Cheap flights To Winthrop (BOS) from $72

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Cheap Flights to Winthrop from $72 One Way, $135 Round Trip

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

Tue, Jun 9 - Tue, Jun 9
DCA
Ronald Reagan Washington National
BOS
Logan Intl.
$135 Roundtrip, found 21 hours ago
$135
Roundtrip
found 21 hours ago
Select JetBlue Airways flight, departing Tue, Jun 9 from Ronald Reagan Washington National to Logan Intl., returning Tue, Jun 9, priced at $135 found 21 hours ago
Wed, Aug 12 - Wed, Aug 19
DCA
Ronald Reagan Washington National
BOS
Logan Intl.
$137 Roundtrip, found 2 hours ago
$137
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Wed, Aug 12 from Ronald Reagan Washington National to Logan Intl., returning Wed, Aug 19, priced at $137 found 2 hours ago
Wed, Jun 17 - Tue, Jun 23
DCA
Ronald Reagan Washington National
BOS
Logan Intl.
$140 Roundtrip, just found
$140
Roundtrip
just found
Select JetBlue Airways flight, departing Wed, Jun 17 from Ronald Reagan Washington National to Logan Intl., returning Tue, Jun 23, priced at $140 just found
Wed, Aug 12 - Wed, Aug 19
DCA
Ronald Reagan Washington National
BOS
Logan Intl.
$147 Roundtrip, found 2 hours ago
$147
Roundtrip
found 2 hours ago
Select Delta flight, departing Wed, Aug 12 from Ronald Reagan Washington National to Logan Intl., returning Wed, Aug 19, priced at $147 found 2 hours ago
Tue, Jun 30 - Wed, Jul 8
DCA
Ronald Reagan Washington National
BOS
Logan Intl.
$151 Roundtrip, found 6 hours ago
$151
Roundtrip
found 6 hours ago
Select Delta flight, departing Tue, Jun 30 from Ronald Reagan Washington National to Logan Intl., returning Wed, Jul 8, priced at $151 found 6 hours ago
Wed, Aug 12 - Wed, Aug 19
DCA
Ronald Reagan Washington National
BOS
Logan Intl.
$157 Roundtrip, found 2 hours ago
$157
Roundtrip
found 2 hours ago
Select United flight, departing Wed, Aug 12 from Ronald Reagan Washington National to Logan Intl., returning Wed, Aug 19, priced at $157 found 2 hours ago
Thu, May 28 - Tue, Jun 2
DCA
Ronald Reagan Washington National
BOS
Logan Intl.
$157 Roundtrip, found 2 hours ago
$157
Roundtrip
found 2 hours ago
Select JetBlue Airways flight, departing Thu, May 28 from Ronald Reagan Washington National to Logan Intl., returning Tue, Jun 2, priced at $157 found 2 hours ago
Tue, Jun 30 - Wed, Jul 8
DCA
Ronald Reagan Washington National
BOS
Logan Intl.
$160 Roundtrip, found 6 hours ago
$160
Roundtrip
found 6 hours ago
Select United flight, departing Tue, Jun 30 from Ronald Reagan Washington National to Logan Intl., returning Wed, Jul 8, priced at $160 found 6 hours ago
Thu, May 28 - Tue, Jun 2
DCA
Ronald Reagan Washington National
BOS
Logan Intl.
$174 Roundtrip, found 2 hours ago
$174
Roundtrip
found 2 hours ago
Select Delta flight, departing Thu, May 28 from Ronald Reagan Washington National to Logan Intl., returning Tue, Jun 2, priced at $174 found 2 hours ago
Thu, May 28 - Tue, Jun 2
DCA
Ronald Reagan Washington National
BOS
Logan Intl.
$177 Roundtrip, found 2 hours ago
$177
Roundtrip
found 2 hours ago
Select United flight, departing Thu, May 28 from Ronald Reagan Washington National to Logan Intl., returning Tue, Jun 2, priced at $177 found 2 hours ago

Winthrop Flight Information

Traveling To
Winthrop
Destination Airport IATA Code
BOS
Number of Airlines Serving
Airlines
JetBlue Airways, American Airlines, United, Frontier Airlines, Delta
Flight Price
$135
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.
The Langham, Boston
5.0-star property

The Langham, Boston

Jul 3 - Jul 6

3 night stay

Atlanta (ATL) to Boston (BOS)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,520, price is now $989 per person
$989
per person
found 1 day ago
Furnished Apartment Near Longwood
3.0-star property

Furnished Apartment Near Longwood

Jun 16 - Jun 23

7 night stay

Chicago (ORD) to Boston (BOS)

Delta • Roundtrip • Coach
Save 100% on your flight
Price was $2,790, price is now $1,777 per person
$1,777
per person
found 1 day ago
The Boston Hotel
2.0-star property

The Boston Hotel

Jun 16 - Jun 23

7 night stay

Chicago (ORD) to Boston (BOS)

Delta • Roundtrip • Coach
Save 100% on your flight
Price was $2,595, price is now $1,701 per person
$1,701
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 Atlas Hotel
4.5-star property

The Atlas Hotel

9.6/10 Exceptional! (66 reviews)

Jun 25 - Jun 28

3 night stay

Atlanta (ATL) to Boston (BOS)

Frontier Airlines • Roundtrip • PremiumEconomy
Price was $1,358, price is now $1,056 per person
$1,056
per person
found 1 day ago
The Langham, Boston
5.0-star property

The Langham, Boston

9.6/10 Exceptional! (1,007 reviews)

Jun 25 - Jun 28

3 night stay

Atlanta (ATL) to Boston (BOS)

Frontier Airlines • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $2,493, price is now $1,703 per person
$1,703
per person
found 1 day ago
No complaints , everything . I would go back again and again.

Reviewed on Jan 12, 2026

The Ritz-Carlton, Boston
5.0-star property

The Ritz-Carlton, Boston

9/10 Wonderful! (453 reviews)

Jun 25 - Jun 28

3 night stay

Atlanta (ATL) to Boston (BOS)

Frontier Airlines • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $3,213, price is now $2,451 per person
$2,451
per person
found 1 day ago
Staff was amazing, eent above and beyond! Excellent service

Reviewed on Mar 5, 2026

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Winthrop first class flight packages

Price found within the past 48 hours. Click for updated prices.
Eurostars The Boxer
4.0-star property

Eurostars The Boxer

8.8/10 Excellent! (1,462 reviews)

Jul 3 - Jul 5

2 night stay

Tampa (TPA) to Boston (BOS)

American Airlines • Roundtrip • FirstClass
Price was $1,542, price is now $1,316 per person
$1,316
per person
found 1 day ago
well appointed room. thoughtful amenities. tv with netflix, toiletries, bathrobe, slippers and even an umbrella

Reviewed on Apr 14, 2026

Encore Boston Harbor
5.0-star property

Encore Boston Harbor

9.6/10 Exceptional! (3,741 reviews)

Jul 3 - Jul 5

2 night stay

Tampa (TPA) to Boston (BOS)

American Airlines • Roundtrip • FirstClass
Price was $1,562, price is now $1,391 per person
$1,391
per person
found 1 day ago
Beautiful views, helpful staff, gorgeous room, and perfect location.

Reviewed on Apr 22, 2026

The Whitney Hotel
4.0-star property

The Whitney Hotel

9.6/10 Exceptional! (548 reviews)

Jul 3 - Jul 5

2 night stay

Tampa (TPA) to Boston (BOS)

American Airlines • Roundtrip • FirstClass
Price was $1,645, price is now $1,484 per person
$1,484
per person
found 1 day ago
What a gem in Boston! I've been to Boston many times and usually stay closer to the Downtown Crossing area. This time we stayed at the Whitney, choosing to try out that part of town. We loved it! Bigger than a boutique hotel, but small enough to feel intimate. Charles St is a great walking street, and we loved the location. The room was on the ground level (actually partly below ground) but was excellent! Well-appointed room, a good amount of space for Boston, and super professional staff. I'll be back when I come back to Boston

Reviewed on Jul 30, 2024

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Winthrop

Finding cheap flights to Winthrop is easy when you have Orbitz at your fingertips. Not only does Orbitz offer great deals on Winthrop flights, but we also include some special extras to make booking a breeze. Just check out our:

Mobile Site and Apps

With Orbitz’s mobile site, m.orbitz.com, you can book your flights to Winthrop through your smartphone or tablet’s Web browser. Plus, our free downloadable apps for Android and iPhone mean it’s just a simple click to access your flight updates and alerts. You can even book exclusive mobile-only deals on hotels to go with your flights to Winthrop—even on the same day.

Pick and Choose or Book Full Vacation Packages

Don’t just be satisfied with great deals on Winthrop flights—go for the full package! With Orbitz, you can also find fantastic savings on the perfect hotel, car rental, cruise, and even activities, so you don’t waste your trip waiting in line but have the time to enjoy your trip. Pick and choose the add-ons you need, or book an entire vacation package for greater overall discounts.

Rewards That Are Miles Better

Booking directly with an airline earns you air miles or points, and you can get those same rewards with booking on Orbitz too. When you book qualifying flights to Winthrop with Orbitz, just add in your frequent flyer number during your online booking and your details will be sent to your program.

Great Deals Every Day

Add in our extra savings on packages, free nights, and other discounts, and you know you are in good hands.

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 $135 and $177. If you were flying one-way out of Washington (DCA), you could have snapped up fares from as low as $72.
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.