Southwest® flights from Milwaukee to Chicago (Midway) from $90

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Low fares from Milwaukee to Chicago (Midway)

$

Milwaukee (MKE)to

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

One-way

Basic

From
$90
Seen: 10 hrs ago

Milwaukee (MKE)to

Chicago (Midway) (MDW)
Depart: 09/15/2026

One-way

Basic

From
$90
Seen: 7 hrs ago

Milwaukee (MKE)to

Chicago (Midway) (MDW)
Depart: 09/23/2026

One-way

Basic

From
$90
Seen: 8 hrs ago

Milwaukee (MKE)to

Chicago (Midway) (MDW)
Depart: 09/19/2026

One-way

Basic

From
$90
Seen: 9 hrs ago

Milwaukee (MKE)to

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

One-way

Basic

From
$90
Seen: 6 hrs ago

Milwaukee (MKE)to

Chicago (Midway) (MDW)
Depart: 10/15/2026

One-way

Basic

From
$90
Seen: 22 hrs ago

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Explore flights from Milwaukee to Chicago (Midway)

Aug 2026
From$240*
Seen: 16 hrs ago
One Way/Basic
Sep 2026
From$90*
Seen: 9 hrs ago
One Way/Basic
Oct 2026
From$90*
Seen: 22 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $90
cmp-daily-histogram-bars-legend-max-price-aria-label $240
Displaying fares for August-2026
  • MKE–MDW, 08/25/2026: From $240
    25

    Tue

    AUG

  • MKE–MDW, 08/26/2026: From $240
    26

    Wed

  • MKE–MDW, 08/27/2026: From $240
    27

    Thu

  • MKE–MDW, 08/28/2026: From $240
    28

    Fri

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

    Sat

  • MKE–MDW, 08/30/2026: From $240
    30

    Sun

  • MKE–MDW, 08/31/2026: From $240
    31

    Mon

  • MKE–MDW: cmp-view-offers-disclaimer. Find Offers
    01

    Tue

    SEP

  • MKE–MDW: cmp-view-offers-disclaimer. Find Offers
    02

    Wed

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

    Thu

  • MKE–MDW, 09/04/2026: From $240
    04

    Fri

  • MKE–MDW, 09/05/2026: From $160
    05

    Sat

  • MKE–MDW, 09/06/2026: From $160
    06

    Sun

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

    Mon

  • MKE–MDW, 09/08/2026: From $144
    08

    Tue

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

    Wed

  • MKE–MDW, 09/10/2026: From $144
    10

    Thu

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

    Fri

  • MKE–MDW: cmp-view-offers-disclaimer. Find Offers
    12

    Sat

  • MKE–MDW, 09/13/2026: From $144
    13

    Sun

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

    Mon

  • MKE–MDW, 09/15/2026: From $90
    15

    Tue

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

    Wed

  • MKE–MDW, 09/17/2026: From $90
    17

    Thu

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

    Fri

  • MKE–MDW, 09/19/2026: From $90
    19

    Sat

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

    Sun

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

    Mon

  • MKE–MDW, 09/22/2026: From $90
    22

    Tue

  • MKE–MDW, 09/23/2026: From $90
    23

    Wed

  • MKE–MDW: cmp-view-offers-disclaimer. Find Offers
    24

    Thu

    • Range$90-$240

    *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:
    General Mitchell Airport
    Arriving at:
    Chicago Midway International Airport
    Distance:
    80 miles

    Route Information

    6† 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 6 weekly flights from Milwaukee to Chicago (Midway) on Southwest Airlines.
    To find the lowest fares by day and time to fly Milwaukee 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 Milwaukee 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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