Southwest® flights from Detroit to Chicago (O'Hare)

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Low fares from Detroit to Chicago (O'Hare)

$

Detroit (DTW)to

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

One-way

Basic

From
$109
Seen: 16 hrs ago

Detroit (DTW)to

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

One-way

Basic

From
$109
Seen: 11 hrs ago

Detroit (DTW)to

Chicago (Midway) (MDW)
Depart: 09/17/2026

One-way

Basic

From
$125
Seen: 23 hrs ago

Detroit (DTW)to

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

One-way

Basic

From
$125
Seen: 19 hrs ago

Detroit (DTW)to

Chicago (Midway) (MDW)
Depart: 09/03/2026

One-way

Basic

From
$125
Seen: 7 hrs ago

Detroit (DTW)to

Chicago (Midway) (MDW)
Depart: 08/27/2026

One-way

Basic

From
$125
Seen: 13 hrs ago

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Explore flights from Detroit to Chicago (O'Hare)

Aug 2026
From$125*
Seen: 13 hrs ago
One Way/Basic
Sep 2026
From$109*
Seen: 11 hrs ago
One Way/Basic
Oct 2026
From$109*
Seen: 16 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $125
cmp-daily-histogram-bars-legend-max-price-aria-label $226
Displaying fares for August-2026
  • DTW–MDW, 08/05/2026: From $224
    05

    Wed

    AUG

  • DTW–MDW, 08/06/2026: From $226
    06

    Thu

  • DTW–MDW, 08/07/2026: From $226
    07

    Fri

  • DTW–MDW, 08/08/2026: From $209
    08

    Sat

  • DTW–MDW, 08/09/2026: From $226
    09

    Sun

  • DTW–MDW, 08/10/2026: From $226
    10

    Mon

  • DTW–MDW, 08/11/2026: From $217
    11

    Tue

  • DTW–MDW, 08/12/2026: From $209
    12

    Wed

  • DTW–MDW, 08/13/2026: From $226
    13

    Thu

  • DTW–MDW, 08/14/2026: From $226
    14

    Fri

  • DTW–MDW, 08/15/2026: From $209
    15

    Sat

  • DTW–MDW, 08/16/2026: From $226
    16

    Sun

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

    Mon

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

    Tue

  • DTW–MDW, 08/19/2026: From $209
    19

    Wed

  • DTW–MDW, 08/20/2026: From $226
    20

    Thu

  • DTW–MDW, 08/21/2026: From $226
    21

    Fri

  • DTW–MDW, 08/22/2026: From $209
    22

    Sat

  • DTW–MDW, 08/23/2026: From $226
    23

    Sun

  • DTW–MDW, 08/24/2026: From $226
    24

    Mon

  • DTW–MDW, 08/25/2026: From $125
    25

    Tue

  • DTW–MDW, 08/26/2026: From $125
    26

    Wed

  • DTW–MDW, 08/27/2026: From $125
    27

    Thu

  • DTW–MDW, 08/28/2026: From $144
    28

    Fri

  • DTW–MDW: cmp-view-offers-disclaimer. Find Offers
    29

    Sat

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

    Sun

  • DTW–MDW, 08/31/2026: From $125
    31

    Mon

  • DTW–MDW, 09/01/2026: From $125
    01

    Tue

    SEP

  • DTW–MDW, 09/02/2026: From $125
    02

    Wed

  • DTW–MDW, 09/03/2026: From $125
    03

    Thu

  • DTW–MDW, 09/04/2026: From $144
    04

    Fri

    • Range$125-$226

    *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:
    Wayne County Airport
    Arriving at:
    O'Hare International Airport
    Distance:
    235 miles

    Route Information

    9† 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 9 weekly flights from Detroit to Chicago (O'Hare) on Southwest Airlines.
    To find the lowest fares by day and time to fly Detroit 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 Detroit 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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