Southwest® flights from Orlando to Boston from $100

Promo Code

Low fares from Orlando to Boston

$

Orlando (MCO)to

Boston (BOS)
Depart: 10/20/2026

One-way

Basic

From
$100
Seen: 3 hrs ago

Orlando (MCO)to

Boston (BOS)
Depart: 10/07/2026

One-way

Basic

From
$100
Seen: 5 hrs ago

Orlando (MCO)to

Boston (BOS)
Depart: 11/03/2026

One-way

Basic

From
$100
Seen: 13 hrs ago

Orlando (MCO)to

Boston (BOS)
Depart: 11/14/2026

One-way

Basic

From
$105
Seen: 20 hrs ago

Orlando (MCO)to

Boston (BOS)
Depart: 10/20/2026

One-way

Choice

From
$145
Seen: 3 hrs ago

Orlando (MCO)to

Boston (BOS)
Depart: 11/03/2026

One-way

Choice

From
$145
Seen: 13 hrs ago

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Explore flights from Orlando to Boston

Sep 2026
From$210*
Seen: 10 hrs ago
One Way/Basic
Oct 2026
From$100*
Seen: 5 hrs ago
One Way/Basic
Nov 2026
From$100*
Seen: 13 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $100
cmp-daily-histogram-bars-legend-max-price-aria-label $362
Displaying fares for September-2026
  • MCO–BOS, 09/12/2026: From $210
    12

    Sat

    SEP

  • MCO–BOS, 09/13/2026: From $246
    13

    Sun

  • MCO–BOS, 09/14/2026: From $256
    14

    Mon

  • MCO–BOS, 09/15/2026: From $215
    15

    Tue

  • MCO–BOS, 09/16/2026: From $215
    16

    Wed

  • MCO–BOS, 09/17/2026: From $256
    17

    Thu

  • MCO–BOS, 09/18/2026: From $256
    18

    Fri

  • MCO–BOS: cmp-view-offers-disclaimer. Find Offers
    19

    Sat

  • MCO–BOS, 09/20/2026: From $256
    20

    Sun

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

    Mon

  • MCO–BOS, 09/22/2026: From $215
    22

    Tue

  • MCO–BOS, 09/23/2026: From $215
    23

    Wed

  • MCO–BOS, 09/24/2026: From $362
    24

    Thu

  • MCO–BOS, 09/25/2026: From $259
    25

    Fri

  • MCO–BOS, 09/26/2026: From $220
    26

    Sat

  • MCO–BOS, 09/27/2026: From $289
    27

    Sun

  • MCO–BOS, 09/28/2026: From $254
    28

    Mon

  • MCO–BOS, 09/29/2026: From $215
    29

    Tue

  • MCO–BOS, 09/30/2026: From $215
    30

    Wed

  • MCO–BOS, 10/01/2026: From $254
    01

    Thu

    OCT

  • MCO–BOS, 10/02/2026: From $229
    02

    Fri

  • MCO–BOS, 10/03/2026: From $186
    03

    Sat

  • MCO–BOS, 10/04/2026: From $276
    04

    Sun

  • MCO–BOS, 10/05/2026: From $218
    05

    Mon

  • MCO–BOS: cmp-view-offers-disclaimer. Find Offers
    06

    Tue

  • MCO–BOS, 10/07/2026: From $100
    07

    Wed

  • MCO–BOS, 10/08/2026: From $257
    08

    Thu

  • MCO–BOS, 10/09/2026: From $276
    09

    Fri

  • MCO–BOS, 10/10/2026: From $215
    10

    Sat

  • MCO–BOS, 10/11/2026: From $234
    11

    Sun

    • Range$100-$362

    *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:
    Orlando International Airport
    Arriving at:
    Logan International Airport
    Distance:
    1121 miles

    Route Information

    154† 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 154 weekly flights from Orlando to Boston on Southwest Airlines.
    To find the lowest fares by day and time to fly Orlando 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 Orlando 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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