Southwest® flights from Richmond to Chicago (O'Hare)

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Low fares from Richmond to Chicago (O'Hare)

$

Richmond (RIC)to

Chicago (Midway) (MDW)
Depart: 08/31/2026

One-way

Basic

From
$106
Seen: 15 hrs ago

Richmond (RIC)to

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

One-way

Basic

From
$119
Seen: 15 hrs ago

Richmond (RIC)to

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

One-way

Basic

From
$129
Seen: 22 hrs ago

Richmond (RIC)to

Chicago (Midway) (MDW)
Depart: 11/05/2026

One-way

Basic

From
$129
Seen: 15 hrs ago

Richmond (RIC)to

Chicago (Midway) (MDW)
Depart: 09/15/2026

One-way

Basic

From
$129
Seen: 6 hrs ago

Richmond (RIC)to

Chicago (Midway) (MDW)
Depart: 08/29/2026

One-way

Basic

From
$129
Seen: 15 hrs ago

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Explore flights from Richmond to Chicago (O'Hare)

Aug 2026
From$106*
Seen: 15 hrs ago
One Way/Basic
Sep 2026
From$119*
Seen: 15 hrs ago
One Way/Basic
Oct 2026
From$129*
Seen: 15 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $106
cmp-daily-histogram-bars-legend-max-price-aria-label $310
Displaying fares for August-2026
  • RIC–MDW, 08/04/2026: From $241
    04

    Tue

    AUG

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

    Wed

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

    Thu

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    07

    Fri

  • RIC–MDW, 08/08/2026: From $196
    08

    Sat

  • RIC–MDW, 08/09/2026: From $310
    09

    Sun

  • RIC–MDW, 08/10/2026: From $270
    10

    Mon

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

    Tue

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

    Wed

  • RIC–MDW, 08/13/2026: From $280
    13

    Thu

  • RIC–MDW, 08/14/2026: From $270
    14

    Fri

  • RIC–MDW, 08/15/2026: From $241
    15

    Sat

  • RIC–MDW, 08/16/2026: From $270
    16

    Sun

  • RIC–MDW, 08/17/2026: From $238
    17

    Mon

  • RIC–MDW, 08/18/2026: From $238
    18

    Tue

  • RIC–MDW, 08/19/2026: From $238
    19

    Wed

  • RIC–MDW, 08/20/2026: From $238
    20

    Thu

  • RIC–MDW, 08/21/2026: From $238
    21

    Fri

  • RIC–MDW, 08/22/2026: From $238
    22

    Sat

  • RIC–MDW, 08/23/2026: From $238
    23

    Sun

  • RIC–MDW, 08/24/2026: From $238
    24

    Mon

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

    Tue

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

    Wed

  • RIC–MDW, 08/27/2026: From $139
    27

    Thu

  • RIC–MDW, 08/28/2026: From $175
    28

    Fri

  • RIC–MDW, 08/29/2026: From $129
    29

    Sat

  • RIC–MDW, 08/30/2026: From $210
    30

    Sun

  • RIC–MDW, 08/31/2026: From $106
    31

    Mon

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

    Tue

    SEP

  • RIC–MDW, 09/02/2026: From $129
    02

    Wed

  • RIC–MDW, 09/03/2026: From $210
    03

    Thu

    • Range$106-$310

    *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:
    Richmond International Airport
    Arriving at:
    O'Hare International Airport
    Distance:
    642 miles

    Route Information

    49† 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 49 weekly flights from Richmond to Chicago (O'Hare) on Southwest Airlines.
    To find the lowest fares by day and time to fly Richmond 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 Richmond 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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