Southwest® flights from Raleigh/Durham to Chicago-Midway from $129

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Low fares from Raleigh/Durham to Chicago-Midway

$

Raleigh/Durham (RDU)to

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

One-way

Basic

From
$129
Seen: 20 hrs ago

Raleigh/Durham (RDU)to

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

One-way

Basic

From
$129
Seen: 21 hrs ago

Raleigh/Durham (RDU)to

Chicago-Midway (MDW)
Depart: 12/14/2026

One-way

Basic

From
$129
Seen: 16 hrs ago

Raleigh/Durham (RDU)to

Chicago-Midway (MDW)
Depart: 12/16/2026

One-way

Basic

From
$129
Seen: 13 hrs ago

Raleigh/Durham (RDU)to

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

One-way

Basic

From
$129
Seen: 12 hrs ago

Raleigh/Durham (RDU)to

Chicago-Midway (MDW)
Depart: 12/03/2026

One-way

Basic

From
$129
Seen: 20 hrs ago

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Explore flights from Raleigh/Durham to Chicago-Midway

Oct 2026
From$139*
Seen: 14 hrs ago
One Way/Basic
Nov 2026
From$129*
Seen: 17 hrs ago
One Way/Basic
Dec 2026
From$129*
Seen: 13 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $139
cmp-daily-histogram-bars-legend-max-price-aria-label $294
Displaying fares for October-2026
  • RDU–MDW, 10/03/2026: From $242
    03

    Sat

    OCT

  • RDU–MDW, 10/04/2026: From $294
    04

    Sun

  • RDU–MDW, 10/05/2026: From $270
    05

    Mon

  • RDU–MDW, 10/06/2026: From $242
    06

    Tue

  • RDU–MDW, 10/07/2026: From $242
    07

    Wed

  • RDU–MDW, 10/08/2026: From $270
    08

    Thu

  • RDU–MDW, 10/09/2026: From $294
    09

    Fri

  • RDU–MDW, 10/10/2026: From $242
    10

    Sat

  • RDU–MDW, 10/11/2026: From $270
    11

    Sun

  • RDU–MDW: cmp-view-offers-disclaimer. Find Offers
    12

    Mon

  • RDU–MDW, 10/13/2026: From $242
    13

    Tue

  • RDU–MDW, 10/14/2026: From $270
    14

    Wed

  • RDU–MDW, 10/15/2026: From $270
    15

    Thu

  • RDU–MDW, 10/16/2026: From $270
    16

    Fri

  • RDU–MDW, 10/17/2026: From $242
    17

    Sat

  • RDU–MDW, 10/18/2026: From $270
    18

    Sun

  • RDU–MDW, 10/19/2026: From $270
    19

    Mon

  • RDU–MDW: cmp-view-offers-disclaimer. Find Offers
    20

    Tue

  • RDU–MDW, 10/21/2026: From $242
    21

    Wed

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

    Thu

  • RDU–MDW, 10/23/2026: From $166
    23

    Fri

  • RDU–MDW, 10/24/2026: From $166
    24

    Sat

  • RDU–MDW, 10/25/2026: From $237
    25

    Sun

  • RDU–MDW, 10/26/2026: From $139
    26

    Mon

  • RDU–MDW, 10/27/2026: From $166
    27

    Tue

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

    Wed

  • RDU–MDW, 10/29/2026: From $166
    29

    Thu

  • RDU–MDW, 10/30/2026: From $166
    30

    Fri

  • RDU–MDW: cmp-view-offers-disclaimer. Find Offers
    31

    Sat

  • RDU–MDW: cmp-view-offers-disclaimer. Find Offers
    01

    Sun

    NOV

  • RDU–MDW: cmp-view-offers-disclaimer. Find Offers
    02

    Mon

    • Range$139-$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

    Route Information

    153† Weekly flights
    • 2‡ Nonstop flights per day Monday through Friday
    • 2‡ Nonstop flights 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 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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