Cheap flights To Winthrop (BOS) from $47

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

Cheap Flights to Winthrop from $47 One Way, $84 Round Trip

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

Thu, Nov 5 - Sun, Nov 8
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, Nov 5 from Orlando Sanford Intl. to Portsmouth Intl., returning Sun, Nov 8, priced at $84 found 4 days ago
Thu, Jan 7 - Sun, Jan 10
SFB
Orlando Sanford Intl.
PSM
Portsmouth Intl.
$85 Roundtrip, found 2 days ago
$85
Roundtrip
found 2 days ago
Select Allegiant Air flight, departing Thu, Jan 7 from Orlando Sanford Intl. to Portsmouth Intl., returning Sun, Jan 10, priced at $85 found 2 days ago
Sun, Jan 10 - Sun, Jan 17
SFB
Orlando Sanford Intl.
PSM
Portsmouth Intl.
$92 Roundtrip, found 21 hours ago
$92
Roundtrip
found 21 hours ago
Select Allegiant Air flight, departing Sun, Jan 10 from Orlando Sanford Intl. to Portsmouth Intl., returning Sun, Jan 17, priced at $92 found 21 hours ago
Sun, Nov 1 - Sun, Nov 8
SFB
Orlando Sanford Intl.
PSM
Portsmouth Intl.
$95 Roundtrip, found 2 days ago
$95
Roundtrip
found 2 days ago
Select Allegiant Air flight, departing Sun, Nov 1 from Orlando Sanford Intl. to Portsmouth Intl., returning Sun, Nov 8, priced at $95 found 2 days ago
Thu, Jan 14 - Sun, Jan 17
SFB
Orlando Sanford Intl.
PSM
Portsmouth Intl.
$100 Roundtrip, found 2 days ago
$100
Roundtrip
found 2 days ago
Select Allegiant Air flight, departing Thu, Jan 14 from Orlando Sanford Intl. to Portsmouth Intl., returning Sun, Jan 17, priced at $100 found 2 days ago
Sun, Nov 1 - Thu, Nov 5
SFB
Orlando Sanford Intl.
PSM
Portsmouth Intl.
$102 Roundtrip, found 1 day ago
$102
Roundtrip
found 1 day ago
Select Allegiant Air flight, departing Sun, Nov 1 from Orlando Sanford Intl. to Portsmouth Intl., returning Thu, Nov 5, priced at $102 found 1 day ago
Thu, Feb 4 - Sun, Feb 7
SFB
Orlando Sanford Intl.
PSM
Portsmouth Intl.
$110 Roundtrip, found 6 days ago
$110
Roundtrip
found 6 days ago
Select Allegiant Air flight, departing Thu, Feb 4 from Orlando Sanford Intl. to Portsmouth Intl., returning Sun, Feb 7, priced at $110 found 6 days ago
Thu, Dec 10 - Sun, Dec 13
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, Dec 10 from Raleigh - Durham Intl. to Portsmouth Intl., returning Sun, Dec 13, priced at $112 found 1 day ago
Thu, Dec 10 - Sun, Dec 13
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$117 Roundtrip, found 1 day ago
$117
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Dec 10 from Raleigh - Durham Intl. to Portsmouth Intl., returning Sun, Dec 13, priced at $117 found 1 day ago
Sat, Jan 16 - Sat, Jan 23
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$117 Roundtrip, found 5 hours ago
$117
Roundtrip
found 5 hours ago
Select Breeze Airways flight, departing Sat, Jan 16 from Orlando Intl. to Portsmouth Intl., returning Sat, Jan 23, priced at $117 found 5 hours ago

Winthrop Flight Information

Traveling To
Winthrop
Destination Airport IATA Code
BOS
Number of Airlines Serving
Airlines
Allegiant Air, Breeze Airways
Flight Price
$84
Earliest Departing Flight
Latest Departing Flight

Book Your Flight & Hotel Together & Save

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

Sep 8 - Sep 13

5 night stay

Tampa (TPA) to Boston (BOS)

Delta • Roundtrip • Coach
Save 100% on your flight
Price was $1,476, price is now $1,037 per person
$1,037
per person
found 16 hours ago
Iris Hotel Boston
4.0-star property

Iris Hotel Boston

Sep 12 - Sep 19

7 night stay

Los Angeles (LAX) to Boston (BOS)

JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $1,930, price is now $1,146 per person
$1,146
per person
found 1 day ago
Good Hotels Boston
2.0-star property

Good Hotels Boston

Sep 2 - Sep 7

5 night stay

Los Angeles (LAX) to Boston (BOS)

United • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,666, price is now $1,137 per person
$1,137
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from Tampa to Winthrop
View all trips

Winthrop first class flight packages

Price found within the past 48 hours. Click for updated prices.
AutoCamp Cape Cod
4.0-star property

AutoCamp Cape Cod

9.2/10 Wonderful! (362 reviews)

Aug 29 - Sep 1

3 night stay

Chicago (ORD) to Boston (BOS)

American Airlines • Roundtrip • FirstClass
Price was $1,386, price is now $1,301 per person
$1,301
per person
found 15 hours ago

Sea Crest Beach Resort
3.5-star property

Sea Crest Beach Resort

7.8/10 Good! (359 reviews)

Aug 29 - Sep 1

3 night stay

Chicago (ORD) to Boston (BOS)

American Airlines • Roundtrip • FirstClass
Price was $1,612, price is now $1,493 per person
$1,493
per person
found 15 hours ago

The Club at New Seabury
3.5-star property

The Club at New Seabury

9/10 Wonderful! (362 reviews)

Aug 29 - Sep 1

3 night stay

Chicago (ORD) to Boston (BOS)

American Airlines • Roundtrip • FirstClass
Price was $2,426, price is now $2,292 per person
$2,292
per person
found 15 hours ago

Don't see what you're looking for?
See all available trips from Chicago to Winthrop
View all trips

Winthrop

Orbitz uses cutting edge mobile technology to help get you the best deals on Winthrop flights. We offer guaranteed low prices on air tickets that can be combined with hotels and car rentals to save you even more money.

Find Cheap Winthrop Flights And Hotel Rooms Using Our Mobile App

Orbitz not only guarantees low prices for flights to Winthrop, we also offer Mobile Steals on our Orbitz on the Go mobile app where you can find great mobile-only deals on hotel rooms in the area.

Use the Orbitz Flight Matrix To Save Big On Car Rental

Discount flights to Winthrop can be combined with car rental to get you additional savings. Just use our Flight Matrix to see how your budget air ticket can be combined with a car rental to make your trip not only inexpensive but also more convenient.

Use Multiple Airlines To Ensure You Get The Best Deal

Orbitz allows you to use multiple airlines for flights to Winthrop. By using a combination of airlines for discount flights you are guaranteed to get the lowest fares each way and get the schedule that is most convenient for you.

Store Your Frequent Flyer Information on Orbitz For Easy Access

Booking with Orbitz will still allow you to apply miles for flights to Winthrop to your frequent flyer program. Not only that, but your frequent flyer information will be safely stored on our website, so it will be easy to access the next time you book a discount air ticket with Orbitz.

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 $84 and $117. 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.