Southwest® flights from Charlotte to Chicago-Midway from $145

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Low fares from Charlotte to Chicago-Midway

$

Charlotte (CLT)to

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

One-way

Basic

From
$145
Seen: 19 hrs ago

Charlotte (CLT)to

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

One-way

Basic

From
$145
Seen: 14 hrs ago

Charlotte (CLT)to

Chicago-Midway (MDW)
Depart: 01/16/2027

One-way

Basic

From
$145
Seen: 12 hrs ago

Charlotte (CLT)to

Chicago-Midway (MDW)
Depart: 12/15/2026

One-way

Basic

From
$145
Seen: 1 hour ago

Charlotte (CLT)to

Chicago-Midway (MDW)
Depart: 02/10/2027

One-way

Basic

From
$145
Seen: 15 hrs ago

Charlotte (CLT)to

Chicago-Midway (MDW)
Depart: 12/23/2026

One-way

Basic

From
$145
Seen: 14 hrs ago

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Explore flights from Charlotte to Chicago-Midway

Nov 2026
From$250*
Seen: 8 hrs ago
One Way/Basic
Dec 2026
From$145*
Seen: 14 hrs ago
One Way/Basic
Jan 2027
From$145*
Seen: 2 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $145
cmp-daily-histogram-bars-legend-max-price-aria-label $309
Displaying fares for November-2026
  • CLT–MDW, 11/11/2026: From $250
    11

    Wed

    NOV

  • CLT–MDW, 11/12/2026: From $269
    12

    Thu

  • CLT–MDW, 11/13/2026: From $269
    13

    Fri

  • CLT–MDW, 11/14/2026: From $250
    14

    Sat

  • CLT–MDW, 11/15/2026: From $309
    15

    Sun

  • CLT–MDW, 11/16/2026: From $269
    16

    Mon

  • CLT–MDW, 11/17/2026: From $250
    17

    Tue

  • CLT–MDW, 11/18/2026: From $250
    18

    Wed

  • CLT–MDW, 11/19/2026: From $269
    19

    Thu

  • CLT–MDW, 11/20/2026: From $269
    20

    Fri

  • CLT–MDW, 11/21/2026: From $250
    21

    Sat

  • CLT–MDW, 11/22/2026: From $269
    22

    Sun

  • CLT–MDW, 11/23/2026: From $269
    23

    Mon

  • CLT–MDW, 11/24/2026: From $250
    24

    Tue

  • CLT–MDW, 11/25/2026: From $250
    25

    Wed

  • CLT–MDW, 11/26/2026: From $269
    26

    Thu

  • CLT–MDW, 11/27/2026: From $269
    27

    Fri

  • CLT–MDW, 11/28/2026: From $280
    28

    Sat

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

    Sun

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

    Mon

  • CLT–MDW, 12/01/2026: From $145
    01

    Tue

    DEC

  • CLT–MDW, 12/02/2026: From $145
    02

    Wed

  • CLT–MDW, 12/03/2026: From $165
    03

    Thu

  • CLT–MDW, 12/04/2026: From $180
    04

    Fri

  • CLT–MDW, 12/05/2026: From $145
    05

    Sat

  • CLT–MDW: cmp-view-offers-disclaimer. Find Offers
    06

    Sun

  • CLT–MDW: cmp-view-offers-disclaimer. Find Offers
    07

    Mon

  • CLT–MDW, 12/08/2026: From $145
    08

    Tue

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

    Wed

  • CLT–MDW, 12/10/2026: From $165
    10

    Thu

    • Range$145-$309

    *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

    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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