Southwest® flights from Chicago (Midway) to Boston from $104

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Low fares from Chicago (Midway) to Boston

$

Chicago (Midway) (MDW)to

Boston (BOS)
Depart: 09/15/2026

One-way

Basic

From
$104
Seen: 25 minutes ago

Chicago (Midway) (MDW)to

Boston (BOS)
Depart: 10/20/2026

One-way

Basic

From
$109
Seen: 23 hrs ago

Chicago (Midway) (MDW)to

Boston (BOS)
Depart: 10/03/2026

One-way

Basic

From
$109
Seen: 14 hrs ago

Chicago (Midway) (MDW)to

Boston (BOS)
Depart: 11/04/2026

One-way

Basic

From
$109
Seen: 8 hrs ago

Chicago (Midway) (MDW)to

Boston (BOS)
Depart: 09/29/2026

One-way

Basic

From
$109
Seen: 20 hrs ago

Chicago (Midway) (MDW)to

Boston (BOS)
Depart: 10/07/2026

One-way

Basic

From
$109
Seen: 22 hrs ago

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Explore flights from Chicago (Midway) to Boston

Aug 2026
From$123*
Seen: 13 hrs ago
One Way/Basic
Sep 2026
From$104*
Seen: 25 minutes ago
One Way/Basic
Oct 2026
From$109*
Seen: 2 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $123
cmp-daily-histogram-bars-legend-max-price-aria-label $189
Displaying fares for August-2026
  • MDW–BOS, 08/04/2026: From $189
    04

    Tue

    AUG

  • MDW–BOS, 08/05/2026: From $179
    05

    Wed

  • MDW–BOS, 08/06/2026: From $159
    06

    Thu

  • MDW–BOS, 08/07/2026: From $154
    07

    Fri

  • MDW–BOS, 08/08/2026: From $154
    08

    Sat

  • MDW–BOS, 08/09/2026: From $159
    09

    Sun

  • MDW–BOS, 08/10/2026: From $154
    10

    Mon

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

    Tue

  • MDW–BOS, 08/12/2026: From $154
    12

    Wed

  • MDW–BOS, 08/13/2026: From $154
    13

    Thu

  • MDW–BOS, 08/14/2026: From $154
    14

    Fri

  • MDW–BOS, 08/15/2026: From $154
    15

    Sat

  • MDW–BOS, 08/16/2026: From $154
    16

    Sun

  • MDW–BOS, 08/17/2026: From $123
    17

    Mon

  • MDW–BOS, 08/18/2026: From $128
    18

    Tue

  • MDW–BOS, 08/19/2026: From $128
    19

    Wed

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

    Thu

  • MDW–BOS, 08/21/2026: From $164
    21

    Fri

  • MDW–BOS, 08/22/2026: From $123
    22

    Sat

  • MDW–BOS, 08/23/2026: From $123
    23

    Sun

  • MDW–BOS, 08/24/2026: From $128
    24

    Mon

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

    Tue

  • MDW–BOS, 08/26/2026: From $128
    26

    Wed

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

    Thu

  • MDW–BOS, 08/28/2026: From $123
    28

    Fri

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

    Sat

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

    Sun

  • MDW–BOS, 08/31/2026: From $123
    31

    Mon

  • MDW–BOS, 09/01/2026: From $123
    01

    Tue

    SEP

  • MDW–BOS, 09/02/2026: From $123
    02

    Wed

  • MDW–BOS, 09/03/2026: From $163
    03

    Thu

    • Range$123-$189

    *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

    Route Information

    147† Weekly flights
    • 4‡ Nonstop flights per day Monday through Friday
    • 4‡ Nonstop flights on Saturday
    • 5‡ Nonstop flights on Sunday

    † 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

    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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