Southwest® flights from Fort Myers/Naples to Boston from $214

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Low fares from Fort Myers/Naples to Boston

$

Fort Myers/Naples (RSW)to

Boston (BOS)
Depart: 02/03/2027

One-way

Basic

From
$214
Seen: 19 hrs ago

Fort Myers/Naples (RSW)to

Boston (BOS)
Depart: 12/23/2026

One-way

Basic

From
$217
Seen: 17 hrs ago

Fort Myers/Naples (RSW)to

Boston (BOS)
Depart: 12/18/2026

One-way

Basic

From
$217
Seen: 14 hrs ago

Fort Myers/Naples (RSW)to

Boston (BOS)
Depart: 12/19/2026

One-way

Basic

From
$217
Seen: 9 hrs ago

Fort Myers/Naples (RSW)to

Boston (BOS)
Depart: 12/25/2026

One-way

Basic

From
$217
Seen: 17 hrs ago

Fort Myers/Naples (RSW)to

Boston (BOS)
Depart: 12/09/2026

One-way

Basic

From
$219
Seen: 6 hrs ago

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Explore flights from Fort Myers/Naples to Boston

Nov 2026
From$220*
Seen: 20 hrs ago
One Way/Basic
Dec 2026
From$217*
Seen: 17 hrs ago
One Way/Basic
Jan 2027
From$239*
Seen: 6 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $219
cmp-daily-histogram-bars-legend-max-price-aria-label $449
Displaying fares for November-2026
  • RSW–BOS, 11/11/2026: From $449
    11

    Wed

    NOV

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

    Thu

  • RSW–BOS, 11/13/2026: From $394
    13

    Fri

  • RSW–BOS, 11/14/2026: From $399
    14

    Sat

  • RSW–BOS, 11/15/2026: From $404
    15

    Sun

  • RSW–BOS, 11/16/2026: From $349
    16

    Mon

  • RSW–BOS, 11/17/2026: From $404
    17

    Tue

  • RSW–BOS: cmp-view-offers-disclaimer. Find Offers
    18

    Wed

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

    Thu

  • RSW–BOS, 11/20/2026: From $344
    20

    Fri

  • RSW–BOS, 11/21/2026: From $354
    21

    Sat

  • RSW–BOS, 11/22/2026: From $344
    22

    Sun

  • RSW–BOS, 11/23/2026: From $230
    23

    Mon

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

    Tue

  • RSW–BOS, 11/25/2026: From $220
    25

    Wed

  • RSW–BOS: cmp-view-offers-disclaimer. Find Offers
    26

    Thu

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

    Fri

  • RSW–BOS: cmp-view-offers-disclaimer. Find Offers
    28

    Sat

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

    Sun

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

    Mon

  • RSW–BOS: cmp-view-offers-disclaimer. Find Offers
    01

    Tue

    DEC

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

    Wed

  • RSW–BOS, 12/03/2026: From $239
    03

    Thu

  • RSW–BOS, 12/04/2026: From $239
    04

    Fri

  • RSW–BOS: cmp-view-offers-disclaimer. Find Offers
    05

    Sat

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

    Sun

  • RSW–BOS: cmp-view-offers-disclaimer. Find Offers
    07

    Mon

  • RSW–BOS, 12/08/2026: From $219
    08

    Tue

  • RSW–BOS, 12/09/2026: From $219
    09

    Wed

  • RSW–BOS, 12/10/2026: From $239
    10

    Thu

    • Range$219-$449

    *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:
    Southwest Florida Regional Airport
    Arriving at:
    Logan International Airport
    Distance:
    1249 miles

    Questions we hear the most

    There are 134 weekly flights from Fort Myers/Naples to Boston on Southwest Airlines.
    To find the lowest fares by day and time to fly Fort Myers/Naples 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 Fort Myers/Naples 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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