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

Promo Code

Low fares from Charlotte to Chicago-Midway

$

Charlotte (CLT)to

Chicago-Midway (MDW)
Depart: 12/02/2026

One-way

Basic

From
$129
Seen: 20 hrs ago

Charlotte (CLT)to

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

One-way

Basic

From
$129
Seen: 22 hrs ago

Charlotte (CLT)to

Chicago-Midway (MDW)
Depart: 10/22/2026

One-way

Basic

From
$129
Seen: 22 hrs ago

Charlotte (CLT)to

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

One-way

Basic

From
$129
Seen: 20 hrs ago

Charlotte (CLT)to

Chicago-Midway (MDW)
Depart: 11/10/2026

One-way

Basic

From
$129
Seen: 20 hrs ago

Charlotte (CLT)to

Chicago-Midway (MDW)
Depart: 12/10/2026

One-way

Basic

From
$129
Seen: 18 hrs ago

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Explore flights from Charlotte to Chicago-Midway

Sep 2026
From$235*
Seen: 13 hrs ago
One Way/Basic
Oct 2026
From$129*
Seen: 19 hrs ago
One Way/Basic
Nov 2026
From$129*
Seen: 19 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $177
cmp-daily-histogram-bars-legend-max-price-aria-label $299
Displaying fares for September-2026
  • CLT–MDW, 09/12/2026: From $235
    12

    Sat

    SEP

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

    Sun

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

    Mon

  • CLT–MDW, 09/15/2026: From $245
    15

    Tue

  • CLT–MDW, 09/16/2026: From $245
    16

    Wed

  • CLT–MDW, 09/17/2026: From $299
    17

    Thu

  • CLT–MDW, 09/18/2026: From $264
    18

    Fri

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

    Sat

  • CLT–MDW, 09/20/2026: From $264
    20

    Sun

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

    Mon

  • CLT–MDW, 09/22/2026: From $235
    22

    Tue

  • CLT–MDW, 09/23/2026: From $235
    23

    Wed

  • CLT–MDW, 09/24/2026: From $264
    24

    Thu

  • CLT–MDW, 09/25/2026: From $254
    25

    Fri

  • CLT–MDW, 09/26/2026: From $235
    26

    Sat

  • CLT–MDW, 09/27/2026: From $254
    27

    Sun

  • CLT–MDW, 09/28/2026: From $254
    28

    Mon

  • CLT–MDW, 09/29/2026: From $235
    29

    Tue

  • CLT–MDW, 09/30/2026: From $235
    30

    Wed

  • CLT–MDW, 10/01/2026: From $254
    01

    Thu

    OCT

  • CLT–MDW, 10/02/2026: From $177
    02

    Fri

  • CLT–MDW, 10/03/2026: From $177
    03

    Sat

  • CLT–MDW, 10/04/2026: From $243
    04

    Sun

  • CLT–MDW, 10/05/2026: From $177
    05

    Mon

  • CLT–MDW, 10/06/2026: From $177
    06

    Tue

  • CLT–MDW, 10/07/2026: From $177
    07

    Wed

  • CLT–MDW, 10/08/2026: From $177
    08

    Thu

  • CLT–MDW, 10/09/2026: From $187
    09

    Fri

  • CLT–MDW, 10/10/2026: From $177
    10

    Sat

  • CLT–MDW, 10/11/2026: From $207
    11

    Sun

    • Range$177-$299

    *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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