Southwest® flights from Richmond to Chicago-Midway from $165

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Low fares from Richmond to Chicago-Midway

$

Richmond (RIC)to

Chicago-Midway (MDW)
Depart: 01/09/2027

One-way

Basic

From
$165
Seen: 13 hrs ago

Richmond (RIC)to

Chicago-Midway (MDW)
Depart: 01/12/2027

One-way

Basic

From
$165
Seen: 19 hrs ago

Richmond (RIC)to

Chicago-Midway (MDW)
Depart: 01/27/2027

One-way

Basic

From
$165
Seen: 10 hrs ago

Richmond (RIC)to

Chicago-Midway (MDW)
Depart: 01/26/2027

One-way

Basic

From
$165
Seen: 13 hrs ago

Richmond (RIC)to

Chicago-Midway (MDW)
Depart: 02/13/2027

One-way

Basic

From
$165
Seen: 17 hrs ago

Richmond (RIC)to

Chicago-Midway (MDW)
Depart: 01/20/2027

One-way

Basic

From
$165
Seen: 15 hrs ago

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Explore flights from Richmond to Chicago-Midway

Nov 2026
From$226*
Seen: 16 hrs ago
One Way/Basic
Dec 2026
From$175*
Seen: 16 hrs ago
One Way/Basic
Jan 2027
From$165*
Seen: 13 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $175
cmp-daily-histogram-bars-legend-max-price-aria-label $401
Displaying fares for November-2026
  • RIC–MDW: cmp-view-offers-disclaimer. Find Offers
    12

    Thu

    NOV

  • RIC–MDW, 11/13/2026: From $226
    13

    Fri

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

    Sat

  • RIC–MDW, 11/15/2026: From $304
    15

    Sun

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

    Mon

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

    Tue

  • RIC–MDW, 11/18/2026: From $226
    18

    Wed

  • RIC–MDW, 11/19/2026: From $226
    19

    Thu

  • RIC–MDW, 11/20/2026: From $236
    20

    Fri

  • RIC–MDW, 11/21/2026: From $236
    21

    Sat

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

    Sun

  • RIC–MDW, 11/23/2026: From $226
    23

    Mon

  • RIC–MDW, 11/24/2026: From $236
    24

    Tue

  • RIC–MDW, 11/25/2026: From $236
    25

    Wed

  • RIC–MDW, 11/26/2026: From $236
    26

    Thu

  • RIC–MDW, 11/27/2026: From $241
    27

    Fri

  • RIC–MDW, 11/28/2026: From $386
    28

    Sat

  • RIC–MDW, 11/29/2026: From $401
    29

    Sun

  • RIC–MDW, 11/30/2026: From $274
    30

    Mon

  • RIC–MDW, 12/01/2026: From $226
    01

    Tue

    DEC

  • RIC–MDW, 12/02/2026: From $175
    02

    Wed

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

    Thu

  • RIC–MDW, 12/04/2026: From $210
    04

    Fri

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

    Sat

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

    Sun

  • RIC–MDW, 12/07/2026: From $185
    07

    Mon

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

    Tue

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

    Wed

  • RIC–MDW, 12/10/2026: From $185
    10

    Thu

  • RIC–MDW, 12/11/2026: From $210
    11

    Fri

    • Range$175-$401

    *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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