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: 10/30/2026

One-way

Basic

From
$104
Seen: 18 hrs ago

Raleigh/Durham (RDU)to

Chicago (Midway) (MDW)
Depart: 09/06/2026

One-way

Basic

From
$104
Seen: 8 hrs ago

Raleigh/Durham (RDU)to

Chicago (Midway) (MDW)
Depart: 09/05/2026

One-way

Basic

From
$104
Seen: 14 hrs ago

Raleigh/Durham (RDU)to

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

One-way

Basic

From
$104
Seen: 4 hrs ago

Raleigh/Durham (RDU)to

Chicago (Midway) (MDW)
Depart: 08/25/2026

One-way

Basic

From
$118
Seen: 21 hrs ago

Raleigh/Durham (RDU)to

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

One-way

Basic

From
$118
Seen: 10 hrs ago

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

Aug 2026
From$118*
Seen: 21 hrs ago
One Way/Basic
Sep 2026
From$104*
Seen: 8 hrs ago
One Way/Basic
Oct 2026
From$104*
Seen: 18 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $104
cmp-daily-histogram-bars-legend-max-price-aria-label $281
Displaying fares for August-2026
  • RDU–MDW, 08/06/2026: From $281
    06

    Thu

    AUG

  • RDU–MDW, 08/07/2026: From $264
    07

    Fri

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

    Sat

  • RDU–MDW, 08/09/2026: From $264
    09

    Sun

  • RDU–MDW: cmp-view-offers-disclaimer. Find Offers
    10

    Mon

  • RDU–MDW, 08/11/2026: From $222
    11

    Tue

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

    Wed

  • RDU–MDW, 08/13/2026: From $264
    13

    Thu

  • RDU–MDW, 08/14/2026: From $264
    14

    Fri

  • RDU–MDW, 08/15/2026: From $222
    15

    Sat

  • RDU–MDW, 08/16/2026: From $264
    16

    Sun

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    17

    Mon

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

    Tue

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

    Wed

  • RDU–MDW, 08/20/2026: From $250
    20

    Thu

  • RDU–MDW: cmp-view-offers-disclaimer. Find Offers
    21

    Fri

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

    Sat

  • RDU–MDW, 08/23/2026: From $250
    23

    Sun

  • RDU–MDW, 08/24/2026: From $250
    24

    Mon

  • RDU–MDW, 08/25/2026: From $118
    25

    Tue

  • RDU–MDW, 08/26/2026: From $118
    26

    Wed

  • RDU–MDW, 08/27/2026: From $128
    27

    Thu

  • RDU–MDW, 08/28/2026: From $146
    28

    Fri

  • RDU–MDW: cmp-view-offers-disclaimer. Find Offers
    29

    Sat

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

    Sun

  • RDU–MDW, 08/31/2026: From $118
    31

    Mon

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

    Tue

    SEP

  • RDU–MDW, 09/02/2026: From $118
    02

    Wed

  • RDU–MDW, 09/03/2026: From $227
    03

    Thu

  • RDU–MDW, 09/04/2026: From $156
    04

    Fri

  • RDU–MDW, 09/05/2026: From $104
    05

    Sat

    • Range$104-$281

    *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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