Southwest® flights from Norfolk/Virginia Beach to Chicago (O'Hare)

Promo Code

Low fares from Norfolk/Virginia Beach to Chicago (O'Hare)

$

Norfolk/Virginia Beach (ORF)to

Chicago (Midway) (MDW)
Depart: 10/30/2026

One-way

Basic

From
$159
Seen: 10 hrs ago

Norfolk/Virginia Beach (ORF)to

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

One-way

Basic

From
$159
Seen: 4 hrs ago

Norfolk/Virginia Beach (ORF)to

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

One-way

Basic

From
$173
Seen: 19 hrs ago

Norfolk/Virginia Beach (ORF)to

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

One-way

Basic

From
$173
Seen: 8 hrs ago

Norfolk/Virginia Beach (ORF)to

Chicago (Midway) (MDW)
Depart: 09/19/2026

One-way

Basic

From
$173
Seen: 15 hrs ago

Norfolk/Virginia Beach (ORF)to

Chicago (Midway) (MDW)
Depart: 08/25/2026

One-way

Basic

From
$173
Seen: 9 hrs ago

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Explore flights from Norfolk/Virginia Beach to Chicago (O'Hare)

Aug 2026
From$173*
Seen: 14 hrs ago
One Way/Basic
Sep 2026
From$159*
Seen: 4 hrs ago
One Way/Basic
Oct 2026
From$159*
Seen: 10 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $173
cmp-daily-histogram-bars-legend-max-price-aria-label $398
Displaying fares for August-2026
  • ORF–MDW, 08/05/2026: From $286
    05

    Wed

    AUG

  • ORF–MDW, 08/06/2026: From $337
    06

    Thu

  • ORF–MDW, 08/07/2026: From $398
    07

    Fri

  • ORF–MDW, 08/08/2026: From $214
    08

    Sat

  • ORF–MDW, 08/09/2026: From $327
    09

    Sun

  • ORF–MDW, 08/10/2026: From $279
    10

    Mon

  • ORF–MDW, 08/11/2026: From $251
    11

    Tue

  • ORF–MDW, 08/12/2026: From $251
    12

    Wed

  • ORF–MDW: cmp-view-offers-disclaimer. Find Offers
    13

    Thu

  • ORF–MDW, 08/14/2026: From $279
    14

    Fri

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

    Sat

  • ORF–MDW, 08/16/2026: From $289
    16

    Sun

  • ORF–MDW, 08/17/2026: From $279
    17

    Mon

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

    Tue

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

    Wed

  • ORF–MDW, 08/20/2026: From $250
    20

    Thu

  • ORF–MDW, 08/21/2026: From $250
    21

    Fri

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    22

    Sat

  • ORF–MDW: cmp-view-offers-disclaimer. Find Offers
    23

    Sun

  • ORF–MDW: cmp-view-offers-disclaimer. Find Offers
    24

    Mon

  • ORF–MDW, 08/25/2026: From $173
    25

    Tue

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

    Wed

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

    Thu

  • ORF–MDW, 08/28/2026: From $180
    28

    Fri

  • ORF–MDW, 08/29/2026: From $173
    29

    Sat

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    30

    Sun

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    31

    Mon

  • ORF–MDW: cmp-view-offers-disclaimer. Find Offers
    01

    Tue

    SEP

  • ORF–MDW, 09/02/2026: From $173
    02

    Wed

  • ORF–MDW, 09/03/2026: From $223
    03

    Thu

  • ORF–MDW, 09/04/2026: From $180
    04

    Fri

    • Range$173-$398

    *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:
    O'Hare International Airport
    Distance:
    717 miles

    Route Information

    18† Weekly flights

    † 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

    There are 18 weekly flights from Norfolk/Virginia Beach to Chicago (O'Hare) on Southwest Airlines.
    To find the lowest fares by day and time to fly Norfolk/Virginia Beach to Chicago (O'Hare) with Southwest, check out our Low Fare Calendar.
    You can rent a car at O'Hare International Airport book yours with your flight.
    Yes! Flights from Norfolk/Virginia Beach to Chicago (O'Hare)—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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