Southwest® flights from Richmond to Chicago-Midway from $131

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Low fares from Richmond to Chicago-Midway

$

Richmond (RIC)to

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

One-way

Basic

From
$131
Seen: 13 hrs ago

Richmond (RIC)to

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

One-way

Basic

From
$131
Seen: 39 minutes ago

Richmond (RIC)to

Chicago-Midway (MDW)
Depart: 11/10/2026

One-way

Basic

From
$131
Seen: 21 hrs ago

Richmond (RIC)to

Chicago-Midway (MDW)
Depart: 12/06/2026

One-way

Basic

From
$131
Seen: 13 hrs ago

Richmond (RIC)to

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

One-way

Basic

From
$141
Seen: 21 hrs ago

Richmond (RIC)to

Chicago-Midway (MDW)
Depart: 11/23/2026

One-way

Basic

From
$141
Seen: 8 hrs ago

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Explore flights from Richmond to Chicago-Midway

Oct 2026
From$269*
Seen: 12 hrs ago
One Way/Basic
Nov 2026
From$131*
Seen: 21 hrs ago
One Way/Basic
Dec 2026
From$131*
Seen: 13 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $131
cmp-daily-histogram-bars-legend-max-price-aria-label $344
Displaying fares for October-2026
  • RIC–MDW, 10/22/2026: From $300
    22

    Thu

    OCT

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

    Fri

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

    Sat

  • RIC–MDW, 10/25/2026: From $344
    25

    Sun

  • RIC–MDW, 10/26/2026: From $300
    26

    Mon

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

    Tue

  • RIC–MDW, 10/28/2026: From $269
    28

    Wed

  • RIC–MDW, 10/29/2026: From $300
    29

    Thu

  • RIC–MDW, 10/30/2026: From $300
    30

    Fri

  • RIC–MDW, 10/31/2026: From $269
    31

    Sat

  • RIC–MDW, 11/01/2026: From $310
    01

    Sun

    NOV

  • RIC–MDW, 11/02/2026: From $310
    02

    Mon

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

    Tue

  • RIC–MDW, 11/04/2026: From $268
    04

    Wed

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

    Thu

  • RIC–MDW, 11/06/2026: From $278
    06

    Fri

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

    Sat

  • RIC–MDW, 11/08/2026: From $268
    08

    Sun

  • RIC–MDW, 11/09/2026: From $141
    09

    Mon

  • RIC–MDW, 11/10/2026: From $131
    10

    Tue

  • RIC–MDW: cmp-view-offers-disclaimer. Find Offers
    11

    Wed

  • RIC–MDW, 11/12/2026: From $141
    12

    Thu

  • RIC–MDW, 11/13/2026: From $141
    13

    Fri

  • RIC–MDW: cmp-view-offers-disclaimer. Find Offers
    14

    Sat

  • RIC–MDW, 11/15/2026: From $265
    15

    Sun

  • RIC–MDW, 11/16/2026: From $160
    16

    Mon

  • RIC–MDW: cmp-view-offers-disclaimer. Find Offers
    17

    Tue

  • RIC–MDW, 11/18/2026: From $131
    18

    Wed

  • RIC–MDW, 11/19/2026: From $131
    19

    Thu

  • RIC–MDW: cmp-view-offers-disclaimer. Find Offers
    20

    Fri

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

    Sat

    • Range$131-$344

    *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:
    Chicago Midway International Airport
    Average flight time:
    1 hour 59 minutes
    Distance:
    629 miles

    Questions we hear the most

    The average flight time from Richmond to Chicago (Midway) is 1 hour 59 minutes.
    There are 84 weekly flights from Richmond to Chicago (Midway) on Southwest Airlines.
    Yes, Southwest flies nonstop from Richmond to Chicago (Midway) once per day from Monday through Friday.
    Yes, Southwest flies nonstop from Richmond 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 Richmond 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 Richmond 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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