Southwest® flights from Raleigh/Durham to Chicago-Midway from $113

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Low fares from Raleigh/Durham to Chicago-Midway

$

Raleigh/Durham (RDU)to

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

One-way

Basic

From
$113
Seen: 2 hrs ago

Raleigh/Durham (RDU)to

Chicago-Midway (MDW)
Depart: 11/13/2026

One-way

Basic

From
$113
Seen: 42 minutes ago

Raleigh/Durham (RDU)to

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

One-way

Basic

From
$113
Seen: 25 minutes ago

Raleigh/Durham (RDU)to

Chicago-Midway (MDW)
Depart: 11/12/2026

One-way

Basic

From
$113
Seen: 1 hour ago

Raleigh/Durham (RDU)to

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

One-way

Basic

From
$114
Seen: 17 hrs ago

Raleigh/Durham (RDU)to

Chicago-Midway (MDW)
Depart: 12/11/2026

One-way

Basic

From
$114
Seen: 13 hrs ago

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Explore flights from Raleigh/Durham to Chicago-Midway

Oct 2026
From$252*
Seen: 12 hrs ago
One Way/Basic
Nov 2026
From$113*
Seen: 42 minutes ago
One Way/Basic
Dec 2026
From$113*
Seen: 2 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $113
cmp-daily-histogram-bars-legend-max-price-aria-label $294
Displaying fares for October-2026
  • RDU–MDW, 10/24/2026: From $252
    24

    Sat

    OCT

  • RDU–MDW, 10/25/2026: From $280
    25

    Sun

  • RDU–MDW, 10/26/2026: From $280
    26

    Mon

  • RDU–MDW, 10/27/2026: From $252
    27

    Tue

  • RDU–MDW: cmp-view-offers-disclaimer. Find Offers
    28

    Wed

  • RDU–MDW, 10/29/2026: From $280
    29

    Thu

  • RDU–MDW, 10/30/2026: From $280
    30

    Fri

  • RDU–MDW, 10/31/2026: From $252
    31

    Sat

  • RDU–MDW, 11/01/2026: From $280
    01

    Sun

    NOV

  • RDU–MDW, 11/02/2026: From $280
    02

    Mon

  • RDU–MDW: cmp-view-offers-disclaimer. Find Offers
    03

    Tue

  • RDU–MDW, 11/04/2026: From $252
    04

    Wed

  • RDU–MDW, 11/05/2026: From $294
    05

    Thu

  • RDU–MDW, 11/06/2026: From $280
    06

    Fri

  • RDU–MDW, 11/07/2026: From $252
    07

    Sat

  • RDU–MDW, 11/08/2026: From $280
    08

    Sun

  • RDU–MDW, 11/09/2026: From $114
    09

    Mon

  • RDU–MDW, 11/10/2026: From $114
    10

    Tue

  • RDU–MDW, 11/11/2026: From $113
    11

    Wed

  • RDU–MDW, 11/12/2026: From $113
    12

    Thu

  • RDU–MDW, 11/13/2026: From $113
    13

    Fri

  • RDU–MDW, 11/14/2026: From $124
    14

    Sat

  • RDU–MDW, 11/15/2026: From $247
    15

    Sun

  • RDU–MDW: cmp-view-offers-disclaimer. Find Offers
    16

    Mon

  • RDU–MDW, 11/17/2026: From $114
    17

    Tue

  • RDU–MDW, 11/18/2026: From $114
    18

    Wed

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

    Thu

  • RDU–MDW, 11/20/2026: From $201
    20

    Fri

  • RDU–MDW, 11/21/2026: From $114
    21

    Sat

  • RDU–MDW: cmp-view-offers-disclaimer. Find Offers
    22

    Sun

  • RDU–MDW, 11/23/2026: From $124
    23

    Mon

    • Range$113-$294

    *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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