Cheap flights To Winthrop (BOS) from $51

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Cheap Flights to Winthrop from $51 One Way, $110 Round Trip

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Thu, Jan 21 - Sun, Jan 24
SFB
Orlando Sanford Intl.
PSM
Portsmouth Intl.
$110 Roundtrip, found 12 hours ago
$110
Roundtrip
found 12 hours ago
Select Allegiant Air flight, departing Thu, Jan 21 from Orlando Sanford Intl. to Portsmouth Intl., returning Sun, Jan 24, priced at $110 found 12 hours ago
Sat, Oct 31 - Sat, Nov 7
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$112 Roundtrip, found 3 days ago
$112
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Sat, Oct 31 from Orlando Intl. to Portsmouth Intl., returning Sat, Nov 7, priced at $112 found 3 days ago
Sat, Oct 3 - Sat, Nov 7
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$113 Roundtrip, found 3 days ago
$113
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Sat, Oct 3 from Orlando Intl. to Portsmouth Intl., returning Sat, Nov 7, priced at $113 found 3 days ago
Sat, Oct 17 - Sat, Oct 24
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$118 Roundtrip, found 6 days ago
$118
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Sat, Oct 17 from Orlando Intl. to Portsmouth Intl., returning Sat, Oct 24, priced at $118 found 6 days ago
Sun, Jan 10 - Sun, Jan 17
SFB
Orlando Sanford Intl.
PSM
Portsmouth Intl.
$120 Roundtrip, found 5 days ago
$120
Roundtrip
found 5 days ago
Select Allegiant Air flight, departing Sun, Jan 10 from Orlando Sanford Intl. to Portsmouth Intl., returning Sun, Jan 17, priced at $120 found 5 days ago
Thu, Nov 12 - Thu, Nov 19
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$122 Roundtrip, found 4 days ago
$122
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Nov 12 from Raleigh - Durham Intl. to Portsmouth Intl., returning Thu, Nov 19, priced at $122 found 4 days ago
Sat, Oct 31 - Sat, Nov 7
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$122 Roundtrip, found 7 hours ago
$122
Roundtrip
found 7 hours ago
Select Breeze Airways flight, departing Sat, Oct 31 from Orlando Intl. to Portsmouth Intl., returning Sat, Nov 7, priced at $122 found 7 hours ago
Sat, Oct 10 - Sat, Oct 24
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$123 Roundtrip, found 5 days ago
$123
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Sat, Oct 10 from Orlando Intl. to Portsmouth Intl., returning Sat, Oct 24, priced at $123 found 5 days ago
Sat, Oct 24 - Sat, Oct 31
MCO
Orlando Intl.
BOS
Logan Intl.
$126 Roundtrip, found 2 days ago
$126
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, Oct 24 from Orlando Intl. to Logan Intl., returning Sat, Oct 31, priced at $126 found 2 days ago
Sat, Oct 24 - Sat, Oct 31
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$128 Roundtrip, found 8 hours ago
$128
Roundtrip
found 8 hours ago
Select Breeze Airways flight, departing Sat, Oct 24 from Orlando Intl. to Portsmouth Intl., returning Sat, Oct 31, priced at $128 found 8 hours ago

Winthrop Flight Information

Traveling To
Winthrop
Destination Airport IATA Code
BOS
Number of Airlines Serving
Airlines
Breeze Airways, Allegiant Air, Frontier Airlines
Flight Price
$110
Earliest Departing Flight
Latest Departing Flight

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Winthrop economy flight packages

Price found within the past 48 hours. Click for updated prices.
Furnished Apartment Near Longwood
3.0-star property

Furnished Apartment Near Longwood

Oct 23 - Oct 28

5 night stay

New York (NYC) to Boston (BOS)

JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $1,420, price is now $1,063 per person
$1,063
per person
found 11 hours ago
Mandarin Oriental, Boston
5.0-star property

Mandarin Oriental, Boston

Nov 4 - Nov 7

3 night stay

Chicago (ORD) to Boston (BOS)

Delta • Coach

Boston (BOS) to Chicago (ORD)

Frontier Airlines • Coach
Save 100% on your flight
Price was $1,510, price is now $1,091 per person
$1,091
per person
found 1 day ago
Boston Harbor Hotel
5.0-star property

Boston Harbor Hotel

Nov 5 - Nov 8

3 night stay

Detroit (DTW) to Boston (BOS)

United • Non-stop roundtrip • Coach
Price was $1,689, price is now $1,268 per person
$1,268
per person
found 1 day ago
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Winthrop first class flight packages

Price found within the past 48 hours. Click for updated prices.
Fairmont Copley Plaza, Boston
4.5-star property

Fairmont Copley Plaza, Boston

9/10 Wonderful! (1,317 reviews)

Oct 16 - Oct 18

2 night stay

Newark Liberty Intl. Airport (EWR) to Boston (BOS)

Delta • FirstClass

Boston (BOS) to Newark Liberty Intl. Airport (EWR)

United • FirstClass
Price was $1,529, price is now $1,157 per person
$1,157
per person
found 1 day ago
Bring back sliced smoked salmon in Gold Lounge

Reviewed on Sep 12, 2026

Boston Harbor Hotel
5.0-star property

Boston Harbor Hotel

9.8/10 Exceptional! (1,014 reviews)

Oct 16 - Oct 18

2 night stay

Newark Liberty Intl. Airport (EWR) to Boston (BOS)

Delta • FirstClass

Boston (BOS) to Newark Liberty Intl. Airport (EWR)

United • FirstClass
Price was $1,907, price is now $1,447 per person
$1,447
per person
found 1 day ago
Quiet tasteful and amazing views

Reviewed on Sep 12, 2026

The Godfrey Hotel Boston
4.0-star property

The Godfrey Hotel Boston

9.6/10 Exceptional! (5,211 reviews)

Oct 18 - Oct 21

3 night stay

Chicago (ORD) to Boston (BOS)

American Airlines • FirstClass

Boston (BOS) to Chicago (ORD)

Frontier Airlines • FirstClass
Price was $1,695, price is now $1,401 per person
$1,401
per person
found 3 hours ago

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See all available trips from Newark Liberty Intl. Airport to Winthrop
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Winthrop

When you plan to buy tickets for flights to Winthrop, you don’t have to look any further than Orbitz! We offer bargain rates and low fares on thousands of flights.

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Convenient Travel Planning Services

If you like the ease of making your travel plans on the move, you’ll love the free Orbitz apps for iPhones, iPads, and Android devices. You can use these apps to review your travel reservations or make a change to your itinerary. Orbitz also offers additional travel assistance such as free mobile alerts that keep you up-to-date about sudden changes to your upcoming flights. You can also browse Orbitz easily on your smartphone by using the mobile version of the website to find budget Winthrop flights.

Frequently asked questions

Which airlines fly to Winthrop?
With 20 airlines servicing Logan Intl. Airport (BOS), the main entry point to Winthrop, you have plenty of choice. Find a terrific deal among these top international airlines that fly in and out of this city:

  • JetBlue - 175 flights to Winthrop per month
  • Delta - 158 flights to Winthrop per month
  • Air Canada - 151 flights to Winthrop per month

What is the best airport to fly to in Winthrop?
Logan Intl. Airport (BOS) is the entry point to the city, so the only decision you need to make will be the aisle seat or the window seat. Downtown Winthrop is around 2 miles away and where many visitors kick off their adventure.
How much is a flight to Winthrop?
The cost for a return flight to Winthrop this week fluctuated between $110 and $128. If you were flying one-way out of Orlando (MCO), you could have snapped up fares from as low as $51.
How to book the cheapest flight to Winthrop?
Picking up cheap flights to Winthrop is as easy as booking your ticket with Orbitz. But if you want to make sure you're walking away with the best flight deals around, here are a few tips your budget will love:

  • Consider departing from or arriving at alternative airports to save extra cash. Enter your preferred departure and arrival points in the form fields, then choose the 'Nearby airports' function below. It will list the available options.
  • Similarly, click on the 'Show flexible dates' option to compare the fares on days around your selected departure. You may be able to find cheaper flight deals if your travel plans are flexible.
  • Hit 'Show options' to refine your search results. You can pick your preferred airline and seating class here. Under 'Sort & Filter' to the left, you can even select whether you want to fly in the morning, afternoon or evening.
  • Lock in your fare as soon as you've figured out your travel dates. While you can get lucky once in a while, airfares rarely drop in price as your date of departure nears.
  • Combine your hotels, flights and car rental into a package deal and unlock great discounts. Save your dollars for things that really excite you, like exploring Winthrop.
  • If it's an option, avoid traveling in the busy season. Airfares are often at their highest during school breaks, summer and around other vacation times like Easter, Thanksgiving and Christmas.

How long is a flight to Winthrop?
Flight durations depend on where you're leaving from, whether that's the East Coast, the West Coast or someplace else. Listed below are three of the most popular routes to Winthrop and average flight times:

  • Washington, DC (DCA-Ronald Reagan Washington National) to Logan Intl. Airport (BOS) - 1 hour and 44 minutes
  • New York, NY (LGA-LaGuardia) to Logan Intl. Airport (BOS) - 1 hour and 34 minutes
  • New York, NY (JFK-John F. Kennedy Intl.) to Logan Intl. Airport (BOS) - 1 hour and 17 minutes

What is the best time to book a flight to Winthrop?
Purchase your seats to Winthrop in January. This is a fantastic month for bargain prices, followed by February and August. Find cheap flights and enjoy your dream getaway with Orbitz.
What day of the week is the cheapest to book a flight to Winthrop?
When it comes to cheap fares to Winthrop, the best days to make a booking are generally Tuesdays, Wednesdays and Saturdays. An unbeatable flight deal is just a few clicks away with Orbitz.
What is the cheapest day of the week to fly to Winthrop?
Everyone enjoys a good deal, so we suggest flying out early in the week for cheap flights to Winthrop. Orbitz data from 2020 suggests you can secure the best deals on flights taking off on Mondays. Tuesday is the next most affordable day, while Saturdays are likely to cost a bundle. Many passengers prefer to travel when the working week is over, so leave those Saturdays for catching up with friends.
What is the cheapest month to fly to Winthrop?
We won't keep you in suspense — according to Orbitz data, August is generally the most affordable month to fly. Ideal for those who want a weekend getaway or simply escape from it all before the weather changes. The costliest time to fly is in the middle of summer, with airfares peaking in June.
Which airlines allow free cancellation?
We know that plans can change and flexibility is important. That's why you can easily search for flights that have free cancellation and no change fees on Orbitz. Just click on "Filter by flexible change policies" and we'll find you fares more flexible than a lip balm left in the sun!
What do I need for the flight to Winthrop?
Nothing's more enjoyable than jetting to a new place, but it's good to be prepared. The following handy tips will help get your trip started on the right foot:

  • Your travel documents are the most important items you'll need to have with you on your flight. To avoid any problems while checking in, make sure that the information displayed on your ticket is the same as on your government-issued photo ID.
  • To keep you amused on your short trip to Winthrop, download your favorite songs or restock the audiobook library on your smartphone. Food can also be a tasty distraction while in the air, so take a snack.
  • Whatever the weather outside, plane cabins can get cold. Bring a light jacket on board to keep yourself comfortable.

How many direct flights are there to Winthrop?
There are 1,287 flights that travel straight to Winthrop every month, which means you won't have to deal with irritating stopovers. Lock in a fare with JetBlue Airways or Delta Air Lines and then kick back, relax and enjoy the flight. American Airlines, Cape Air, United Airlines and Southwest Airlines also operate nonstop flights to Winthrop.
How do I get cheap first-class/business deals to Winthrop?
Experienced travelers have a way of finding first or business-class fares to Winthrop without the astronomical price tag. Take a leaf out of their book with these handy tips:

  • Being flexible isn't just a yoga thing. Avoid locking in your travel dates so you can pick up more affordable airfares when a big sale drops.
  • Budget airlines offer business-class seats at a fraction of the normal price. Ditch the full-service carriers and consider these cheaper options.
  • Make a bid for an upgrade. Some carriers hold online auctions that let you offer a price for a seat at the front of the plane. You may also be able to upgrade with points earned through a flight loyalty scheme.

How to get into Winthrop from the airport?
Be the captain of your own adventure with a Logan Intl. Airport (BOS) car rental. Arrive at Logan Intl. Airport (BOS) and then pick up a ride from one of the outlets on-site. Enterprise and Advantage Rent-A-Car both have a large selection of vehicles to choose from. Once the keys are in your hand, you'll need to travel about 2 miles to the east to make it to the bustle of central Winthrop. Renting a vehicle from the city center is another popular option with great deals available from Winthrop car rentals.
What is the best time to go to Winthrop?
Winthrop is a lively place in April, May and June. If you plan to head there during these months, it would be wise to book ahead of time to ensure you snap up the best deals. Like to know what summertime's like in Winthrop? Average daily temperatures generally range between 65 ºF and 80 ºF. Like many destinations in the Northern Hemisphere, summer starts June 20 here.

More to Explore

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.