Southwest® flights from Washington, D.C. (Reagan National) to Chicago (O'Hare)

Promo Code

Low fares from Washington, D.C. (Reagan National) to Chicago (O'Hare)

$

Washington, D.C. (Reagan National) (DCA)to

Chicago (Midway) (MDW)
Depart: 09/16/2026

One-way

Basic

From
$89
Seen: 12 hrs ago

Washington, D.C. (Reagan National) (DCA)to

Chicago (Midway) (MDW)
Depart: 12/02/2026

One-way

Basic

From
$89
Seen: 8 hrs ago

Washington, D.C. (Reagan National) (DCA)to

Chicago (Midway) (MDW)
Depart: 09/22/2026

One-way

Basic

From
$89
Seen: 22 hrs ago

Washington, D.C. (Reagan National) (DCA)to

Chicago (Midway) (MDW)
Depart: 09/30/2026

One-way

Basic

From
$89
Seen: 22 hrs ago

Washington, D.C. (Reagan National) (DCA)to

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

One-way

Basic

From
$89
Seen: 18 hrs ago

Washington, D.C. (Reagan National) (DCA)to

Chicago (Midway) (MDW)
Depart: 10/13/2026

One-way

Basic

From
$89
Seen: 6 hrs ago

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Explore flights from Washington, D.C. (Reagan National) to Chicago (O'Hare)

Aug 2026
From$237*
Seen: 22 hrs ago
One Way/Basic
Sep 2026
From$89*
Seen: 22 hrs ago
One Way/Basic
Oct 2026
From$89*
Seen: 8 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $89
cmp-daily-histogram-bars-legend-max-price-aria-label $237
Displaying fares for August-2026
  • DCA–MDW, 08/25/2026: From $237
    25

    Tue

    AUG

  • DCA–MDW, 08/26/2026: From $237
    26

    Wed

  • DCA–MDW, 08/27/2026: From $237
    27

    Thu

  • DCA–MDW, 08/28/2026: From $237
    28

    Fri

  • DCA–MDW, 08/29/2026: From $237
    29

    Sat

  • DCA–MDW: cmp-view-offers-disclaimer. Find Offers
    30

    Sun

  • DCA–MDW, 08/31/2026: From $237
    31

    Mon

  • DCA–MDW, 09/01/2026: From $237
    01

    Tue

    SEP

  • DCA–MDW, 09/02/2026: From $237
    02

    Wed

  • DCA–MDW, 09/03/2026: From $237
    03

    Thu

  • DCA–MDW, 09/04/2026: From $237
    04

    Fri

  • DCA–MDW, 09/05/2026: From $183
    05

    Sat

  • DCA–MDW, 09/06/2026: From $183
    06

    Sun

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

    Mon

  • DCA–MDW, 09/08/2026: From $227
    08

    Tue

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

    Wed

  • DCA–MDW, 09/10/2026: From $183
    10

    Thu

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

    Fri

  • DCA–MDW, 09/12/2026: From $183
    12

    Sat

  • DCA–MDW, 09/13/2026: From $227
    13

    Sun

  • DCA–MDW, 09/14/2026: From $89
    14

    Mon

  • DCA–MDW, 09/15/2026: From $89
    15

    Tue

  • DCA–MDW, 09/16/2026: From $89
    16

    Wed

  • DCA–MDW, 09/17/2026: From $99
    17

    Thu

  • DCA–MDW, 09/18/2026: From $128
    18

    Fri

  • DCA–MDW, 09/19/2026: From $89
    19

    Sat

  • DCA–MDW, 09/20/2026: From $190
    20

    Sun

  • DCA–MDW, 09/21/2026: From $89
    21

    Mon

  • DCA–MDW, 09/22/2026: From $89
    22

    Tue

  • DCA–MDW, 09/23/2026: From $89
    23

    Wed

  • DCA–MDW, 09/24/2026: From $154
    24

    Thu

    • Range$89-$237

    *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:
    Ronald Reagan National Airport
    Arriving at:
    O'Hare International Airport
    Distance:
    612 miles

    Route Information

    64† 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 64 weekly flights from Washington, D.C. (Reagan National) to Chicago (O'Hare) on Southwest Airlines.
    To find the lowest fares by day and time to fly Washington, D.C. (Reagan National) 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 Washington, D.C. (Reagan National) 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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