Other Destinations
Fort Myers (RSW) to Nashville (BNA) in October from $216
From $216
Fort Myers (RSW) to State College (SCE) in October from $339
From $339
Fort Myers (RSW) to Nashville (BNA) in November from $216
From $216
Fort Myers (RSW) to Grand Junction (GJT) in November from $249
From $249
Fort Myers (RSW) to Burbank (BUR) in November from $278
From $278
Fort Myers (RSW) to Dallas (DFW) in November from $327
From $327
Flights from Other Cities
Miami (MIA) to Boston (BOS) in October from $44
From $44
Cleveland (CLE) to Boston (BOS) in October from $114
From $114
Dallas (DFW) to Boston (BOS) in October from $134
From $134
Atlanta (ATL) to Boston (BOS) in October from $137
From $137
San Francisco (SFO) to Boston (BOS) in October from $149
From $149
Cleveland (CLE) to Boston (BOS) in October from $154
From $154
✈️ Flight Guide: Fort Myers (RSW) → Boston (BOS)
Complete travel information for your October journey
October departures from Southwest Florida International Airport (RSW) to Boston Logan International Airport (BOS) offer a balance of lower shoulder-season fares and comfortable travel weather. Fort Myers area travelers (including those from Naples and Cape Coral) should watch for Columbus Day weekend demand and consider midweek flights to save. Book 2–6 weeks ahead for the best combination of price and schedule flexibility, enable fare alerts for RSW to BOS, and pack layers for Boston’s cooler mornings. Check RSW terminal maps, TSA wait times, and arrive 90–120 minutes early. If flights sell out, nearby airports like Sarasota-Bradenton and Punta Gorda can be alternatives. CTA: Search and book RSW to BOS flights now to lock in October savings.
Departing from Fort Myers (RSW) FAQs
Direct flights from Southwest Florida International Airport (RSW) to Boston Logan International Airport (BOS) operate seasonally and year-round depending on the carrier, with typical nonstop flight time around 3 hours 15 minutes. In October you can find both nonstop and one-stop options — search evening midweek nonstops for the best fares. Book early for holiday weekends and consider nearby airports (Naples, Cape Coral, Sarasota) if RSW schedules are limited.
A nonstop flight from Southwest Florida International Airport (RSW) to Boston Logan International Airport (BOS) typically takes about 3 hours 10–3 hours 30 minutes depending on winds and routing. Allow extra time for boarding, taxiing, and potential seasonal delays in October due to regional weather changes, and always check real-time status before leaving for the airport.
October is a shoulder-season month: demand can be lower than summer but higher around Columbus Day and the Head of the Charles Regatta in Boston. You can often find lower midweek fares if you book 2–6 weeks in advance and use fare alerts, flexible dates, or compare airlines like JetBlue and Delta for promotional pricing.
October trips require layered clothing — light shirts for Fort Myers warmth and a medium-weight jacket for Boston's cool mornings and evenings. Include an umbrella for occasional New England rain, comfortable walking shoes for city sightseeing in Boston and Cambridge, and a travel adapter or portable charger for long travel days.
For domestic flights from Southwest Florida International Airport (RSW) to Boston Logan International Airport (BOS), arrive at least 90 minutes before departure. During October weekends, holidays, and peak morning or evening waves, allow 2 hours for check-in and TSA security lines. Use online check-in and mobile boarding passes to speed your airport experience.
October is toward the end of Atlantic hurricane season but storms can still occur. Monitor NOAA and airline advisories before traveling, purchase flexible fares or travel insurance, and check the Southwest Florida International Airport (RSW) website for operational updates. Many carriers offer waivers or rebooking during severe weather events.
October arrivals at Boston Logan International Airport (BOS) signal fall foliage, cooler temps, and special events such as the Head of the Charles Regatta and Salem Halloween festivities. After landing from Southwest Florida International Airport (RSW), choose MBTA Silver Line or ride-share to reach downtown Boston efficiently. Expect crisp mornings—pack layers and an umbrella—and book ground transport and parking early around event weekends. For additional explorations, combine city stays with day trips to Cambridge, Salem, Providence, or scenic routes to Cape Cod. CTA: Book your RSW to BOS flights now and reserve Logan Airport parking and ground transport for October travel.
Arriving at Boston (BOS) FAQs
From Boston Logan International Airport (BOS), the fastest public option is the MBTA Silver Line bus (SL1) to South Station; taxis and ride-shares provide door-to-door service with typical travel times of 15–30 minutes to downtown depending on traffic. In October, expect slightly heavier traffic during event weekends like the Head of the Charles Regatta, so plan extra time and consider taking public transit for scheduled arrivals.
October in Boston is crisp and cool, with average daytime highs of 55–65°F (13–18°C) and chilly evenings. Pack layers and a light jacket for arrival; fall foliage usually peaks later in October depending on the year, offering scenic drives to Cambridge, Salem, and Cape Cod.
Boston Logan International Airport (BOS) has multiple lounges (Airline-branded and pay-per-use) across terminals, baggage storage services, and car rental desks. In October, many services operate normally but may adjust hours for special events; check BOS terminal maps and airline apps for current lounge access rules and locations.
From Boston Logan International Airport (BOS) you can access Cambridge, Quincy, Salem, Providence, Worcester, and scenic Cape Cod. October is ideal for day trips to Salem for Halloween events, the Head of the Charles in Cambridge, or foliage drives to the Berkshires and northern New England.
As of October travel guidance, most U.S. domestic airports including Boston Logan International Airport (BOS) follow CDC and TSA guidance; mask mandates are generally lifted but airlines or local jurisdictions may have specific recommendations. Check airline and airport health advisories before travel and consider travel insurance for flexibility during changing conditions.
Boston Logan International Airport (BOS) offers on-site parking (central and economy lots) and off-site shuttle lots; availability can be limited during October events, so reserve a spot in advance for weekend travel. Consider off-site lots or taking a taxi/ride-share for shorter trips to downtown Boston or Cambridge.
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October Events & Festivals Near RSW and BOS — Plan Around Headliners
Boston area highlights in October: Head of the Charles Regatta (late October) draws large crowds and higher flight/hotel demand; Salem Halloween attractions and Haunted Happenings make October popular for New England visitors; local college events in Cambridge (Harvard/Yale sporting weekends) can also influence travel. Southwest Florida (Fort Myers area) in October offers quieter beaches, seafood festivals, and golf tournaments with milder temperatures after summer. Plan travel around peak event dates—book RSW to BOS flights and Boston hotels early if your trip coincides with regattas or Halloween events. CTA: Check event dates and reserve flights and lodging for October as soon as possible.
Best Time to Fly RSW to BOS in October — Save Money & Avoid Crowds
For October travel from Southwest Florida International Airport (RSW) to Boston Logan International Airport (BOS), fly midweek (Tuesday–Thursday) and outside Columbus Day weekend to secure lower fares and shorter lines. Early morning or late evening flights often mean fewer delays and better seat availability. If you want peak foliage, aim for late October but book early as demand rises for weekends; if you prefer cheaper fares and quieter streets, choose early to mid-October midweek departures. CTA: Compare midweek RSW to BOS flights now and lock in the best schedule for October.
Direct vs Connecting Flights: RSW to BOS — Pros, Cons & October Considerations
Nonstop flights from Southwest Florida International Airport (RSW) to Boston Logan International Airport (BOS) are fastest (about 3h15) and reduce risk of missed connections, making them ideal for short October trips or tight itineraries. Connecting flights via hubs like Atlanta (ATL) or Charlotte (CLT) can be cheaper and offer more schedule options, but add potential delay risk and longer total travel time. If you’re traveling with checked bags or during busy fall event weekends, prefer nonstop for reliability; if you need the lowest fare or more departure times, a one-stop itinerary may be better. CTA: Compare nonstop and connecting RSW to BOS flights for your October dates and choose based on convenience or savings.
Airline Comparison for RSW to BOS Flights in October — JetBlue, Delta, American & More
JetBlue: Known for competitive nonstop schedules between Southwest Florida International Airport (RSW) and Boston Logan International Airport (BOS), more legroom options, and free Wi-Fi; good for comfort on October flights. Delta: Offers reliable service with hub connections (ATL) and strong on-time performance; consider SkyMiles perks. American: May offer one-stop options through Charlotte (CLT) or Philadelphia (PHL) with AAdvantage benefits. Spirit/Frontier: Often provide the lowest base fares but add fees for carry-ons and seat assignments—best if you travel light. For October travel, compare total trip cost (including baggage and seat fees) and loyalty benefits. CTA: Run a side-by-side airline comparison for your October RSW to BOS travel dates before booking.
Seasonal Travel Tips for RSW to BOS in October — Packing, Weather & Flexibility
Pack layers when flying from Southwest Florida International Airport (RSW) to Boston Logan International Airport (BOS) in October — light clothing for Fort Myers and a warm jacket for Boston evenings. Monitor weather forecasts for late-season tropical activity and buy flexible tickets or travel insurance if you’re concerned about disruptions. Arrive at RSW 90–120 minutes before departure, use mobile boarding to speed check-in, and reserve Logan Airport ground transport in advance for event weekends. Consider midweek travel to save on fares and avoid heavy weekend crowds tied to holidays and festivals. CTA: Prepare your October RSW to BOS trip now — pack smart, secure flexible fares, and sign up for flight alerts.
Flight Time & Schedules: Southwest Florida International Airport (RSW) to Boston Logan International Airport (BOS)
Typical nonstop flights from Southwest Florida International Airport (RSW) to Boston Logan International Airport (BOS) take approximately 3 hours 10 minutes to 3 hours 30 minutes, with both airports operating in Eastern Time (no timezone change needed). In October, expect multiple weekly nonstops on larger carriers and additional one-stop options through hubs like Atlanta (ATL) or Charlotte (CLT). Sample weekday schedule windows: morning departures (6:00–9:00), midday (11:00–14:00), and evening (17:00–21:00). Always verify current schedules as airlines adjust frequencies for shoulder season demand. CTA: Check real-time flight schedules and pick the nonstop that fits your October itinerary.
Find Cheap RSW to BOS Flights in October — Tips & Strategies
Primary strategies to find cheap RSW to BOS flights in October include booking 2–6 weeks in advance, flying midweek (Tuesdays and Wednesdays are often cheapest), and being flexible with departure/return dates. Set fare alerts for Southwest Florida International Airport (RSW) to Boston Logan International Airport (BOS), and compare nonstop versus one-stop itineraries via Atlanta (ATL) or Charlotte (CLT) for deeper discounts. Use nearby airports like Sarasota-Bradenton (SRQ) or Punta Gorda (PGD) as backup options for better rates. Consider basic economy fares for steep discounts but check baggage and seat assignment fees. CTA: Set a fare alert now to track RSW to BOS October price drops.