Southwest® flights from Raleigh/Durham to Chicago (O'Hare)

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Low fares from Raleigh/Durham to Chicago (O'Hare)

$

Raleigh/Durham (RDU)to

Chicago (Midway) (MDW)
Depart: 11/05/2026

One-way

Basic

From
$134
Seen: 14 hrs ago

Raleigh/Durham (RDU)to

Chicago (Midway) (MDW)
Depart: 10/14/2026

One-way

Basic

From
$134
Seen: 12 hrs ago

Raleigh/Durham (RDU)to

Chicago (Midway) (MDW)
Depart: 11/14/2026

One-way

Basic

From
$134
Seen: 9 hrs ago

Raleigh/Durham (RDU)to

Chicago (Midway) (MDW)
Depart: 09/23/2026

One-way

Basic

From
$134
Seen: 7 hrs ago

Raleigh/Durham (RDU)to

Chicago (Midway) (MDW)
Depart: 11/09/2026

One-way

Basic

From
$134
Seen: 7 hrs ago

Raleigh/Durham (RDU)to

Chicago (Midway) (MDW)
Depart: 09/21/2026

One-way

Basic

From
$134
Seen: 4 hrs ago

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Explore flights from Raleigh/Durham to Chicago (O'Hare)

Aug 2026
From$232*
Seen: 3 hrs ago
One Way/Basic
Sep 2026
From$134*
Seen: 2 hrs ago
One Way/Basic
Oct 2026
From$134*
Seen: 8 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $134
cmp-daily-histogram-bars-legend-max-price-aria-label $260
Displaying fares for August-2026
  • RDU–MDW, 08/26/2026: From $232
    26

    Wed

    AUG

  • RDU–MDW, 08/27/2026: From $250
    27

    Thu

  • RDU–MDW, 08/28/2026: From $260
    28

    Fri

  • RDU–MDW, 08/29/2026: From $232
    29

    Sat

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

    Sun

  • RDU–MDW, 08/31/2026: From $250
    31

    Mon

  • RDU–MDW, 09/01/2026: From $232
    01

    Tue

    SEP

  • RDU–MDW, 09/02/2026: From $232
    02

    Wed

  • RDU–MDW, 09/03/2026: From $260
    03

    Thu

  • RDU–MDW, 09/04/2026: From $250
    04

    Fri

  • RDU–MDW, 09/05/2026: From $175
    05

    Sat

  • RDU–MDW, 09/06/2026: From $175
    06

    Sun

  • RDU–MDW, 09/07/2026: From $250
    07

    Mon

  • RDU–MDW, 09/08/2026: From $222
    08

    Tue

  • RDU–MDW, 09/09/2026: From $175
    09

    Wed

  • RDU–MDW, 09/10/2026: From $185
    10

    Thu

  • RDU–MDW, 09/11/2026: From $175
    11

    Fri

  • RDU–MDW, 09/12/2026: From $175
    12

    Sat

  • RDU–MDW, 09/13/2026: From $250
    13

    Sun

  • RDU–MDW, 09/14/2026: From $250
    14

    Mon

  • RDU–MDW, 09/15/2026: From $134
    15

    Tue

  • RDU–MDW, 09/16/2026: From $134
    16

    Wed

  • RDU–MDW: cmp-view-offers-disclaimer. Find Offers
    17

    Thu

  • RDU–MDW, 09/18/2026: From $151
    18

    Fri

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

    Sat

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

    Sun

  • RDU–MDW, 09/21/2026: From $134
    21

    Mon

  • RDU–MDW, 09/22/2026: From $134
    22

    Tue

  • RDU–MDW, 09/23/2026: From $134
    23

    Wed

  • RDU–MDW, 09/24/2026: From $144
    24

    Thu

  • RDU–MDW, 09/25/2026: From $151
    25

    Fri

    • Range$134-$260

    *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:
    O'Hare International Airport
    Distance:
    646 miles

    Route Information

    44† Weekly flights

    † 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

    There are 44 weekly flights from Raleigh/Durham to Chicago (O'Hare) on Southwest Airlines.
    To find the lowest fares by day and time to fly Raleigh/Durham to Chicago (O'Hare) with Southwest, check out our Low Fare Calendar.
    You can rent a car at O'Hare International Airport book yours with your flight.
    Yes! Flights from Raleigh/Durham to Chicago (O'Hare)—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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