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: 10/22/2026

One-way

Basic

From
$109
Seen: 21 hrs ago

Detroit (DTW)to

Chicago (Midway) (MDW)
Depart: 09/26/2026

One-way

Basic

From
$109
Seen: 10 hrs ago

Detroit (DTW)to

Chicago (Midway) (MDW)
Depart: 10/07/2026

One-way

Basic

From
$109
Seen: 15 hrs ago

Detroit (DTW)to

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

One-way

Basic

From
$109
Seen: 22 hrs ago

Detroit (DTW)to

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

One-way

Basic

From
$109
Seen: 6 hrs ago

Detroit (DTW)to

Chicago (Midway) (MDW)
Depart: 11/26/2026

One-way

Basic

From
$109
Seen: 8 hrs ago

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Explore flights from Detroit to Chicago (O'Hare)

Aug 2026
From$209*
Seen: 18 hrs ago
One Way/Basic
Sep 2026
From$109*
Seen: 10 hrs ago
One Way/Basic
Oct 2026
From$109*
Seen: 10 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $109
cmp-daily-histogram-bars-legend-max-price-aria-label $226
Displaying fares for August-2026
  • DTW–MDW, 08/24/2026: From $226
    24

    Mon

    AUG

  • DTW–MDW, 08/25/2026: From $209
    25

    Tue

  • DTW–MDW, 08/26/2026: From $209
    26

    Wed

  • DTW–MDW, 08/27/2026: From $226
    27

    Thu

  • DTW–MDW, 08/28/2026: From $226
    28

    Fri

  • DTW–MDW, 08/29/2026: From $209
    29

    Sat

  • DTW–MDW, 08/30/2026: From $226
    30

    Sun

  • DTW–MDW, 08/31/2026: From $226
    31

    Mon

  • DTW–MDW, 09/01/2026: From $209
    01

    Tue

    SEP

  • DTW–MDW, 09/02/2026: From $209
    02

    Wed

  • DTW–MDW, 09/03/2026: From $226
    03

    Thu

  • DTW–MDW, 09/04/2026: From $226
    04

    Fri

  • DTW–MDW, 09/05/2026: From $157
    05

    Sat

  • DTW–MDW, 09/06/2026: From $157
    06

    Sun

  • DTW–MDW, 09/07/2026: From $226
    07

    Mon

  • DTW–MDW, 09/08/2026: From $209
    08

    Tue

  • DTW–MDW, 09/09/2026: From $157
    09

    Wed

  • DTW–MDW, 09/10/2026: From $157
    10

    Thu

  • DTW–MDW, 09/11/2026: From $157
    11

    Fri

  • DTW–MDW, 09/12/2026: From $157
    12

    Sat

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

    Sun

  • DTW–MDW, 09/14/2026: From $189
    14

    Mon

  • DTW–MDW, 09/15/2026: From $109
    15

    Tue

  • DTW–MDW, 09/16/2026: From $109
    16

    Wed

  • DTW–MDW, 09/17/2026: From $109
    17

    Thu

  • DTW–MDW, 09/18/2026: From $125
    18

    Fri

  • DTW–MDW, 09/19/2026: From $109
    19

    Sat

  • DTW–MDW: cmp-view-offers-disclaimer. Find Offers
    20

    Sun

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

    Mon

  • DTW–MDW, 09/22/2026: From $109
    22

    Tue

  • DTW–MDW, 09/23/2026: From $109
    23

    Wed

    • Range$109-$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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