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

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Low fares from Chicago (Midway) to Milwaukee

$

Chicago (Midway) (MDW)to

Milwaukee (MKE)
Depart: 09/05/2026

One-way

Basic

From
$90
Seen: 14 hrs ago

Chicago (Midway) (MDW)to

Milwaukee (MKE)
Depart: 09/06/2026

One-way

Basic

From
$90
Seen: 13 hrs ago

Chicago (Midway) (MDW)to

Milwaukee (MKE)
Depart: 09/11/2026

One-way

Basic

From
$90
Seen: 15 hrs ago

Chicago (Midway) (MDW)to

Milwaukee (MKE)
Depart: 09/24/2026

One-way

Basic

From
$100
Seen: 19 hrs ago

Chicago (Midway) (MDW)to

Milwaukee (MKE)
Depart: 08/24/2026

One-way

Basic

From
$100
Seen: 16 hrs ago

Chicago (Midway) (MDW)to

Milwaukee (MKE)
Depart: 09/07/2026

One-way

Basic

From
$100
Seen: 10 hrs ago

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Explore flights from Chicago (Midway) to Milwaukee

Aug 2026
From$100*
Seen: 16 hrs ago
One Way/Basic
Sep 2026
From$90*
Seen: 15 hrs ago
One Way/Basic
Oct 2026
From$100*
Seen: 16 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $100
cmp-daily-histogram-bars-legend-max-price-aria-label $242
Displaying fares for August-2026
  • MDW–MKE: cmp-view-offers-disclaimer. Find Offers
    05

    Wed

    AUG

  • MDW–MKE, 08/06/2026: From $242
    06

    Thu

  • MDW–MKE, 08/07/2026: From $242
    07

    Fri

  • MDW–MKE, 08/08/2026: From $195
    08

    Sat

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

    Sun

  • MDW–MKE: cmp-view-offers-disclaimer. Find Offers
    10

    Mon

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

    Tue

  • MDW–MKE, 08/12/2026: From $240
    12

    Wed

  • MDW–MKE, 08/13/2026: From $240
    13

    Thu

  • MDW–MKE, 08/14/2026: From $240
    14

    Fri

  • MDW–MKE: cmp-view-offers-disclaimer. Find Offers
    15

    Sat

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

    Sun

  • MDW–MKE, 08/17/2026: From $240
    17

    Mon

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

    Tue

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

    Wed

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

    Thu

  • MDW–MKE, 08/21/2026: From $144
    21

    Fri

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

    Sat

  • MDW–MKE, 08/23/2026: From $154
    23

    Sun

  • MDW–MKE, 08/24/2026: From $100
    24

    Mon

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

    Tue

  • MDW–MKE, 08/26/2026: From $100
    26

    Wed

  • MDW–MKE, 08/27/2026: From $100
    27

    Thu

  • MDW–MKE, 08/28/2026: From $108
    28

    Fri

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

    Sat

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

    Sun

  • MDW–MKE: cmp-view-offers-disclaimer. Find Offers
    31

    Mon

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

    Tue

    SEP

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

    Wed

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

    Thu

  • MDW–MKE, 09/04/2026: From $115
    04

    Fri

    • Range$100-$242

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

    Route Information

    14† 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 14 weekly flights from Chicago (Midway) to Milwaukee on Southwest Airlines.
    To find the lowest fares by day and time to fly Chicago (Midway) to Milwaukee with Southwest, check out our Low Fare Calendar.
    You can rent a car at General Mitchell Airport book yours with your flight.
    Yes! Flights from Chicago (Midway) to Milwaukee—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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