Southwest® flights from Richmond to Chicago-Midway from $161

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Low fares from Richmond to Chicago-Midway

$

Richmond (RIC)to

Chicago-Midway (MDW)
Depart: 10/03/2026

One-way

Basic

From
$161
Seen: 17 hrs ago

Richmond (RIC)to

Chicago-Midway (MDW)
Depart: 10/26/2026

One-way

Basic

From
$161
Seen: 22 hrs ago

Richmond (RIC)to

Chicago-Midway (MDW)
Depart: 10/22/2026

One-way

Basic

From
$161
Seen: 22 hrs ago

Richmond (RIC)to

Chicago-Midway (MDW)
Depart: 10/17/2026

One-way

Basic

From
$161
Seen: 5 hrs ago

Richmond (RIC)to

Chicago-Midway (MDW)
Depart: 10/06/2026

One-way

Basic

From
$161
Seen: 6 hrs ago

Richmond (RIC)to

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

One-way

Basic

From
$161
Seen: 4 hrs ago

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Explore flights from Richmond to Chicago-Midway

Sep 2026
From$237*
Seen: 13 hrs ago
One Way/Basic
Oct 2026
From$161*
Seen: 4 hrs ago
One Way/Basic
Nov 2026
From$161*
Seen: 9 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $161
cmp-daily-histogram-bars-legend-max-price-aria-label $300
Displaying fares for September-2026
  • RIC–MDW, 09/11/2026: From $254
    11

    Fri

    SEP

  • RIC–MDW, 09/12/2026: From $257
    12

    Sat

  • RIC–MDW, 09/13/2026: From $254
    13

    Sun

  • RIC–MDW, 09/14/2026: From $254
    14

    Mon

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

    Tue

  • RIC–MDW, 09/16/2026: From $247
    16

    Wed

  • RIC–MDW, 09/17/2026: From $254
    17

    Thu

  • RIC–MDW, 09/18/2026: From $300
    18

    Fri

  • RIC–MDW, 09/19/2026: From $237
    19

    Sat

  • RIC–MDW, 09/20/2026: From $254
    20

    Sun

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

    Mon

  • RIC–MDW: cmp-view-offers-disclaimer. Find Offers
    22

    Tue

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

    Wed

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

    Thu

  • RIC–MDW, 09/25/2026: From $258
    25

    Fri

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

    Sat

  • RIC–MDW, 09/27/2026: From $248
    27

    Sun

  • RIC–MDW: cmp-view-offers-disclaimer. Find Offers
    28

    Mon

  • RIC–MDW, 09/29/2026: From $237
    29

    Tue

  • RIC–MDW, 09/30/2026: From $237
    30

    Wed

  • RIC–MDW, 10/01/2026: From $258
    01

    Thu

    OCT

  • RIC–MDW, 10/02/2026: From $172
    02

    Fri

  • RIC–MDW, 10/03/2026: From $161
    03

    Sat

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

    Sun

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

    Mon

  • RIC–MDW, 10/06/2026: From $161
    06

    Tue

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    07

    Wed

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

    Thu

  • RIC–MDW, 10/09/2026: From $172
    09

    Fri

  • RIC–MDW, 10/10/2026: From $161
    10

    Sat

    • Range$161-$300

    *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

    Route Information

    84† Weekly flights
    • 1‡ Nonstop flight 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 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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