Southwest® flights from Norfolk/Virginia Beach to Chicago (Midway) from $139

Promo Code

Low fares from Norfolk/Virginia Beach to Chicago (Midway)

$

Norfolk/Virginia Beach (ORF)to

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

One-way

Basic

From
$139
Seen: 18 hrs ago

Norfolk/Virginia Beach (ORF)to

Chicago (Midway) (MDW)
Depart: 11/18/2026

One-way

Basic

From
$139
Seen: 19 hrs ago

Norfolk/Virginia Beach (ORF)to

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

One-way

Basic

From
$139
Seen: 14 hrs ago

Norfolk/Virginia Beach (ORF)to

Chicago (Midway) (MDW)
Depart: 10/17/2026

One-way

Basic

From
$139
Seen: 6 hrs ago

Norfolk/Virginia Beach (ORF)to

Chicago (Midway) (MDW)
Depart: 09/29/2026

One-way

Basic

From
$139
Seen: 11 hrs ago

Norfolk/Virginia Beach (ORF)to

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

One-way

Basic

From
$139
Seen: 8 hrs ago

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Explore flights from Norfolk/Virginia Beach to Chicago (Midway)

Aug 2026
From$251*
Seen: 4 hrs ago
One Way/Basic
Sep 2026
From$139*
Seen: 14 hrs ago
One Way/Basic
Oct 2026
From$139*
Seen: 9 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $139
cmp-daily-histogram-bars-legend-max-price-aria-label $279
Displaying fares for August-2026
  • ORF–MDW, 08/20/2026: From $279
    20

    Thu

    AUG

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

    Fri

  • ORF–MDW, 08/22/2026: From $251
    22

    Sat

  • ORF–MDW, 08/23/2026: From $279
    23

    Sun

  • ORF–MDW, 08/24/2026: From $279
    24

    Mon

  • ORF–MDW, 08/25/2026: From $251
    25

    Tue

  • ORF–MDW, 08/26/2026: From $251
    26

    Wed

  • ORF–MDW, 08/27/2026: From $279
    27

    Thu

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

    Fri

  • ORF–MDW, 08/29/2026: From $251
    29

    Sat

  • ORF–MDW, 08/30/2026: From $279
    30

    Sun

  • ORF–MDW, 08/31/2026: From $279
    31

    Mon

  • ORF–MDW, 09/01/2026: From $251
    01

    Tue

    SEP

  • ORF–MDW, 09/02/2026: From $251
    02

    Wed

  • ORF–MDW, 09/03/2026: From $265
    03

    Thu

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

    Fri

  • ORF–MDW, 09/05/2026: From $202
    05

    Sat

  • ORF–MDW: cmp-view-offers-disclaimer. Find Offers
    06

    Sun

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

    Mon

  • ORF–MDW, 09/08/2026: From $250
    08

    Tue

  • ORF–MDW, 09/09/2026: From $202
    09

    Wed

  • ORF–MDW, 09/10/2026: From $139
    10

    Thu

  • ORF–MDW, 09/11/2026: From $158
    11

    Fri

  • ORF–MDW, 09/12/2026: From $139
    12

    Sat

  • ORF–MDW, 09/13/2026: From $238
    13

    Sun

  • ORF–MDW, 09/14/2026: From $139
    14

    Mon

  • ORF–MDW: cmp-view-offers-disclaimer. Find Offers
    15

    Tue

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

    Wed

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

    Thu

  • ORF–MDW, 09/18/2026: From $158
    18

    Fri

  • ORF–MDW, 09/19/2026: From $158
    19

    Sat

    • Range$139-$279

    *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:
    Norfolk International Airport
    Arriving at:
    Chicago Midway International Airport
    Average flight time:
    2 hours 9 minutes
    Distance:
    704 miles

    Route Information

    106† Weekly flights
    • 2‡ Nonstop flights per day Monday through Friday
    • 1‡ Nonstop flight on Saturday
    • 2‡ 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 Norfolk/Virginia Beach to Chicago (Midway) is 2 hours 9 minutes.
    There are 106 weekly flights from Norfolk/Virginia Beach to Chicago (Midway) on Southwest Airlines.
    Yes, Southwest flies nonstop from Norfolk/Virginia Beach to Chicago (Midway) 2 times per day from Monday through Friday.
    Yes, Southwest flies nonstop from Norfolk/Virginia Beach to Chicago (Midway) once per day on Saturdays and 2 times per day on Sundays.
    To find the lowest fares by day and time to fly Norfolk/Virginia Beach 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 Norfolk/Virginia Beach 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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