Southwest® flights from Chicago (Midway) to Boston from $109

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Low fares from Chicago (Midway) to Boston

$

Chicago (Midway) (MDW)to

Boston (BOS)
Depart: 10/19/2026

One-way

Basic

From
$109
Seen: 22 hrs ago

Chicago (Midway) (MDW)to

Boston (BOS)
Depart: 10/05/2026

One-way

Basic

From
$109
Seen: 22 hrs ago

Chicago (Midway) (MDW)to

Boston (BOS)
Depart: 11/14/2026

One-way

Basic

From
$109
Seen: 19 hrs ago

Chicago (Midway) (MDW)to

Boston (BOS)
Depart: 10/03/2026

One-way

Basic

From
$109
Seen: 19 hrs ago

Chicago (Midway) (MDW)to

Boston (BOS)
Depart: 11/05/2026

One-way

Basic

From
$109
Seen: 13 hrs ago

Chicago (Midway) (MDW)to

Boston (BOS)
Depart: 11/07/2026

One-way

Basic

From
$109
Seen: 12 hrs ago

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Explore flights from Chicago (Midway) to Boston

Aug 2026
From$169*
Seen: 11 hrs ago
One Way/Basic
Sep 2026
From$109*
Seen: 10 hrs ago
One Way/Basic
Oct 2026
From$109*
Seen: 8 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $109
cmp-daily-histogram-bars-legend-max-price-aria-label $189
Displaying fares for August-2026
  • MDW–BOS, 08/24/2026: From $169
    24

    Mon

    AUG

  • MDW–BOS, 08/25/2026: From $169
    25

    Tue

  • MDW–BOS, 08/26/2026: From $169
    26

    Wed

  • MDW–BOS, 08/27/2026: From $169
    27

    Thu

  • MDW–BOS, 08/28/2026: From $169
    28

    Fri

  • MDW–BOS, 08/29/2026: From $169
    29

    Sat

  • MDW–BOS, 08/30/2026: From $169
    30

    Sun

  • MDW–BOS, 08/31/2026: From $169
    31

    Mon

  • MDW–BOS, 09/01/2026: From $169
    01

    Tue

    SEP

  • MDW–BOS, 09/02/2026: From $169
    02

    Wed

  • MDW–BOS, 09/03/2026: From $169
    03

    Thu

  • MDW–BOS, 09/04/2026: From $189
    04

    Fri

  • MDW–BOS, 09/05/2026: From $148
    05

    Sat

  • MDW–BOS, 09/06/2026: From $148
    06

    Sun

  • MDW–BOS, 09/07/2026: From $138
    07

    Mon

  • MDW–BOS, 09/08/2026: From $128
    08

    Tue

  • MDW–BOS, 09/09/2026: From $128
    09

    Wed

  • MDW–BOS, 09/10/2026: From $128
    10

    Thu

  • MDW–BOS, 09/11/2026: From $128
    11

    Fri

  • MDW–BOS, 09/12/2026: From $128
    12

    Sat

  • MDW–BOS, 09/13/2026: From $128
    13

    Sun

  • MDW–BOS, 09/14/2026: From $109
    14

    Mon

  • MDW–BOS, 09/15/2026: From $109
    15

    Tue

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

    Wed

  • MDW–BOS, 09/17/2026: From $109
    17

    Thu

  • MDW–BOS, 09/18/2026: From $158
    18

    Fri

  • MDW–BOS, 09/19/2026: From $128
    19

    Sat

  • MDW–BOS, 09/20/2026: From $128
    20

    Sun

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

    Mon

  • MDW–BOS, 09/22/2026: From $109
    22

    Tue

  • MDW–BOS, 09/23/2026: From $128
    23

    Wed

    • Range$109-$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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