Southwest® flights from Chicago-Midway to Boston from $154

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Low fares from Chicago-Midway to Boston

$

Chicago-Midway (MDW)to

Boston (BOS)
Depart: 11/23/2026

One-way

Basic

From
$154
Seen: 20 hrs ago

Chicago-Midway (MDW)to

Boston (BOS)
Depart: 11/22/2026

One-way

Basic

From
$154
Seen: 20 hrs ago

Chicago-Midway (MDW)to

Boston (BOS)
Depart: 11/19/2026

One-way

Basic

From
$164
Seen: 1 hour ago

Chicago-Midway (MDW)to

Boston (BOS)
Depart: 11/21/2026

One-way

Basic

From
$169
Seen: 6 hrs ago

Chicago-Midway (MDW)to

Boston (BOS)
Depart: 11/10/2026

One-way

Basic

From
$178
Seen: 21 hrs ago

Chicago-Midway (MDW)to

Boston (BOS)
Depart: 11/17/2026

One-way

Basic

From
$178
Seen: 21 hrs ago

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Explore flights from Chicago-Midway to Boston

Oct 2026
From$219*
Seen: 20 minutes ago
One Way/Basic
Nov 2026
From$154*
Seen: 20 hrs ago
One Way/Basic
Dec 2026
From$178*
Seen: 3 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $154
cmp-daily-histogram-bars-legend-max-price-aria-label $433
Displaying fares for October-2026
  • MDW–BOS, 10/26/2026: From $219
    26

    Mon

    OCT

  • MDW–BOS, 10/27/2026: From $219
    27

    Tue

  • MDW–BOS, 10/28/2026: From $219
    28

    Wed

  • MDW–BOS, 10/29/2026: From $219
    29

    Thu

  • MDW–BOS, 10/30/2026: From $319
    30

    Fri

  • MDW–BOS, 10/31/2026: From $219
    31

    Sat

  • MDW–BOS, 11/01/2026: From $219
    01

    Sun

    NOV

  • MDW–BOS, 11/02/2026: From $219
    02

    Mon

  • MDW–BOS, 11/03/2026: From $219
    03

    Tue

  • MDW–BOS, 11/04/2026: From $219
    04

    Wed

  • MDW–BOS, 11/05/2026: From $219
    05

    Thu

  • MDW–BOS, 11/06/2026: From $219
    06

    Fri

  • MDW–BOS, 11/07/2026: From $178
    07

    Sat

  • MDW–BOS: cmp-view-offers-disclaimer. Find Offers
    08

    Sun

  • MDW–BOS, 11/09/2026: From $178
    09

    Mon

  • MDW–BOS, 11/10/2026: From $178
    10

    Tue

  • MDW–BOS, 11/11/2026: From $178
    11

    Wed

  • MDW–BOS, 11/12/2026: From $178
    12

    Thu

  • MDW–BOS, 11/13/2026: From $178
    13

    Fri

  • MDW–BOS, 11/14/2026: From $178
    14

    Sat

  • MDW–BOS, 11/15/2026: From $433
    15

    Sun

  • MDW–BOS, 11/16/2026: From $178
    16

    Mon

  • MDW–BOS, 11/17/2026: From $178
    17

    Tue

  • MDW–BOS, 11/18/2026: From $178
    18

    Wed

  • MDW–BOS, 11/19/2026: From $164
    19

    Thu

  • MDW–BOS, 11/20/2026: From $178
    20

    Fri

  • MDW–BOS, 11/21/2026: From $169
    21

    Sat

  • MDW–BOS, 11/22/2026: From $154
    22

    Sun

  • MDW–BOS, 11/23/2026: From $154
    23

    Mon

  • MDW–BOS, 11/24/2026: From $178
    24

    Tue

  • MDW–BOS, 11/25/2026: From $178
    25

    Wed

    • Range$154-$433

    *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:
    Logan International Airport
    Average flight time:
    2 hours 16 minutes
    Distance:
    861 miles

    Questions we hear the most

    The average flight time from Chicago (Midway) to Boston is 2 hours 16 minutes.
    There are 147 weekly flights from Chicago (Midway) to Boston on Southwest Airlines.
    Yes, Southwest flies nonstop from Chicago (Midway) to Boston 4 times per day from Monday through Friday.
    Yes, Southwest flies nonstop from Chicago (Midway) to Boston 4 times per day on Saturdays and 5 times per day on Sundays.
    To find the lowest fares by day and time to fly Chicago (Midway) 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 Chicago (Midway) 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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