Southwest® flights from Chicago-Midway to Boston from $101

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Low fares from Chicago-Midway to Boston

$

Chicago-Midway (MDW)to

Boston (BOS)
Depart: 12/09/2026

One-way

Basic

From
$101
Seen: 1 hour ago

Chicago-Midway (MDW)to

Boston (BOS)
Depart: 12/23/2026

One-way

Basic

From
$101
Seen: 9 hrs ago

Chicago-Midway (MDW)to

Boston (BOS)
Depart: 11/02/2026

One-way

Basic

From
$101
Seen: 8 hrs ago

Chicago-Midway (MDW)to

Boston (BOS)
Depart: 01/07/2027

One-way

Basic

From
$101
Seen: 8 hrs ago

Chicago-Midway (MDW)to

Boston (BOS)
Depart: 11/18/2026

One-way

Basic

From
$101
Seen: 10 hrs ago

Chicago-Midway (MDW)to

Boston (BOS)
Depart: 11/17/2026

One-way

Basic

From
$101
Seen: 10 hrs ago

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Explore flights from Chicago-Midway to Boston

Oct 2026
From$101*
Seen: 3 hrs ago
One Way/Basic
Nov 2026
From$101*
Seen: 19 hrs ago
One Way/Basic
Dec 2026
From$101*
Seen: 1 hour ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $101
cmp-daily-histogram-bars-legend-max-price-aria-label $296
Displaying fares for October-2026
  • MDW–BOS, 10/05/2026: From $296
    05

    Mon

    OCT

  • MDW–BOS, 10/06/2026: From $284
    06

    Tue

  • MDW–BOS, 10/07/2026: From $284
    07

    Wed

  • MDW–BOS, 10/08/2026: From $296
    08

    Thu

  • MDW–BOS, 10/09/2026: From $296
    09

    Fri

  • MDW–BOS, 10/10/2026: From $284
    10

    Sat

  • MDW–BOS, 10/11/2026: From $296
    11

    Sun

  • MDW–BOS: cmp-view-offers-disclaimer. Find Offers
    12

    Mon

  • MDW–BOS, 10/13/2026: From $284
    13

    Tue

  • MDW–BOS, 10/14/2026: From $284
    14

    Wed

  • MDW–BOS, 10/15/2026: From $295
    15

    Thu

  • MDW–BOS, 10/16/2026: From $296
    16

    Fri

  • MDW–BOS: cmp-view-offers-disclaimer. Find Offers
    17

    Sat

  • MDW–BOS, 10/18/2026: From $198
    18

    Sun

  • MDW–BOS, 10/19/2026: From $158
    19

    Mon

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

    Tue

  • MDW–BOS, 10/21/2026: From $158
    21

    Wed

  • MDW–BOS, 10/22/2026: From $158
    22

    Thu

  • MDW–BOS, 10/23/2026: From $189
    23

    Fri

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

    Sat

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

    Sun

  • MDW–BOS, 10/26/2026: From $101
    26

    Mon

  • MDW–BOS, 10/27/2026: From $158
    27

    Tue

  • MDW–BOS, 10/28/2026: From $101
    28

    Wed

  • MDW–BOS, 10/29/2026: From $101
    29

    Thu

  • MDW–BOS, 10/30/2026: From $168
    30

    Fri

  • MDW–BOS, 10/31/2026: From $158
    31

    Sat

  • MDW–BOS, 11/01/2026: From $158
    01

    Sun

    NOV

  • MDW–BOS, 11/02/2026: From $101
    02

    Mon

  • MDW–BOS, 11/03/2026: From $101
    03

    Tue

  • MDW–BOS, 11/04/2026: From $101
    04

    Wed

    • Range$101-$296

    *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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