Cheap flights To Winthrop (BOS) from $53

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Cheap Flights to Winthrop from $53 One Way, $113 Round Trip

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

Sat, Sep 12 - Sat, Sep 12
MCO
Orlando Intl.
BOS
Logan Intl.
$113 Roundtrip, found 16 hours ago
$113
Roundtrip
found 16 hours ago
Select Frontier Airlines flight, departing Sat, Sep 12 from Orlando Intl. to Logan Intl., returning Sat, Sep 12, priced at $113 found 16 hours ago
Thu, Aug 27 - Mon, Aug 31
RDU
Raleigh - Durham Intl.
BOS
Logan Intl.
$114 Roundtrip, just found
$114
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, Aug 27 from Raleigh - Durham Intl. to Logan Intl., returning Mon, Aug 31, priced at $114 just found
Wed, Jul 29 - Wed, Aug 5
RDU
Raleigh - Durham Intl.
BOS
Logan Intl.
$117 Roundtrip, just found
$117
Roundtrip
just found
Select Frontier Airlines flight, departing Wed, Jul 29 from Raleigh - Durham Intl. to Logan Intl., returning Wed, Aug 5, priced at $117 just found
Sat, Sep 12 - Fri, Sep 18
MCO
Orlando Intl.
BOS
Logan Intl.
$118 Roundtrip, found 5 hours ago
$118
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Sat, Sep 12 from Orlando Intl. to Logan Intl., returning Fri, Sep 18, priced at $118 found 5 hours ago
Thu, Dec 3 - Sun, Dec 6
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$122 Roundtrip, found 1 day ago
$122
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Dec 3 from Raleigh - Durham Intl. to Portsmouth Intl., returning Sun, Dec 6, priced at $122 found 1 day ago
Thu, Sep 3 - Sun, Sep 6
RDU
Raleigh - Durham Intl.
BOS
Logan Intl.
$124 Roundtrip, found 7 hours ago
$124
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Thu, Sep 3 from Raleigh - Durham Intl. to Logan Intl., returning Sun, Sep 6, priced at $124 found 7 hours ago
Thu, Dec 3 - Sun, Dec 6
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$127 Roundtrip, found 1 day ago
$127
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Dec 3 from Raleigh - Durham Intl. to Portsmouth Intl., returning Sun, Dec 6, priced at $127 found 1 day ago
Wed, Jul 29 - Wed, Aug 5
RDU
Raleigh - Durham Intl.
BOS
Logan Intl.
$127 Roundtrip, just found
$127
Roundtrip
just found
Select Frontier Airlines flight, departing Wed, Jul 29 from Raleigh - Durham Intl. to Logan Intl., returning Wed, Aug 5, priced at $127 just found
Fri, Aug 28 - Sun, Aug 30
RDU
Raleigh - Durham Intl.
BOS
Logan Intl.
$131 Roundtrip, found 1 hour ago
$131
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Fri, Aug 28 from Raleigh - Durham Intl. to Logan Intl., returning Sun, Aug 30, priced at $131 found 1 hour ago
Tue, Nov 24 - Sat, Nov 28
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$132 Roundtrip, found 1 day ago
$132
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Tue, Nov 24 from Orlando Intl. to Portsmouth Intl., returning Sat, Nov 28, priced at $132 found 1 day ago

Winthrop Flight Information

Traveling To
Winthrop
Destination Airport IATA Code
BOS
Number of Airlines Serving
Airlines
Breeze Airways, Frontier Airlines
Flight Price
$113
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.
The Charles Hotel
4.0-star property

The Charles Hotel

Jul 24 - Jul 28

4 night stay

Chicago (ORD) to Boston (BOS)

Delta • Roundtrip • Coach
Save 100% on your flight
Price was $1,265, price is now $881 per person
$881
per person
found 1 day ago
Boston Lodge and Suites
4.0-star property

Boston Lodge and Suites

Aug 12 - Aug 17

5 night stay

Tampa (TPA) to Boston (BOS)

JetBlue Airways • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,692, price is now $1,040 per person
$1,040
per person
found 7 hours ago
The Inn at Hastings Park, Relais & Chateaux - Boston
4.0-star property

The Inn at Hastings Park, Relais & Chateaux - Boston

Aug 12 - Aug 17

5 night stay

Tampa (TPA) to Boston (BOS)

JetBlue Airways • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,698, price is now $1,246 per person
$1,246
per person
found 7 hours ago
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Winthrop premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel AKA Back Bay
4.5-star property

Hotel AKA Back Bay

9.4/10 Exceptional! (1,288 reviews)

Aug 14 - Aug 17

3 night stay

Chicago (ORD) to Boston (BOS)

JetBlue Airways • Non-stop roundtrip • PremiumEconomy
Price was $888, price is now $710 per person
$710
per person
found 9 hours ago
Excellent location. Walkable from Amtrak station and north end and south end. Well maintained property.

Reviewed on Mar 28, 2026

Boston Harbor Hotel
5.0-star property

Boston Harbor Hotel

9.8/10 Exceptional! (1,003 reviews)

Aug 3 - Aug 7

4 night stay

Los Angeles (LAX) to Boston (BOS)

JetBlue Airways • PremiumEconomy

Boston (BOS) to Los Angeles (LAX)

Frontier Airlines • PremiumEconomy
Price was $2,725, price is now $1,857 per person
$1,857
per person
found 19 hours ago
The staff is VERY attentive to all your needs. It just makes everything easy and more comfortable: room service to concierge to valet parking etc. etc.

Reviewed on Mar 24, 2024

The Langham, Boston
5.0-star property

The Langham, Boston

9.8/10 Exceptional! (1,010 reviews)

Aug 14 - Aug 17

3 night stay

Chicago (ORD) to Boston (BOS)

JetBlue Airways • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,182, price is now $860 per person
$860
per person
found 9 hours ago
No complaints , everything . I would go back again and again.

Reviewed on Jan 12, 2026

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Winthrop first class flight packages

Price found within the past 48 hours. Click for updated prices.
YOTEL Boston
4.0-star property

YOTEL Boston

8.8/10 Excellent! (2,555 reviews)

Aug 3 - Aug 7

4 night stay

Los Angeles (LAX) to Boston (BOS)

American Airlines • FirstClass

Boston (BOS) to Los Angeles (LAX)

United • FirstClass
Price was $2,872, price is now $2,820 per person
$2,820
per person
found 19 hours ago
Excellent weekend at the Yotel! Will stay there again for sure!

Reviewed on Apr 21, 2026

Seaport Hotel Boston
4.0-star property

Seaport Hotel Boston

9.6/10 Exceptional! (4,461 reviews)

Aug 3 - Aug 7

4 night stay

Los Angeles (LAX) to Boston (BOS)

American Airlines • FirstClass

Boston (BOS) to Los Angeles (LAX)

United • FirstClass
Price was $3,174, price is now $2,971 per person
$2,971
per person
found 19 hours ago
I prepaid in full prior to my trip.When checking out I was charged an additional $25 for "Destination Fees" each day, total $75. I felt totally ripped off. When I asked, I was told that it was something they charge everyone. I will not return.

Reviewed on May 29, 2026

The Westin Copley Place, Boston, a Marriott Hotel
4.0-star property

The Westin Copley Place, Boston, a Marriott Hotel

9.2/10 Wonderful! (1,486 reviews)

Aug 3 - Aug 7

4 night stay

Los Angeles (LAX) to Boston (BOS)

American Airlines • FirstClass

Boston (BOS) to Los Angeles (LAX)

United • FirstClass
Price was $2,946, price is now $2,914 per person
$2,914
per person
found 19 hours ago
Good choice for business visitors.

Reviewed on Jul 7, 2025

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Winthrop

Snag some “suite” deals when you add cheap hotel rooms to Winthrop flights at Orbitz. You can score tickets to ballgames, concerts and other activities while planning your low fare flights. For non-stop air tickets or planned layovers, Orbitz is your discount travel resource.

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Non-Stop or Stop and Visit

Will you be flying round-trip or one-way? Going directly from Point A to Point B? Maybe you’d like to have dinner with family and friends along the way. Whether you need non-stop flights to {destination.name} or lowest cost layovers on Winthrop flights, you will always find the best air travel prices at Orbitz.

All in One

Now you can custom design the perfect travel package with Orbitz and save more when booking your flights to Winthrop. Do you have a favorite airline, hotel or car rental company? Every page at Orbitz gives you complete freedom to create your travel plans according to your unique wants and needs. Orbitz is designed to meet your discount travel planning needs completely and conveniently.

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 $113 and $132. If you were flying one-way out of Orlando (MCO), you could have snapped up fares from as low as $53.
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.