Southwest® flights from Fort Myers/Naples to Boston from $95

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Low fares from Fort Myers/Naples to Boston

$

Fort Myers/Naples (RSW)to

Boston (BOS)
Depart: 10/31/2026

One-way

Basic

From
$95
Seen: 10 hrs ago

Fort Myers/Naples (RSW)to

Boston (BOS)
Depart: 10/07/2026

One-way

Basic

From
$100
Seen: 7 hrs ago

Fort Myers/Naples (RSW)to

Boston (BOS)
Depart: 10/21/2026

One-way

Basic

From
$100
Seen: 3 hrs ago

Fort Myers/Naples (RSW)to

Boston (BOS)
Depart: 11/11/2026

One-way

Basic

From
$100
Seen: 2 hrs ago

Fort Myers/Naples (RSW)to

Boston (BOS)
Depart: 10/06/2026

One-way

Basic

From
$100
Seen: 8 hrs ago

Fort Myers/Naples (RSW)to

Boston (BOS)
Depart: 11/10/2026

One-way

Basic

From
$100
Seen: 12 hrs ago

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Explore flights from Fort Myers/Naples to Boston

Sep 2026
From$234*
Seen: 17 hrs ago
One Way/Basic
Oct 2026
From$95*
Seen: 10 hrs ago
One Way/Basic
Nov 2026
From$100*
Seen: 12 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $100
cmp-daily-histogram-bars-legend-max-price-aria-label $414
Displaying fares for September-2026
  • RSW–BOS, 09/11/2026: From $414
    11

    Fri

    SEP

  • RSW–BOS, 09/12/2026: From $364
    12

    Sat

  • RSW–BOS, 09/13/2026: From $364
    13

    Sun

  • RSW–BOS, 09/14/2026: From $364
    14

    Mon

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

    Tue

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

    Wed

  • RSW–BOS, 09/17/2026: From $314
    17

    Thu

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

    Fri

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

    Sat

  • RSW–BOS, 09/20/2026: From $314
    20

    Sun

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

    Mon

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

    Tue

  • RSW–BOS, 09/23/2026: From $314
    23

    Wed

  • RSW–BOS, 09/24/2026: From $289
    24

    Thu

  • RSW–BOS, 09/25/2026: From $245
    25

    Fri

  • RSW–BOS, 09/26/2026: From $239
    26

    Sat

  • RSW–BOS, 09/27/2026: From $234
    27

    Sun

  • RSW–BOS, 09/28/2026: From $234
    28

    Mon

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

    Tue

  • RSW–BOS, 09/30/2026: From $234
    30

    Wed

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

    Thu

    OCT

  • RSW–BOS, 10/02/2026: From $234
    02

    Fri

  • RSW–BOS, 10/03/2026: From $100
    03

    Sat

  • RSW–BOS: cmp-view-offers-disclaimer. Find Offers
    04

    Sun

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

    Mon

  • RSW–BOS, 10/06/2026: From $100
    06

    Tue

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

    Wed

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

    Thu

  • RSW–BOS, 10/09/2026: From $234
    09

    Fri

  • RSW–BOS, 10/10/2026: From $194
    10

    Sat

    • Range$100-$414

    *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

    Route Information

    134† 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 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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