Southwest® flights from Norfolk/Virginia Beach to Chicago-Midway from $151

Promo Code

Low fares from Norfolk/Virginia Beach to Chicago-Midway

$

Norfolk/Virginia Beach (ORF)to

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

One-way

Basic

From
$151
Seen: 9 hrs ago

Norfolk/Virginia Beach (ORF)to

Chicago-Midway (MDW)
Depart: 11/07/2026

One-way

Basic

From
$151
Seen: 10 hrs ago

Norfolk/Virginia Beach (ORF)to

Chicago-Midway (MDW)
Depart: 11/19/2026

One-way

Basic

From
$151
Seen: 10 hrs ago

Norfolk/Virginia Beach (ORF)to

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

One-way

Basic

From
$151
Seen: 13 hrs ago

Norfolk/Virginia Beach (ORF)to

Chicago-Midway (MDW)
Depart: 11/12/2026

One-way

Basic

From
$151
Seen: 10 hrs ago

Norfolk/Virginia Beach (ORF)to

Chicago-Midway (MDW)
Depart: 10/28/2026

One-way

Basic

From
$151
Seen: 8 hrs ago

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Explore flights from Norfolk/Virginia Beach to Chicago-Midway

Sep 2026
From$151*
Seen: 14 hrs ago
One Way/Basic
Oct 2026
From$151*
Seen: 8 hrs ago
One Way/Basic
Nov 2026
From$151*
Seen: 9 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $151
cmp-daily-histogram-bars-legend-max-price-aria-label $329
Displaying fares for September-2026
  • ORF–MDW, 09/10/2026: From $289
    10

    Thu

    SEP

  • ORF–MDW, 09/11/2026: From $289
    11

    Fri

  • ORF–MDW, 09/12/2026: From $261
    12

    Sat

  • ORF–MDW, 09/13/2026: From $329
    13

    Sun

  • ORF–MDW, 09/14/2026: From $289
    14

    Mon

  • ORF–MDW, 09/15/2026: From $261
    15

    Tue

  • ORF–MDW, 09/16/2026: From $261
    16

    Wed

  • ORF–MDW, 09/17/2026: From $299
    17

    Thu

  • ORF–MDW, 09/18/2026: From $289
    18

    Fri

  • ORF–MDW, 09/19/2026: From $261
    19

    Sat

  • ORF–MDW, 09/20/2026: From $299
    20

    Sun

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

    Mon

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

    Tue

  • ORF–MDW, 09/23/2026: From $260
    23

    Wed

  • ORF–MDW, 09/24/2026: From $265
    24

    Thu

  • ORF–MDW, 09/25/2026: From $260
    25

    Fri

  • ORF–MDW, 09/26/2026: From $260
    26

    Sat

  • ORF–MDW, 09/27/2026: From $309
    27

    Sun

  • ORF–MDW, 09/28/2026: From $260
    28

    Mon

  • ORF–MDW, 09/29/2026: From $260
    29

    Tue

  • ORF–MDW, 09/30/2026: From $151
    30

    Wed

  • ORF–MDW, 10/01/2026: From $151
    01

    Thu

    OCT

  • ORF–MDW, 10/02/2026: From $168
    02

    Fri

  • ORF–MDW: cmp-view-offers-disclaimer. Find Offers
    03

    Sat

  • ORF–MDW: cmp-view-offers-disclaimer. Find Offers
    04

    Sun

  • ORF–MDW: cmp-view-offers-disclaimer. Find Offers
    05

    Mon

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

    Tue

  • ORF–MDW: cmp-view-offers-disclaimer. Find Offers
    07

    Wed

  • ORF–MDW, 10/08/2026: From $183
    08

    Thu

  • ORF–MDW, 10/09/2026: From $233
    09

    Fri

    • Range$151-$329

    *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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