW, 10/21/2026: From $235
    21

    Wed

  • CLT–MDW, 10/22/2026: From $179
    22

    Thu

  • CLT–MDW, 10/23/2026: From $139
    23

    Fri

  • CLT–MDW, 10/24/2026: From $129
    24

    Sat

  • CLT–MDW, 10/25/2026: From $243
    25

    Sun

  • CLT–MDW, 10/26/2026: From $189
    26

    Mon

  • CLT–MDW, 10/27/2026: From $129
    27

    Tue

  • CLT–MDW, 10/28/2026: From $129
    28

    Wed

  • CLT–MDW, 10/29/2026: From $139
    29

    Thu

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

    Fri

  • CLT–MDW, 10/31/2026: From $139
    31

    Sat

  • CLT–MDW, 11/01/2026: From $207
    01

    Sun

    NOV

    • Range$129-$369

    *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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