Southwest® flights from Raleigh/Durham to Chicago-Midway from $125

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Low fares from Raleigh/Durham to Chicago-Midway

$

Raleigh/Durham (RDU)to

Chicago-Midway (MDW)
Depart: 01/05/2027

One-way

Basic

From
$125
Seen: 21 hrs ago

Raleigh/Durham (RDU)to

Chicago-Midway (MDW)
Depart: 01/09/2027

One-way

Basic

From
$125
Seen: 12 hrs ago

Raleigh/Durham (RDU)to

Chicago-Midway (MDW)
Depart: 12/05/2026

One-way

Basic

From
$125
Seen: 13 hrs ago

Raleigh/Durham (RDU)to

Chicago-Midway (MDW)
Depart: 12/22/2026

One-way

Basic

From
$125
Seen: 4 hrs ago

Raleigh/Durham (RDU)to

Chicago-Midway (MDW)
Depart: 12/29/2026

One-way

Basic

From
$125
Seen: 2 hrs ago

Raleigh/Durham (RDU)to

Chicago-Midway (MDW)
Depart: 02/16/2027

One-way

Basic

From
$125
Seen: 13 hrs ago

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Explore flights from Raleigh/Durham to Chicago-Midway

Nov 2026
From$231*
Seen: 14 hrs ago
One Way/Basic
Dec 2026
From$125*
Seen: 11 hrs ago
One Way/Basic
Jan 2027
From$125*
Seen: 21 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $125
cmp-daily-histogram-bars-legend-max-price-aria-label $359
Displaying fares for November-2026
  • RDU–MDW, 11/12/2026: From $231
    12

    Thu

    NOV

  • RDU–MDW, 11/13/2026: From $231
    13

    Fri

  • RDU–MDW, 11/14/2026: From $231
    14

    Sat

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

    Sun

  • RDU–MDW, 11/16/2026: From $231
    16

    Mon

  • RDU–MDW, 11/17/2026: From $231
    17

    Tue

  • RDU–MDW, 11/18/2026: From $231
    18

    Wed

  • RDU–MDW, 11/19/2026: From $231
    19

    Thu

  • RDU–MDW, 11/20/2026: From $231
    20

    Fri

  • RDU–MDW, 11/21/2026: From $231
    21

    Sat

  • RDU–MDW, 11/22/2026: From $231
    22

    Sun

  • RDU–MDW, 11/23/2026: From $231
    23

    Mon

  • RDU–MDW, 11/24/2026: From $231
    24

    Tue

  • RDU–MDW, 11/25/2026: From $231
    25

    Wed

  • RDU–MDW, 11/26/2026: From $231
    26

    Thu

  • RDU–MDW, 11/27/2026: From $231
    27

    Fri

  • RDU–MDW, 11/28/2026: From $359
    28

    Sat

  • RDU–MDW, 11/29/2026: From $309
    29

    Sun

  • RDU–MDW, 11/30/2026: From $231
    30

    Mon

  • RDU–MDW, 12/01/2026: From $231
    01

    Tue

    DEC

  • RDU–MDW, 12/02/2026: From $125
    02

    Wed

  • RDU–MDW, 12/03/2026: From $145
    03

    Thu

  • RDU–MDW, 12/04/2026: From $160
    04

    Fri

  • RDU–MDW, 12/05/2026: From $125
    05

    Sat

  • RDU–MDW, 12/06/2026: From $231
    06

    Sun

  • RDU–MDW, 12/07/2026: From $145
    07

    Mon

  • RDU–MDW, 12/08/2026: From $125
    08

    Tue

  • RDU–MDW, 12/09/2026: From $125
    09

    Wed

  • RDU–MDW, 12/10/2026: From $145
    10

    Thu

  • RDU–MDW, 12/11/2026: From $160
    11

    Fri

    • Range$125-$359

    *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:
    Raleigh/Durham Airport
    Arriving at:
    Chicago Midway International Airport
    Average flight time:
    1 hour 57 minutes
    Distance:
    632 miles

    Questions we hear the most

    The average flight time from Raleigh/Durham to Chicago (Midway) is 1 hour 57 minutes.
    There are 153 weekly flights from Raleigh/Durham to Chicago (Midway) on Southwest Airlines.
    Yes, Southwest flies nonstop from Raleigh/Durham to Chicago (Midway) 2 times per day from Monday through Friday.
    Yes, Southwest flies nonstop from Raleigh/Durham to Chicago (Midway) 2 times per day on Saturdays and 3 times per day on Sundays.
    To find the lowest fares by day and time to fly Raleigh/Durham 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 Raleigh/Durham 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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