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: 09/05/2026

One-way

Basic

From
$89
Seen: 2 hrs ago

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

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

One-way

Basic

From
$89
Seen: 1 hour ago

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

Chicago (Midway) (MDW)
Depart: 09/06/2026

One-way

Basic

From
$89
Seen: 14 hrs ago

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

Chicago (Midway) (MDW)
Depart: 10/30/2026

One-way

Basic

From
$89
Seen: 19 hrs ago

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

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

One-way

Basic

From
$105
Seen: 9 hrs ago

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

Chicago (Midway) (MDW)
Depart: 10/24/2026

One-way

Basic

From
$128
Seen: 20 hrs ago

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

Aug 2026
From$128*
Seen: 2 hrs ago
One Way/Basic
Sep 2026
From$89*
Seen: 14 hrs ago
One Way/Basic
Oct 2026
From$89*
Seen: 19 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $128
cmp-daily-histogram-bars-legend-max-price-aria-label $261
Displaying fares for August-2026
  • DCA–MDW, 08/04/2026: From $229
    04

    Tue

    AUG

  • DCA–MDW, 08/05/2026: From $229
    05

    Wed

  • DCA–MDW, 08/06/2026: From $261
    06

    Thu

  • DCA–MDW, 08/07/2026: From $261
    07

    Fri

  • DCA–MDW, 08/08/2026: From $229
    08

    Sat

  • DCA–MDW, 08/09/2026: From $261
    09

    Sun

  • DCA–MDW, 08/10/2026: From $261
    10

    Mon

  • DCA–MDW, 08/11/2026: From $229
    11

    Tue

  • DCA–MDW, 08/12/2026: From $229
    12

    Wed

  • DCA–MDW: cmp-view-offers-disclaimer. Find Offers
    13

    Thu

  • DCA–MDW, 08/14/2026: From $261
    14

    Fri

  • DCA–MDW, 08/15/2026: From $229
    15

    Sat

  • DCA–MDW, 08/16/2026: From $261
    16

    Sun

  • DCA–MDW, 08/17/2026: From $227
    17

    Mon

  • DCA–MDW: cmp-view-offers-disclaimer. Find Offers
    18

    Tue

  • DCA–MDW: cmp-view-offers-disclaimer. Find Offers
    19

    Wed

  • DCA–MDW, 08/20/2026: From $227
    20

    Thu

  • DCA–MDW, 08/21/2026: From $227
    21

    Fri

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

    Sat

  • DCA–MDW, 08/23/2026: From $227
    23

    Sun

  • DCA–MDW, 08/24/2026: From $128
    24

    Mon

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

    Tue

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

    Wed

  • DCA–MDW, 08/27/2026: From $128
    27

    Thu

  • DCA–MDW, 08/28/2026: From $157
    28

    Fri

  • DCA–MDW, 08/29/2026: From $128
    29

    Sat

  • DCA–MDW, 08/30/2026: From $190
    30

    Sun

  • DCA–MDW, 08/31/2026: From $128
    31

    Mon

  • DCA–MDW, 09/01/2026: From $128
    01

    Tue

    SEP

  • DCA–MDW, 09/02/2026: From $128
    02

    Wed

  • DCA–MDW, 09/03/2026: From $154
    03

    Thu

    • Range$128-$261

    *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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