Southwest® flights from Milwaukee to Boston from $176

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Low fares from Milwaukee to Boston

$

Milwaukee (MKE)to

Boston (BOS)
Depart: 11/06/2026

One-way

Basic

From
$176
Seen: 22 hrs ago

Milwaukee (MKE)to

Boston (BOS)
Depart: 11/05/2026

One-way

Basic

From
$186
Seen: 14 hrs ago

Milwaukee (MKE)to

Boston (BOS)
Depart: 10/24/2026

One-way

Basic

From
$189
Seen: 19 hrs ago

Milwaukee (MKE)to

Boston (BOS)
Depart: 10/28/2026

One-way

Basic

From
$189
Seen: 12 hrs ago

Milwaukee (MKE)to

Boston (BOS)
Depart: 12/17/2026

One-way

Basic

From
$189
Seen: 9 hrs ago

Milwaukee (MKE)to

Boston (BOS)
Depart: 11/16/2026

One-way

Basic

From
$189
Seen: 7 hrs ago

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Explore flights from Milwaukee to Boston

Oct 2026
From$189*
Seen: 19 hrs ago
One Way/Basic
Nov 2026
From$176*
Seen: 22 hrs ago
One Way/Basic
Dec 2026
From$189*
Seen: 9 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $189
cmp-daily-histogram-bars-legend-max-price-aria-label $469
Displaying fares for October-2026
  • MKE–BOS, 10/02/2026: From $469
    02

    Fri

    OCT

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

    Sat

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    04

    Sun

  • MKE–BOS, 10/05/2026: From $419
    05

    Mon

  • MKE–BOS, 10/06/2026: From $419
    06

    Tue

  • MKE–BOS, 10/07/2026: From $253
    07

    Wed

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    08

    Thu

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    09

    Fri

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    10

    Sat

  • MKE–BOS, 10/11/2026: From $309
    11

    Sun

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    12

    Mon

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    13

    Tue

  • MKE–BOS, 10/14/2026: From $253
    14

    Wed

  • MKE–BOS, 10/15/2026: From $253
    15

    Thu

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

    Fri

  • MKE–BOS, 10/17/2026: From $204
    17

    Sat

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

    Sun

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    19

    Mon

  • MKE–BOS, 10/20/2026: From $253
    20

    Tue

  • MKE–BOS, 10/21/2026: From $219
    21

    Wed

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

    Thu

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    23

    Fri

  • MKE–BOS, 10/24/2026: From $189
    24

    Sat

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

    Sun

  • MKE–BOS: cmp-view-offers-disclaimer. Find Offers
    26

    Mon

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

    Tue

  • MKE–BOS, 10/28/2026: From $189
    28

    Wed

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    29

    Thu

  • MKE–BOS, 10/30/2026: From $203
    30

    Fri

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    31

    Sat

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

    Sun

    NOV

    • Range$189-$469

    *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:
    Logan International 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 Milwaukee to Boston on Southwest Airlines.
    To find the lowest fares by day and time to fly Milwaukee to Boston with Southwest, check out our Low Fare Calendar.
    You can rent a car at Logan International Airport book yours with your flight.
    Yes! Flights from Milwaukee to Boston—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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