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Westchester to Boston Flights

Flight only Hotel only Flight + Hotel

Flight type

Round-trip One-way
Age of children at time of trip

We will search for applicable airfare discounts. Must have 1 adult for each infant in lap

Selected fares from Westchester to Boston

Departure Arrival Travel dates Round-trip
HPN BOS Wed, Dec 31 - Sun, Jan 4 $398
HPN BOS Sat, Oct 18 - Tue, Oct 21 $552
HPN BOS Thu, Oct 30 - Sat, Nov 1 $697

Westchester and Boston airports and terminals

Airports in Westchester NY, US
map of airports in Westchester
  • 1

    JFK Airport (JFK)

    Distance from City Center: 29.7 miles

  • 2

    LaGuardia Airport (LGA)

    Distance from City Center: 22 miles

  • 3

    Newark Airport (EWR)

    Distance from City Center: 35.7 miles

  • 4

    Stewart (SWF)

    Distance from City Center: 36.7 miles

  • 5

    Danbury Airport (DXR)

    Distance from City Center: 25 miles

  • 6

    New Haven Airport (HVN)

    Distance from City Center: 44.6 miles

  • 7

    Westchester County Airport (HPN)

    Distance from City Center: 0.1 miles

  • 8

    Municipal (MMU)

    Distance from City Center: 42 miles

  • 9

    Long Island Macarthur (ISP)

    Distance from City Center: 36.7 miles

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Airports in Boston MA, US
map of airports in Boston
  • 1

    Boston Logan Airport (BOS)

    Distance from City Center: 3 miles

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Cheap flights from Westchester to Boston

Sun Mon Tue Wed Thu Fri Sat
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$494
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$494
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Highlighted price = Cheapest round-trip flights

Prices are round trip per person (conditions apply)

Featured Boston Airport Hotels

Hotel only $259

Hilton Boston Logan Airport

4 stars
4.2 / 5 190 reviews

One Hotel Drive Map

The Hilton Boston Logan Airport beckons weary vacationers with its illuminated 85-foot-tall spire, connected to the Logan Airport (BOS) by covered skywalk, but with soundproofed rooms to keep... More

Hotel only $239

Hyatt Boston Harbor

4 stars
4.2 / 5 143 reviews

101 Harborside Dr Map

Valet Parking For 1 vehicle up to 4 nights

...With a location close to Boston's Logan International Airport, the HYATT Boston Harbor is popular with both holidaymakers and business visitors.... More

Hotel only $215

Embassy Suites Boston - at Logan Airport

3 stars
3.9 / 5 83 reviews

207 Porter Street Map

Free cooked-to-order breakfast, Evening Reception

Airport-adjacent hotel with indoor pool and easy access to Boston The AAA three diamond-rated Embassy Suites Boston at Logan Airport offers a convenient location, especially for quick trips in and... More

Hotel only $239

Courtyard by Marriott Boston Logan Airport

3 stars
3.9 / 5 84 reviews

225 William F. McClellan Highway Map

Rate includes breakfast

...Contemporary hotel with free airport shuttle a mile from Logan Airport.... Courtyard by Marriott Boston Logan Airport surprises guests with modern, luxurious accommodations at affordable rates.... More

Hotel only $169

Suburban Extended Stay Logan Airport

2 stars
3.5 / 5 78 reviews

312 Shirley Street Map

...Limited airport shuttle by advance request only.... More

Hotel only $278

The Westin Boston Waterfront

4 stars
4.1 / 5 100 reviews

425 Summer Street Map

Save 40% on your stay

...Take the T train to city financial district, The Loop, or hop aboard an on-call water taxi at Fan Pier or Liberty Wharf when you're headed the three miles to Logan International Airport (BOS),... More

October

Cheapest weekend flights in October from Westchester to Boston

Travel dates Departure Arrival Stops: Round-trip
Leave Fri, Oct 17 Westchester (HPN) Boston (BOS) Cape Air $494
Earn $4.94
Return Sat, Oct 18 Boston (BOS) Westchester (HPN) Cape Air

Lowest roundtrip airfare in October from Westchester to Boston

Travel dates Departure Arrival Stops: Round-trip
Leave Fri, Oct 17 Westchester (HPN) Boston (BOS) Cape Air $494
Earn $4.94
Return Sat, Oct 18 Boston (BOS) Westchester (HPN) Cape Air
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November

Cheapest weekend flights in November from Westchester to Boston

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Nov 20 Westchester (HPN) Boston (BOS) Cape Air $519
Earn $5.19
Return Sat, Nov 22 Boston (BOS) Westchester (HPN) Cape Air

Lowest roundtrip airfare in November from Westchester to Boston

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Nov 20 Westchester (HPN) Boston (BOS) Cape Air $519
Earn $5.19
Return Sat, Nov 22 Boston (BOS) Westchester (HPN) Cape Air
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December

Lowest roundtrip airfare in December from Westchester to Boston

Travel dates Departure Arrival Stops: Round-trip
Leave Wed, Dec 31 Westchester (HPN) Boston (BOS) Cape Air $398
Earn $3.98
Return Sun, Jan 4 Boston (BOS) Westchester (HPN) Cape Air
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Flights to Boston

Westchester County Airport

Individuals looking for cheap flights from Westchester can easily find travel information at orbitz.com. The site has a special search engine that searches a variety of airlines at once in order to find cheap deals for the budget traveler. The Westchester County Airport serves the residents of Westchester and the surrounding area and is located approximately eight miles from downtown, on Cooney Hill Road. Seven airlines service the Westchester County Airport, including AirTran, American, Delta, United, JetBlue, US Airways and Cape Air. Orbitz.com books flights on the majority of these airlines.

Parking at the Airport

A 24-hour parking garage is available for travelers leaving Westchester. Parking in the lots is charged by the hour or by the day, and there are no discounts available for long-term use. Parking is limited at the airport; once the parking garage has reached capacity, travelers can use the overflow lots. The airport offers free shuttle service to and from the overflow lots. Individuals should make arrangements for drop-off and pick-up prior to the flight.

Transportation to the Airport

The Westchester County Airport offers a variety of travel options to the airport. Travelers can book car rental services using orbitz.com. Car rental fees vary depending on the type of vehicle rented, the length of rental time and the number of miles driven. Limos can be rented by the hour, and taxi services are available for a metered rate plus a drop-off fee. The Bee-Line bus provides services to the airport for a flat fee, and the MTA railroad is also available. Fees for rail travel depend on the distance traveled.

Restaurants at Westchester County Airport

The Skytop Restaurant provides both breakfast menu items and coffee, and the Coffee Shop provides a variety of muffins, doughnuts and coffee items. Orbitz.com can help make finding cheap flights from Westchester easy.

Boston Airport Information

Visitors to Boston usually fly into Logan International Airport, located roughly three miles across the harbor from downtown Boston. When you book flights to Boston through Orbitz.com, you will be able to choose from one of the many major domestic and international air passenger carriers that service the airport.

Ground Transportation in Boston

Logan Express bus service runs nonstop from Logan to Braintree, Framingham, Woburn and Peabody. For travel to all areas of Boston, take the MBTA's blue line subway service or silver line bus service. To get a view of Boston from the water, take the MBTA ferry to the commuter boat terminal in Quincy. A taxi from the airport to the downtown area should only cost you around $20, but if you have used Orbitz.com to book and purchase cheap tickets, your savings might be enough to warrant renting a car while you are there.

Boston Area Weather Information

Summers in Boston are beautiful, with average temperatures ranging from the mid-60s to the low 80s. Winters, however, can be brutal, with temperatures that can go from the low 20s to the mid-30s. When packing for your Boston trip, be sure to bring clothes that you can layer, and don't forget the warm jacket and snow boots if you plan to be there during the winter months.

What to Do in Boston

Boston is a mecca for history buffs. The Paul Revere House, King's Chapel Burying Ground, Bunker Hill monument, Old North Church and Old South Meeting House are must-see attractions. You should also plan to walk the Freedom Trail and spend a day at Faneuil Hall. Enjoy your trip to historic Boston, and remember to use Orbitz.com the next time you are looking for flights to Boston.