Southwest® flights from Raleigh/Durham to Chicago-Midway from $162

Promo Code

Low fares from Raleigh/Durham to Chicago-Midway

$

Raleigh/Durham (RDU)to

Chicago-Midway (MDW)
Depart: 11/27/2026

One-way

Basic

From
$162
Seen: 21 hrs ago

Raleigh/Durham (RDU)to

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

One-way

Basic

From
$162
Seen: 12 hrs ago

Raleigh/Durham (RDU)to

Chicago-Midway (MDW)
Depart: 12/09/2026

One-way

Basic

From
$162
Seen: 15 hrs ago

Raleigh/Durham (RDU)to

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

One-way

Basic

From
$162
Seen: 22 hrs ago

Raleigh/Durham (RDU)to

Chicago-Midway (MDW)
Depart: 11/26/2026

One-way

Basic

From
$162
Seen: 22 hrs ago

Raleigh/Durham (RDU)to

Chicago-Midway (MDW)
Depart: 10/24/2026

One-way

Basic

From
$162
Seen: 49 minutes ago

Looking for more low-fare flights?

Check out the Low Fare Calendar to find a fare that works for you. Just choose the month you want to depart and return, and we’ll show you the best fares available.

Find low fares

Explore flights from Raleigh/Durham to Chicago-Midway

Sep 2026
From$242*
Seen: 3 hrs ago
One Way/Basic
Oct 2026
From$162*
Seen: 49 minutes ago
One Way/Basic
Nov 2026
From$162*
Seen: 22 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $162
cmp-daily-histogram-bars-legend-max-price-aria-label $280
Displaying fares for September-2026
  • RDU–MDW, 09/12/2026: From $242
    12

    Sat

    SEP

  • RDU–MDW, 09/13/2026: From $270
    13

    Sun

  • RDU–MDW: cmp-view-offers-disclaimer. Find Offers
    14

    Mon

  • RDU–MDW, 09/15/2026: From $242
    15

    Tue

  • RDU–MDW, 09/16/2026: From $242
    16

    Wed

  • RDU–MDW, 09/17/2026: From $270
    17

    Thu

  • RDU–MDW, 09/18/2026: From $280
    18

    Fri

  • RDU–MDW, 09/19/2026: From $242
    19

    Sat

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

    Sun

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

    Mon

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

    Tue

  • RDU–MDW, 09/23/2026: From $242
    23

    Wed

  • RDU–MDW, 09/24/2026: From $270
    24

    Thu

  • RDU–MDW, 09/25/2026: From $270
    25

    Fri

  • RDU–MDW, 09/26/2026: From $242
    26

    Sat

  • RDU–MDW, 09/27/2026: From $270
    27

    Sun

  • RDU–MDW, 09/28/2026: From $270
    28

    Mon

  • RDU–MDW, 09/29/2026: From $242
    29

    Tue

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

    Wed

  • RDU–MDW, 10/01/2026: From $270
    01

    Thu

    OCT

  • RDU–MDW, 10/02/2026: From $270
    02

    Fri

  • RDU–MDW, 10/03/2026: From $237
    03

    Sat

  • RDU–MDW, 10/04/2026: From $258
    04

    Sun

  • RDU–MDW, 10/05/2026: From $237
    05

    Mon

  • RDU–MDW, 10/06/2026: From $237
    06

    Tue

  • RDU–MDW, 10/07/2026: From $237
    07

    Wed

  • RDU–MDW, 10/08/2026: From $162
    08

    Thu

  • RDU–MDW, 10/09/2026: From $237
    09

    Fri

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

    Sat

  • RDU–MDW, 10/11/2026: From $194
    11

    Sun

    • Range$162-$280

    *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.

    Explore Flights from Other Popular Origins

    Popular Flights from Raleigh/Durham