Southwest® flights from Norfolk/Virginia Beach to Chicago-Midway from $159

Promo Code

Low fares from Norfolk/Virginia Beach to Chicago-Midway

$

Norfolk/Virginia Beach (ORF)to

Chicago-Midway (MDW)
Depart: 01/05/2027

One-way

Basic

From
$159
Seen: 9 hrs ago

Norfolk/Virginia Beach (ORF)to

Chicago-Midway (MDW)
Depart: 12/02/2026

One-way

Basic

From
$159
Seen: 12 hrs ago

Norfolk/Virginia Beach (ORF)to

Chicago-Midway (MDW)
Depart: 11/17/2026

One-way

Basic

From
$159
Seen: 1 hour ago

Norfolk/Virginia Beach (ORF)to

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

One-way

Basic

From
$159
Seen: 21 hrs ago

Norfolk/Virginia Beach (ORF)to

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

One-way

Basic

From
$159
Seen: 23 hrs ago

Norfolk/Virginia Beach (ORF)to

Chicago-Midway (MDW)
Depart: 10/29/2026

One-way

Basic

From
$159
Seen: 18 hrs ago

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Explore flights from Norfolk/Virginia Beach to Chicago-Midway

Oct 2026
From$159*
Seen: 23 hrs ago
One Way/Basic
Nov 2026
From$159*
Seen: 11 hrs ago
One Way/Basic
Dec 2026
From$159*
Seen: 48 minutes ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $159
cmp-daily-histogram-bars-legend-max-price-aria-label $362
Displaying fares for October-2026
  • ORF–MDW, 10/01/2026: From $309
    01

    Thu

    OCT

  • ORF–MDW, 10/02/2026: From $309
    02

    Fri

  • ORF–MDW, 10/03/2026: From $271
    03

    Sat

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

    Sun

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

    Mon

  • ORF–MDW, 10/06/2026: From $271
    06

    Tue

  • ORF–MDW, 10/07/2026: From $271
    07

    Wed

  • ORF–MDW, 10/08/2026: From $331
    08

    Thu

  • ORF–MDW, 10/09/2026: From $362
    09

    Fri

  • ORF–MDW, 10/10/2026: From $271
    10

    Sat

  • ORF–MDW, 10/11/2026: From $331
    11

    Sun

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

    Mon

  • ORF–MDW, 10/13/2026: From $271
    13

    Tue

  • ORF–MDW, 10/14/2026: From $270
    14

    Wed

  • ORF–MDW, 10/15/2026: From $270
    15

    Thu

  • ORF–MDW, 10/16/2026: From $270
    16

    Fri

  • ORF–MDW, 10/17/2026: From $270
    17

    Sat

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

    Sun

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

    Mon

  • ORF–MDW, 10/20/2026: From $270
    20

    Tue

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

    Wed

  • ORF–MDW, 10/22/2026: From $169
    22

    Thu

  • ORF–MDW, 10/23/2026: From $178
    23

    Fri

  • ORF–MDW, 10/24/2026: From $159
    24

    Sat

  • ORF–MDW, 10/25/2026: From $300
    25

    Sun

  • ORF–MDW, 10/26/2026: From $188
    26

    Mon

  • ORF–MDW: cmp-view-offers-disclaimer. Find Offers
    27

    Tue

  • ORF–MDW, 10/28/2026: From $159
    28

    Wed

  • ORF–MDW, 10/29/2026: From $159
    29

    Thu

  • ORF–MDW, 10/30/2026: From $178
    30

    Fri

  • ORF–MDW: cmp-view-offers-disclaimer. Find Offers
    31

    Sat

    • Range$159-$362

    *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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