Cheap flights To Winthrop (BOS) from $47

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Cheap Flights to Winthrop from $47 One Way, $77 Round Trip

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

Thu, Jan 7 - Sun, Jan 10
SFB
Orlando Sanford Intl.
PSM
Portsmouth Intl.
$77 Roundtrip, found 5 days ago
$77
Roundtrip
found 5 days ago
Select Allegiant Air flight, departing Thu, Jan 7 from Orlando Sanford Intl. to Portsmouth Intl., returning Sun, Jan 10, priced at $77 found 5 days ago
Thu, Jan 7 - Sun, Jan 10
SFB
Orlando Sanford Intl.
PSM
Portsmouth Intl.
$84 Roundtrip, found 4 days ago
$84
Roundtrip
found 4 days ago
Select Allegiant Air flight, departing Thu, Jan 7 from Orlando Sanford Intl. to Portsmouth Intl., returning Sun, Jan 10, priced at $84 found 4 days ago
Thu, Jan 7 - Sun, Jan 10
SFB
Orlando Sanford Intl.
PSM
Portsmouth Intl.
$92 Roundtrip, found 18 hours ago
$92
Roundtrip
found 18 hours ago
Select Allegiant Air flight, departing Thu, Jan 7 from Orlando Sanford Intl. to Portsmouth Intl., returning Sun, Jan 10, priced at $92 found 18 hours ago
Thu, Jan 21 - Thu, Jan 28
SFB
Orlando Sanford Intl.
PSM
Portsmouth Intl.
$102 Roundtrip, found 5 days ago
$102
Roundtrip
found 5 days ago
Select Allegiant Air flight, departing Thu, Jan 21 from Orlando Sanford Intl. to Portsmouth Intl., returning Thu, Jan 28, priced at $102 found 5 days ago
Thu, Oct 29 - Sun, Nov 1
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$112 Roundtrip, found 1 day ago
$112
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Oct 29 from Raleigh - Durham Intl. to Portsmouth Intl., returning Sun, Nov 1, priced at $112 found 1 day ago
Thu, Oct 29 - Sun, Nov 1
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$117 Roundtrip, found 9 hours ago
$117
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Thu, Oct 29 from Raleigh - Durham Intl. to Portsmouth Intl., returning Sun, Nov 1, priced at $117 found 9 hours ago
Sat, Jan 16 - Sat, Jan 23
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$117 Roundtrip, found 2 days ago
$117
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sat, Jan 16 from Orlando Intl. to Portsmouth Intl., returning Sat, Jan 23, priced at $117 found 2 days ago
Thu, Oct 29 - Sun, Nov 1
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$122 Roundtrip, found 9 hours ago
$122
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Thu, Oct 29 from Raleigh - Durham Intl. to Portsmouth Intl., returning Sun, Nov 1, priced at $122 found 9 hours ago
Sat, Oct 31 - Sun, Nov 8
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$126 Roundtrip, found 4 days ago
$126
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Sat, Oct 31 from Orlando Intl. to Portsmouth Intl., returning Sun, Nov 8, priced at $126 found 4 days ago
Sat, Sep 19 - Sat, Oct 10
MCO
Orlando Intl.
BOS
Logan Intl.
$127 Roundtrip, found 4 days ago
$127
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, Sep 19 from Orlando Intl. to Logan Intl., returning Sat, Oct 10, priced at $127 found 4 days ago

Winthrop Flight Information

Traveling To
Winthrop
Destination Airport IATA Code
BOS
Number of Airlines Serving
Airlines
Allegiant Air, Breeze Airways, Frontier Airlines
Flight Price
$77
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.
Iris Hotel Boston
4.0-star property

Iris Hotel Boston

Sep 23 - Sep 30

7 night stay

Dallas (DAL) to Boston (BOS)

Southwest Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,435, price is now $1,447 per person
$1,447
per person
found 1 day ago
Furnished Apartment Near Longwood
3.0-star property

Furnished Apartment Near Longwood

Sep 23 - Sep 30

7 night stay

Dallas (DAL) to Boston (BOS)

Southwest Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,689, price is now $1,759 per person
$1,759
per person
found 1 day ago
Raffles Boston
5.0-star property

Raffles Boston

Sep 27 - Oct 3

6 night stay

Dallas (DFW) to Boston (BOS)

American Airlines • Coach

Boston (BOS) to Dallas (DFW)

Frontier Airlines • Coach
Save 100% on your flight
Price was $5,254, price is now $3,656 per person
$3,656
per person
found 1 day ago
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Winthrop premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
The Concord Hotel
2.0-star property

The Concord Hotel

7/10 Good! (10 reviews)

Sep 24 - Sep 27

3 night stay

Chicago (ORD) to Boston (BOS)

JetBlue Airways • PremiumEconomy

Boston (BOS) to Chicago (ORD)

Frontier Airlines • PremiumEconomy
Price was $1,233, price is now $1,012 per person
$1,012
per person
found 1 hour ago
Very good location! And clean building and the room. Check in process definitely needs to have more details - specifically your room#, as its a 4story building Communication was on top, they are really looking forward to solve your request.

Reviewed on Aug 4, 2026

The Charles Hotel
5.0-star property

The Charles Hotel

9.4/10 Exceptional! (1,006 reviews)

Sep 24 - Sep 27

3 night stay

Chicago (ORD) to Boston (BOS)

JetBlue Airways • PremiumEconomy

Boston (BOS) to Chicago (ORD)

Frontier Airlines • PremiumEconomy
Price was $1,415, price is now $1,091 per person
$1,091
per person
found 1 hour ago

Arcadian Hotel
3.5-star property

Arcadian Hotel

8/10 Very Good! (4,364 reviews)

Sep 24 - Sep 27

3 night stay

Chicago (ORD) to Boston (BOS)

JetBlue Airways • PremiumEconomy

Boston (BOS) to Chicago (ORD)

Frontier Airlines • PremiumEconomy
Price was $1,292, price is now $1,058 per person
$1,058
per person
found 1 hour ago

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Winthrop first class flight packages

Price found within the past 48 hours. Click for updated prices.
Sesuit Harbor House
3.0-star property

Sesuit Harbor House

9.6/10 Exceptional! (196 reviews)

Sep 13 - Sep 18

5 night stay

Dallas (DFW) to Boston (BOS)

Delta • Roundtrip • FirstClass
Price was $2,244, price is now $1,709 per person
$1,709
per person
found 22 hours ago
The Sesuit Harbor House is awesome. Has a very Cape Cod feel, the owners are excellent very attentive and have done an awesome job with this property. There is a beautiful fire pit, pool, nice outside areas to eat and relax and they also have goats! I highly recommend, close to dining and beaches as well.

Reviewed on Aug 1, 2026

The Charles Hotel
5.0-star property

The Charles Hotel

9.4/10 Exceptional! (1,006 reviews)

Sep 25 - Sep 29

4 night stay

Sacramento (SMF) to Boston (BOS)

American Airlines • Non-stop roundtrip • FirstClass
Price was $2,439, price is now $1,996 per person
$1,996
per person
found 1 day ago

Good Hotels Boston
2.0-star property

Good Hotels Boston

8/10 Very Good! (55 reviews)

Sep 25 - Sep 28

3 night stay

Sacramento (SMF) to Boston (BOS)

American Airlines • Non-stop roundtrip • FirstClass
Price was $2,580, price is now $1,892 per person
$1,892
per person
found 1 day ago
This was a very clean and well-looked after property, and the staff went out of their way to check everything was in order.

Reviewed on May 23, 2026

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Winthrop

If you are looking for discount prices on flights to Winthrop then look no further than Orbitz. With some of the best deals available, cutting-edge technology, and great customer service, Orbitz makes booking Winthrop flights easy and affordable.

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The Complete Package

Orbitz makes it stress-free to book Winthrop flights, and we can also help you figure out the rest of your trip just as easily. If you need great deals on hotels and car rentals following your flights to Winthrop, just add the details to your booking and search for the cheapest deals out there. And why waste time lining up for admission to attractions and events? With Orbitz, you can book tickets in advance and waltz straight in.

Low Price Guarantee

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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 $77 and $127. If you were flying one-way out of Orlando (SFB), you could have snapped up fares from as low as $47.
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.