Southwest® flights from Boston to Fort Myers/Naples from $100

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Low fares from Boston to Fort Myers/Naples

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Boston (BOS)to

Fort Myers/Naples (RSW)
Depart: 11/11/2026

One-way

Basic

From
$100
Seen: 5 hrs ago

Boston (BOS)to

Fort Myers/Naples (RSW)
Depart: 11/03/2026

One-way

Basic

From
$100
Seen: 9 hrs ago

Boston (BOS)to

Fort Myers/Naples (RSW)
Depart: 11/04/2026

One-way

Basic

From
$105
Seen: 18 hrs ago

Boston (BOS)to

Fort Myers/Naples (RSW)
Depart: 01/06/2027

One-way

Basic

From
$125
Seen: 2 hrs ago

Boston (BOS)to

Fort Myers/Naples (RSW)
Depart: 12/04/2026

One-way

Basic

From
$140
Seen: 21 hrs ago

Boston (BOS)to

Fort Myers/Naples (RSW)
Depart: 12/10/2026

One-way

Basic

From
$140
Seen: 12 hrs ago

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Explore flights from Boston to Fort Myers/Naples

Oct 2026
From$209*
Seen: 17 hrs ago
One Way/Basic
Nov 2026
From$100*
Seen: 9 hrs ago
One Way/Basic
Dec 2026
From$140*
Seen: 12 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $209
cmp-daily-histogram-bars-legend-max-price-aria-label $374
Displaying fares for October-2026
  • BOS–RSW: cmp-view-offers-disclaimer. Find Offers
    01

    Thu

    OCT

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

    Fri

  • BOS–RSW, 10/03/2026: From $374
    03

    Sat

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    04

    Sun

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    05

    Mon

  • BOS–RSW, 10/06/2026: From $374
    06

    Tue

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    07

    Wed

  • BOS–RSW, 10/08/2026: From $324
    08

    Thu

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    09

    Fri

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

    Sat

  • BOS–RSW: cmp-view-offers-disclaimer. Find Offers
    11

    Sun

  • BOS–RSW, 10/12/2026: From $324
    12

    Mon

  • BOS–RSW, 10/13/2026: From $324
    13

    Tue

  • BOS–RSW: cmp-view-offers-disclaimer. Find Offers
    14

    Wed

  • BOS–RSW, 10/15/2026: From $244
    15

    Thu

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

    Fri

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

    Sat

  • BOS–RSW, 10/18/2026: From $324
    18

    Sun

  • BOS–RSW, 10/19/2026: From $309
    19

    Mon

  • BOS–RSW, 10/20/2026: From $244
    20

    Tue

  • BOS–RSW, 10/21/2026: From $209
    21

    Wed

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

    Thu

  • BOS–RSW: cmp-view-offers-disclaimer. Find Offers
    23

    Fri

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    24

    Sat

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

    Sun

  • BOS–RSW, 10/26/2026: From $209
    26

    Mon

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    27

    Tue

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    28

    Wed

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    29

    Thu

  • BOS–RSW, 10/30/2026: From $214
    30

    Fri

  • BOS–RSW: cmp-view-offers-disclaimer. Find Offers
    31

    Sat

    • Range$209-$374

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

    Route Information

    124† 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 124 weekly flights from Boston to Fort Myers/Naples on Southwest Airlines.
    To find the lowest fares by day and time to fly Boston to Fort Myers/Naples with Southwest, check out our Low Fare Calendar.
    You can rent a car at Southwest Florida Regional Airport book yours with your flight.
    Yes! Flights from Boston to Fort Myers/Naples—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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