Southwest® flights from Orlando to Boston from $100

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Low fares from Orlando to Boston

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Orlando (MCO)to

Boston (BOS)
Depart: 01/29/2027

One-way

Basic

From
$100
Seen: 8 hrs ago

Orlando (MCO)to

Boston (BOS)
Depart: 01/06/2027

One-way

Basic

From
$100
Seen: 22 hrs ago

Orlando (MCO)to

Boston (BOS)
Depart: 01/07/2027

One-way

Basic

From
$100
Seen: 6 hrs ago

Orlando (MCO)to

Boston (BOS)
Depart: 01/15/2027

One-way

Basic

From
$105
Seen: 17 hrs ago

Orlando (MCO)to

Boston (BOS)
Depart: 01/20/2027

One-way

Basic

From
$105
Seen: 2 hrs ago

Orlando (MCO)to

Boston (BOS)
Depart: 01/05/2027

One-way

Basic

From
$105
Seen: 1 hour ago

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Explore flights from Orlando to Boston

Nov 2026
From$182*
Seen: 10 hrs ago
One Way/Basic
Dec 2026
From$105*
Seen: 12 hrs ago
One Way/Basic
Jan 2027
From$100*
Seen: 22 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $105
cmp-daily-histogram-bars-legend-max-price-aria-label $518
Displaying fares for November-2026
  • MCO–BOS, 11/13/2026: From $291
    13

    Fri

    NOV

  • MCO–BOS, 11/14/2026: From $250
    14

    Sat

  • MCO–BOS: cmp-view-offers-disclaimer. Find Offers
    15

    Sun

  • MCO–BOS, 11/16/2026: From $291
    16

    Mon

  • MCO–BOS, 11/17/2026: From $250
    17

    Tue

  • MCO–BOS, 11/18/2026: From $245
    18

    Wed

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

    Thu

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

    Fri

  • MCO–BOS, 11/21/2026: From $221
    21

    Sat

  • MCO–BOS: cmp-view-offers-disclaimer. Find Offers
    22

    Sun

  • MCO–BOS, 11/23/2026: From $221
    23

    Mon

  • MCO–BOS: cmp-view-offers-disclaimer. Find Offers
    24

    Tue

  • MCO–BOS, 11/25/2026: From $182
    25

    Wed

  • MCO–BOS, 11/26/2026: From $182
    26

    Thu

  • MCO–BOS, 11/27/2026: From $209
    27

    Fri

  • MCO–BOS, 11/28/2026: From $319
    28

    Sat

  • MCO–BOS, 11/29/2026: From $518
    29

    Sun

  • MCO–BOS, 11/30/2026: From $319
    30

    Mon

  • MCO–BOS, 12/01/2026: From $174
    01

    Tue

    DEC

  • MCO–BOS: cmp-view-offers-disclaimer. Find Offers
    02

    Wed

  • MCO–BOS: cmp-view-offers-disclaimer. Find Offers
    03

    Thu

  • MCO–BOS, 12/04/2026: From $174
    04

    Fri

  • MCO–BOS, 12/05/2026: From $145
    05

    Sat

  • MCO–BOS, 12/06/2026: From $229
    06

    Sun

  • MCO–BOS, 12/07/2026: From $199
    07

    Mon

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

    Tue

  • MCO–BOS, 12/09/2026: From $145
    09

    Wed

  • MCO–BOS: cmp-view-offers-disclaimer. Find Offers
    10

    Thu

  • MCO–BOS, 12/11/2026: From $105
    11

    Fri

  • MCO–BOS, 12/12/2026: From $105
    12

    Sat

    • Range$105-$518

    *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

    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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