Best Flights starting from $322
from$322economy
Fort Myers (RSW)
Tue, Oct 20
Roundtrip
Westchester County (HPN)
Thu, Oct 22
from$322economy
Fort Myers (RSW)
Mon, Oct 26
Roundtrip
Westchester County (HPN)
Wed, Oct 28
from$323economy
Fort Myers (RSW)
Wed, Oct 21
Roundtrip
Westchester County (HPN)
Fri, Oct 23
from$323economy
Fort Myers (RSW)
Sun, Oct 25
Roundtrip
Westchester County (HPN)
Tue, Oct 27
from$329economy
Fort Myers (RSW)
Sat, Oct 24
Roundtrip
Westchester County (HPN)
Mon, Oct 26
from$337economy
Fort Myers (RSW)
Thu, Oct 22
Roundtrip
Westchester County (HPN)
Sat, Oct 24
from$337economy
Fort Myers (RSW)
Fri, Oct 23
Roundtrip
Westchester County (HPN)
Sun, Oct 25
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Other Options for This Route
Other Destinations
Fort Myers (RSW) to Philadelphia (Any) in October from $90
From $90
Fort Myers (RSW) to Providence (PVD) in October from $94
From $94
Fort Myers (RSW) to Boston (BOS) in October from $99
From $99
Fort Myers (RSW) to Chicago (ORD) in October from $138
From $138
Fort Myers (RSW) to Newark (EWR) in October from $202
From $202
Fort Myers (RSW) to Seattle (SEA) in October from $213
From $213
Flights from Other Cities
Atlanta (ATL) to Westchester County (HPN) in October from $227
From $227
Asheville (AVL) to Westchester County (HPN) in October from $311
From $311
Louisville (SDF) to Westchester County (HPN) in October from $402
From $402
Savannah (SAV) to Westchester County (HPN) in November from $387
From $387
Birmingham (BHM) to Westchester County (HPN) in November from $539
From $539
West Palm Beach (PBI) to Westchester County (HPN) in December from $174
From $174
✈️ Flight Guide: Fort Myers (RSW) → Westchester County (HPN)
Complete travel information for your October journey
October is a favorable month to fly from Southwest Florida International Airport (RSW) to Westchester County Airport (HPN). Cooler temperatures in the Northeast and lower shoulder-season fares make it attractive for both leisure and business travelers. Expect one-stop itineraries via major hubs; book midweek flights to capture lower October fares.
Departing from Fort Myers (RSW) FAQs
Routes from Southwest Florida International Airport (RSW) to Westchester County Airport (HPN) are typically served by major carriers like American Airlines and Delta with one-stop connections via their hubs; seasonal and multi-carrier itineraries may include JetBlue or Southwest connecting through other airports. Check carrier schedules and book early for October travel to secure the best RSW to HPN flights and preferred connection times.
Typical total travel time from Southwest Florida International Airport (RSW) to Westchester County Airport (HPN) ranges from about 4.5 to 7 hours including one connection, depending on layover length and routing; there are no regular nonstop flights as of October. For the fastest itinerary, search for one-stop options with short connections in hubs like Charlotte or Philadelphia for quicker RSW to HPN travel.
October can offer lower fares on Southwest Florida International Airport (RSW) to Westchester County Airport (HPN) routes compared with peak summer months, especially midweek and outside of Columbus Day weekend. To find cheap flights RSW to HPN in October, compare flexible dates, sign up for fare alerts, and book 3–8 weeks in advance for the best airfare deals.
Southwest Florida International Airport (RSW) offers car rental centers, ride-share pickup zones, and shuttle services to Fort Myers, Naples, and Cape Coral; allow extra time for traffic and security if transferring to a connection for Westchester County Airport (HPN). For October departures, check local traffic for seasonal events and arrive at least 2 hours before domestic flights to ensure smooth RSW to HPN connections.
October in Southwest Florida typically has lower hurricane risk than earlier fall months, but afternoon thunderstorms or residual tropical activity can still cause delays at Southwest Florida International Airport (RSW). When booking RSW to HPN flights in October, monitor weather forecasts and choose itineraries with manageable connection buffers to reduce the chance of missed flights.
Southwest Florida International Airport (RSW) offers a limited selection of lounges, priority security lanes with certain airlines, and pay-per-use amenities; executive and premium cabin travelers should verify lounge access with their carrier. For travelers seeking a comfortable start to an RSW to HPN trip in October, consider booking airlines that offer priority boarding or credit card lounge benefits.
Arriving at Westchester County Airport (HPN) in October from Southwest Florida International Airport (RSW) offers quick access to White Plains, Manhattan, the Hudson Valley, and southwestern Connecticut. October sees pleasant fall foliage and many cultural events, so plan for busier weekends and book ground transportation early.
Arriving at Westchester County (HPN) FAQs
Westchester County Airport (HPN) offers ride-shares, taxis, shuttle services, and regional car rentals that connect travelers to White Plains, Yonkers, and New York City; peak October weekends may see higher demand so pre-book transfers if needed. For cost-effective travel into Manhattan, consider shuttle services or commuter rail connections from nearby White Plains with a short taxi from the airport.
October brings higher travel to Westchester County Airport (HPN) due to fall festivals, college football weekends, and proximity to New York City events such as New York Comic Con and Halloween activities. Expect moderate increases in demand on weekends; book RSW to HPN flights early and allow extra time for ground transfers during October events.
Westchester County Airport (HPN) has streamlined baggage claim and short walking distances to ground transport; check your connecting airline's baggage policy when booking RSW to HPN itineraries. For October trips, label bags clearly, check arrival terminal procedures, and confirm ground transport options ahead of arrival to White Plains or nearby destinations.
Yes, there are several hotels within a short drive of Westchester County Airport (HPN), ranging from economy to business-class properties near White Plains and downtown Yonkers; booking in October is recommended for weekends and event dates. Use location-based searches for hotels with shuttle service to HPN to simplify arrival logistics from RSW.
After arriving at Westchester County Airport (HPN), travelers can easily reach White Plains, Manhattan, Yonkers, Stamford (CT), Greenwich (CT), the Hudson Valley, and northern New Jersey; HPN is a convenient gateway for regional business and leisure travel in October. Plan ground transport ahead of time to maximize your time at nearby attractions and seasonal fall activities.
Westchester County Airport (HPN) follows current federal and local health guidelines; travelers arriving from Southwest Florida International Airport (RSW) should check the latest advisories before October travel. For smooth arrivals, review airline and airport health policies and plan for any documentation required by carriers or local authorities.
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October Events & Festivals Near Southwest Florida International Airport (RSW) and Westchester County (HPN)
October brings fall festivals, farmers markets, and Halloween activities in both Southwest Florida and Westchester County. In Fort Myers and Naples expect local arts festivals and seafood events, while Westchester and nearby New York City host film festivals, Halloween parades, and cultural events that can boost arrivals at Westchester County Airport (HPN). If traveling in October, check local event calendars and book flights and ground transport early to avoid sold-out hotels and peak fares. CTA: Review event dates and secure RSW to HPN travel plans now to avoid October crowding.
Best Time to Fly from Southwest Florida International Airport (RSW) to Westchester County Airport (HPN) in October
For October travel from Southwest Florida International Airport (RSW) to Westchester County Airport (HPN), the best time to book is 3–8 weeks in advance with travel midweek (Tuesday–Thursday) to secure lower fares. Avoid early October holiday weekends and book early if your travel coincides with major NYC events. Business travelers often prefer early-week departures and late-afternoon returns to maximize workdays; leisure travelers can take advantage of midweek price drops for weekend stays. CTA: Start monitoring fares now and book your preferred RSW to HPN October travel window.
Direct vs Connecting Flights: Southwest Florida International Airport (RSW) to Westchester County Airport (HPN)
Most RSW to HPN itineraries require at least one connection; while direct nonstop flights would be faster, they are uncommon on this route. Connecting flights allow more schedule flexibility and often lower fares, but increase the risk of missed connections during October travel if delays occur. When choosing a connection, pick a reliable carrier and aim for 60–90 minute connections in major hubs to balance speed and reliability. CTA: Compare connecting options and select flights with realistic layover times for your October trip.
Airline Comparison for Southwest Florida International Airport (RSW) to Westchester County Airport (HPN)
American Airlines and Delta commonly provide the most consistent one-stop service from Southwest Florida International Airport (RSW) to Westchester County Airport (HPN) via their hubs; JetBlue may offer alternative connections via New York hubs. American often routes through Charlotte or Philadelphia, while Delta commonly connects via Atlanta; evaluate baggage fees, loyalty benefits, and connection reliability when choosing. For October travel, prioritize carriers with strong on-time records and comfortable connection airports to minimize disruption. CTA: Compare fares and schedules across carriers to pick the best October RSW to HPN option for your trip.
Seasonal Travel Tips for October: Southwest Florida International Airport (RSW) to Westchester County Airport (HPN)
Pack layered clothing for October trips from Southwest Florida International Airport (RSW) to Westchester County Airport (HPN) since temperatures can range from mild Florida warmth to cool Northeastern fall weather. Check weather forecasts for both origin and destination before departure, and allow flexible connection times in case of localized delays. For cost savings, travel midweek, enroll in frequent flyer programs, and use credit-card perks for lounge access or priority boarding. CTA: Prepare smart for your October RSW to HPN trip by booking early and packing for varied fall conditions.
Flight Time & Schedules for Southwest Florida International Airport (RSW) to Westchester County Airport (HPN)
There are generally no nonstop flights from Southwest Florida International Airport (RSW) to Westchester County Airport (HPN); expect total travel times of 4.5–7 hours depending on the connection hub and layover length. Morning departures from RSW with an afternoon arrival at HPN are common when connecting through Charlotte (CLT) or Philadelphia (PHL). For October travel, choose tighter connection windows of 45–90 minutes at major hubs to balance speed and reliability while leaving buffer for delays. CTA: Check current airline schedules and select flight times that align with your October itinerary needs.
Cheap Flights: Southwest Florida International Airport (RSW) to Westchester County Airport (HPN) in October
To find cheap flights from Southwest Florida International Airport (RSW) to Westchester County Airport (HPN) in October, search flexible dates, target Tuesdays and Wednesdays, and avoid Columbus Day weekend when rates can spike. Use fare alerts and set broad search windows including nearby airports such as Tampa or Miami for outbound alternatives. Consider mixed-carrier itineraries and look for last-minute sales in late summer for October travel. CTA: Sign up for alerts now and compare RSW to HPN prices across multiple search engines to capture limited-time October deals.