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Boston to Westchester 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

Boston and Westchester airports and terminals

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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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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Cheap flights from Boston to Westchester

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$539
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Highlighted price = Cheapest round-trip flights

Prices are round trip per person (conditions apply)

Featured Westchester Airport Hotels

Hotel only $183

Doral Arrowwood

4 stars
3.8 / 5 8 reviews

975 Anderson Hill Rd Map

Save 10% on your stay

The Doral Arrowwood consists of 373 guest rooms and is located on 114 wooded acres in a quiet corner of Westchester County.... More

Hotel only $97

La Quinta Inn & Suites Armonk Westchester County Airport

3 stars
3.2 / 5 90 reviews

94 Business Park Dr Map

Nestled in peaceful Westchester County, our full-service La Quinta Inn & Suites Armonk Westchester County Airport is HERE FOR YOU!... More

Hotel only $179

HYATT house White Plains

3 stars
4.5 / 5 42 reviews

101 Corporate Park Dr Map

Save 30% on your stay

The HYATT house White Plains is a159-room all suite hotel located in suburban Westchester. Our 1-bed and 2-bed/2-bath suites feature fully-equipped, full-size kitchens, ice-maker, sleeper sofa,... More

Hotel only $134

Renaissance Westchester Hotel

4 stars
4.0 / 5 59 reviews

80 Map

Rate includes breakfast

Delight in the resort atmosphere of Renaissance Westchester Hotel in White Plains, NY, nestled on 30 acres of scenic countryside in Westchester County.... More

Hotel only $149

Hilton Westchester

3 stars
3.7 / 5 33 reviews

699 Westchester Avenue Map

Rate includes Breakfast

The Hilton Westchester hotel, located in the New York City suburb of Rye, NY, is just 10 minutes east of White Plains, NY in Westchester County and eight miles from Westchester County Airport... More

Hotel only $143

Crowne Plaza WHITE PLAINS-DOWNTOWN

4 stars
4.0 / 5 59 reviews

66 Hale Avenue Map

...The Top Choice of Hotels in White Plains, NY Crowne Plaza® is located in downtown White Plains, the heart of Westchester County.... If youre looking for hotels near Westchester Airport, we are... More

October

Lowest roundtrip airfare in October from Boston to Westchester

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, Oct 7 Boston (BOS) Westchester (HPN) Cape Air $539
Earn $5.39
Return Wed, Oct 8 Westchester (HPN) Boston (BOS) Cape Air
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November

Cheapest weekend flights in November from Boston to Westchester

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Nov 13 Boston (BOS) Westchester (HPN) Cape Air $519
Earn $5.19
Return Sun, Nov 16 Westchester (HPN) Boston (BOS) Cape Air

Lowest roundtrip airfare in November from Boston to Westchester

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Nov 13 Boston (BOS) Westchester (HPN) Cape Air $519
Earn $5.19
Return Sun, Nov 16 Westchester (HPN) Boston (BOS) Cape Air
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Flights to Westchester

Boston Logan International Airport

The Boston Logan International Airport is located at 1 Harborside Drive, approximately four miles from downtown Boston. Numerous airlines service the airport, including US Airways, Virgin America, JetBlue and British Airways. Orbitz.com can help you find cheap flights from Boston. The website searches and displays your flight choices, so you can book one with a cheap rate.

Parking and Transportation

If you need to leave your car at the airport while you travel, there are several parking lots available. Most of the lots cost $27 per day to park; however, the airport does have an economy parking lot that offers long-term parking for $18 per day. There are shuttles that run from all of the parking lots to the airport terminals. The subway runs from downtown Boston to the airport. The trip takes between 35 and 45 minutes and costs $2. Taxicab services from downtown Boston to the airport cost between $25 and $45, depending on the length of the trip. The Orbitz.com website has the tools you need to reserve a rental car at your destination. This way, you don't have to wait at the airport. Your car will be ready for you when you arrive.

Dining at the Airport

When you use Orbitz.com to book cheap flights from Boston, you don't have to worry about your travel arrangements. This gives you plenty of time to grab a quick meal before you board your plane. The airport has a variety of dining options available, including Johnny Rockets, Vineyard Grille and Wolfgang Puck Gourmet Express.

Airports in Westchester, NY

When you search for domestic flights to Westchester, NY, on Orbitz.com, you're certain to find the best possible deal. Westchester County is serviced by the Westchester County Airport, a small facility located about four miles outside White Plains. Twelve commercial airlines maintain regular flights to and from the airport, including Delta, jetBlue, American Airlines and United.

Transportation From the Airport

There are several ways to get from the airport into the surrounding county. Taxis and limousines offer quick access to nearby hotels. Because of the airport's central location within the county, you're never more than a few minutes away from lodging or attractions. The Bee-Line bus system also provides fast transport to local destinations, as well as connections to the MTA Metro-North Railroad and a direct path into New York City.

Weather in Westchester

The weather in Westchester varies depending on how near you are to the coast. Winters are cold and snowy, with lows dipping well below freezing. Summertime is hot, especially inland, where temperatures can soar into the 90s. Closer to the coast, refreshing ocean breezes keep the temperature more moderate.

Things to Do in Westchester

The Caramoor Center for Music and the Arts hosts an amazing 7-week outdoor festival each summer. Classical music and jazz fill the lush gardens with beautiful music. The nearby Katonah Museum of Art offers compelling exhibitions throughout the year. Also at the museum, the Children's Learning Center offers free admission to families and is fun for all ages. Make sure you look for discounts when you search for flights to Westchester through Orbitz.com.