Southwest® flights from Norfolk/Virginia Beach to Chicago-Midway from $136

Promo Code

Low fares from Norfolk/Virginia Beach to Chicago-Midway

$

Norfolk/Virginia Beach (ORF)to

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

One-way

Basic

From
$136
Seen: 22 hrs ago

Norfolk/Virginia Beach (ORF)to

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

One-way

Basic

From
$136
Seen: 12 hrs ago

Norfolk/Virginia Beach (ORF)to

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

One-way

Basic

From
$136
Seen: 10 hrs ago

Norfolk/Virginia Beach (ORF)to

Chicago-Midway (MDW)
Depart: 12/08/2026

One-way

Basic

From
$136
Seen: 9 hrs ago

Norfolk/Virginia Beach (ORF)to

Chicago-Midway (MDW)
Depart: 01/06/2027

One-way

Basic

From
$136
Seen: 22 hrs ago

Norfolk/Virginia Beach (ORF)to

Chicago-Midway (MDW)
Depart: 12/05/2026

One-way

Basic

From
$136
Seen: 16 hrs ago

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Explore flights from Norfolk/Virginia Beach to Chicago-Midway

Oct 2026
From$271*
Seen: 6 hrs ago
One Way/Basic
Nov 2026
From$136*
Seen: 22 hrs ago
One Way/Basic
Dec 2026
From$136*
Seen: 16 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $136
cmp-daily-histogram-bars-legend-max-price-aria-label $319
Displaying fares for October-2026
  • ORF–MDW, 10/21/2026: From $294
    21

    Wed

    OCT

  • ORF–MDW, 10/22/2026: From $309
    22

    Thu

  • ORF–MDW, 10/23/2026: From $319
    23

    Fri

  • ORF–MDW, 10/24/2026: From $271
    24

    Sat

  • ORF–MDW: cmp-view-offers-disclaimer. Find Offers
    25

    Sun

  • ORF–MDW: cmp-view-offers-disclaimer. Find Offers
    26

    Mon

  • ORF–MDW, 10/27/2026: From $271
    27

    Tue

  • ORF–MDW, 10/28/2026: From $271
    28

    Wed

  • ORF–MDW, 10/29/2026: From $309
    29

    Thu

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

    Fri

  • ORF–MDW, 10/31/2026: From $279
    31

    Sat

  • ORF–MDW, 11/01/2026: From $309
    01

    Sun

    NOV

  • ORF–MDW, 11/02/2026: From $319
    02

    Mon

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

    Tue

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

    Wed

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

    Thu

  • ORF–MDW, 11/06/2026: From $290
    06

    Fri

  • ORF–MDW, 11/07/2026: From $271
    07

    Sat

  • ORF–MDW: cmp-view-offers-disclaimer. Find Offers
    08

    Sun

  • ORF–MDW: cmp-view-offers-disclaimer. Find Offers
    09

    Mon

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

    Tue

  • ORF–MDW, 11/11/2026: From $146
    11

    Wed

  • ORF–MDW, 11/12/2026: From $146
    12

    Thu

  • ORF–MDW, 11/13/2026: From $299
    13

    Fri

  • ORF–MDW, 11/14/2026: From $136
    14

    Sat

  • ORF–MDW, 11/15/2026: From $156
    15

    Sun

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

    Mon

  • ORF–MDW, 11/17/2026: From $136
    17

    Tue

  • ORF–MDW, 11/18/2026: From $136
    18

    Wed

  • ORF–MDW, 11/19/2026: From $146
    19

    Thu

  • ORF–MDW, 11/20/2026: From $186
    20

    Fri

    • Range$136-$319

    *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

    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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