Southwest® flights from Boston to Milwaukee from $159

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Low fares from Boston to Milwaukee

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Boston (BOS)to

Milwaukee (MKE)
Depart: 11/18/2026

One-way

Basic

From
$159
Seen: 7 hrs ago

Boston (BOS)to

Milwaukee (MKE)
Depart: 10/20/2026

One-way

Basic

From
$159
Seen: 11 hrs ago

Boston (BOS)to

Milwaukee (MKE)
Depart: 09/23/2026

One-way

Basic

From
$159
Seen: 2 hrs ago

Boston (BOS)to

Milwaukee (MKE)
Depart: 10/07/2026

One-way

Basic

From
$159
Seen: 5 hrs ago

Boston (BOS)to

Milwaukee (MKE)
Depart: 10/02/2026

One-way

Basic

From
$184
Seen: 14 hrs ago

Boston (BOS)to

Milwaukee (MKE)
Depart: 10/17/2026

One-way

Basic

From
$184
Seen: 15 hrs ago

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Explore flights from Boston to Milwaukee

Sep 2026
From$159*
Seen: 2 hrs ago
One Way/Basic
Oct 2026
From$159*
Seen: 11 hrs ago
One Way/Basic
Nov 2026
From$159*
Seen: 7 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $159
cmp-daily-histogram-bars-legend-max-price-aria-label $459
Displaying fares for September-2026
  • BOS–MKE, 09/11/2026: From $459
    11

    Fri

    SEP

  • BOS–MKE, 09/12/2026: From $409
    12

    Sat

  • BOS–MKE, 09/13/2026: From $409
    13

    Sun

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

    Mon

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

    Tue

  • BOS–MKE, 09/16/2026: From $289
    16

    Wed

  • BOS–MKE, 09/17/2026: From $289
    17

    Thu

  • BOS–MKE, 09/18/2026: From $289
    18

    Fri

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

    Sat

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

    Sun

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

    Mon

  • BOS–MKE, 09/22/2026: From $289
    22

    Tue

  • BOS–MKE, 09/23/2026: From $159
    23

    Wed

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

    Thu

  • BOS–MKE, 09/25/2026: From $184
    25

    Fri

  • BOS–MKE, 09/26/2026: From $184
    26

    Sat

  • BOS–MKE: cmp-view-offers-disclaimer. Find Offers
    27

    Sun

  • BOS–MKE: cmp-view-offers-disclaimer. Find Offers
    28

    Mon

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

    Tue

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

    Wed

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

    Thu

    OCT

  • BOS–MKE, 10/02/2026: From $184
    02

    Fri

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

    Sat

  • BOS–MKE, 10/04/2026: From $259
    04

    Sun

  • BOS–MKE: cmp-view-offers-disclaimer. Find Offers
    05

    Mon

  • BOS–MKE: cmp-view-offers-disclaimer. Find Offers
    06

    Tue

  • BOS–MKE, 10/07/2026: From $159
    07

    Wed

  • BOS–MKE, 10/08/2026: From $209
    08

    Thu

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

    Fri

  • BOS–MKE, 10/10/2026: From $234
    10

    Sat

    • Range$159-$459

    *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:
    Logan International Airport
    Arriving at:
    General Mitchell Airport
    Distance:
    860 miles

    Route Information

    116† 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 116 weekly flights from Boston to Milwaukee on Southwest Airlines.
    To find the lowest fares by day and time to fly Boston 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 Boston 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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