Southwest® flights from Charlotte to Chicago-Midway from $111

Promo Code

Low fares from Charlotte to Chicago-Midway

$

Charlotte (CLT)to

Chicago-Midway (MDW)
Depart: 12/21/2026

One-way

Basic

From
$111
Seen: 20 hrs ago

Charlotte (CLT)to

Chicago-Midway (MDW)
Depart: 01/13/2027

One-way

Basic

From
$111
Seen: 10 hrs ago

Charlotte (CLT)to

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

One-way

Basic

From
$111
Seen: 11 hrs ago

Charlotte (CLT)to

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

One-way

Basic

From
$111
Seen: 8 hrs ago

Charlotte (CLT)to

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

One-way

Basic

From
$111
Seen: 6 hrs ago

Charlotte (CLT)to

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

One-way

Basic

From
$111
Seen: 3 hrs ago

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Explore flights from Charlotte to Chicago-Midway

Oct 2026
From$245*
Seen: 7 hrs ago
One Way/Basic
Nov 2026
From$111*
Seen: 13 hrs ago
One Way/Basic
Dec 2026
From$111*
Seen: 16 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $111
cmp-daily-histogram-bars-legend-max-price-aria-label $309
Displaying fares for October-2026
  • CLT–MDW: cmp-view-offers-disclaimer. Find Offers
    22

    Thu

    OCT

  • CLT–MDW, 10/23/2026: From $294
    23

    Fri

  • CLT–MDW, 10/24/2026: From $245
    24

    Sat

  • CLT–MDW: cmp-view-offers-disclaimer. Find Offers
    25

    Sun

  • CLT–MDW, 10/26/2026: From $294
    26

    Mon

  • CLT–MDW, 10/27/2026: From $245
    27

    Tue

  • CLT–MDW, 10/28/2026: From $245
    28

    Wed

  • CLT–MDW, 10/29/2026: From $294
    29

    Thu

  • CLT–MDW, 10/30/2026: From $294
    30

    Fri

  • CLT–MDW, 10/31/2026: From $245
    31

    Sat

  • CLT–MDW, 11/01/2026: From $304
    01

    Sun

    NOV

  • CLT–MDW, 11/02/2026: From $309
    02

    Mon

  • CLT–MDW, 11/03/2026: From $245
    03

    Tue

  • CLT–MDW, 11/04/2026: From $245
    04

    Wed

  • CLT–MDW: cmp-view-offers-disclaimer. Find Offers
    05

    Thu

  • CLT–MDW, 11/06/2026: From $274
    06

    Fri

  • CLT–MDW, 11/07/2026: From $245
    07

    Sat

  • CLT–MDW, 11/08/2026: From $274
    08

    Sun

  • CLT–MDW, 11/09/2026: From $121
    09

    Mon

  • CLT–MDW, 11/10/2026: From $111
    10

    Tue

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

    Wed

  • CLT–MDW, 11/12/2026: From $114
    12

    Thu

  • CLT–MDW, 11/13/2026: From $114
    13

    Fri

  • CLT–MDW, 11/14/2026: From $111
    14

    Sat

  • CLT–MDW: cmp-view-offers-disclaimer. Find Offers
    15

    Sun

  • CLT–MDW, 11/16/2026: From $121
    16

    Mon

  • CLT–MDW, 11/17/2026: From $111
    17

    Tue

  • CLT–MDW: cmp-view-offers-disclaimer. Find Offers
    18

    Wed

  • CLT–MDW, 11/19/2026: From $111
    19

    Thu

  • CLT–MDW, 11/20/2026: From $114
    20

    Fri

  • CLT–MDW, 11/21/2026: From $111
    21

    Sat

    • Range$111-$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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