Cheap flights To Winthrop (BOS) from $39

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Cheap Flights to Winthrop from $39 One Way, $78 Round Trip

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

Wed, May 20 - Wed, May 27
RDU
Raleigh - Durham Intl.
BOS
Logan Intl.
$78 Roundtrip, found 2 days ago
$78
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, May 20 from Raleigh - Durham Intl. to Logan Intl., returning Wed, May 27, priced at $78 found 2 days ago
Sat, May 23 - Mon, Jun 1
RDU
Raleigh - Durham Intl.
BOS
Logan Intl.
$98 Roundtrip, found 3 days ago
$98
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, May 23 from Raleigh - Durham Intl. to Logan Intl., returning Mon, Jun 1, priced at $98 found 3 days ago
Sun, May 3 - Sat, May 9
RDU
Raleigh - Durham Intl.
BOS
Logan Intl.
$100 Roundtrip, found 2 days ago
$100
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sun, May 3 from Raleigh - Durham Intl. to Logan Intl., returning Sat, May 9, priced at $100 found 2 days ago
Thu, Apr 9 - Sun, Apr 12
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$105 Roundtrip, found 5 days ago
$105
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Apr 9 from Raleigh - Durham Intl. to Portsmouth Intl., returning Sun, Apr 12, priced at $105 found 5 days ago
Mon, May 4 - Wed, May 13
RDU
Raleigh - Durham Intl.
BOS
Logan Intl.
$106 Roundtrip, found 6 days ago
$106
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Mon, May 4 from Raleigh - Durham Intl. to Logan Intl., returning Wed, May 13, priced at $106 found 6 days ago
Thu, Apr 9 - Sun, Apr 12
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$109 Roundtrip, found 5 days ago
$109
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Apr 9 from Raleigh - Durham Intl. to Portsmouth Intl., returning Sun, Apr 12, priced at $109 found 5 days ago
Thu, Apr 9 - Sun, Apr 12
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$109 Roundtrip, found 6 days ago
$109
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, Apr 9 from Raleigh - Durham Intl. to Portsmouth Intl., returning Sun, Apr 12, priced at $109 found 6 days ago
Fri, May 8 - Sat, May 9
RDU
Raleigh - Durham Intl.
BOS
Logan Intl.
$111 Roundtrip, found 1 day ago
$111
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, May 8 from Raleigh - Durham Intl. to Logan Intl., returning Sat, May 9, priced at $111 found 1 day ago
Thu, Apr 9 - Sun, Apr 12
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$114 Roundtrip, found 6 days ago
$114
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, Apr 9 from Raleigh - Durham Intl. to Portsmouth Intl., returning Sun, Apr 12, priced at $114 found 6 days ago
Sat, May 30 - Sat, Jun 6
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$117 Roundtrip, found 5 days ago
$117
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Sat, May 30 from Orlando Intl. to Portsmouth Intl., returning Sat, Jun 6, priced at $117 found 5 days ago

Winthrop Flight Information

Traveling To
Winthrop
Destination Airport IATA Code
BOS
Number of Airlines Serving
Airlines
Frontier Airlines, Breeze Airways
Flight Price
$78
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 Boxboro Regency
3.0-star property

The Boxboro Regency

May 15 - May 19

4 night stay

Chicago (ORD) to Boston (BOS)

United • Roundtrip • Coach
Price was $530, price is now $408 per person
$408
per person
found 1 day ago
Boston Harbor Hotel
5.0-star property

Boston Harbor Hotel

Apr 24 - Apr 26

2 night stay

Chicago (CHI) to Boston (BOS)

JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $1,207, price is now $773 per person
$773
per person
found 1 day ago
The Inn at Hastings Park, Relais & Chateaux - Boston
4.0-star property

The Inn at Hastings Park, Relais & Chateaux - Boston

May 15 - May 19

4 night stay

Chicago (ORD) to Boston (BOS)

United • Roundtrip • Coach
Save 100% on your flight
Price was $1,515, price is now $1,127 per person
$1,127
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 Hotel Salem
3.0-star property

The Hotel Salem

9.2/10 Wonderful! (1,000 reviews)

May 4 - May 7

3 night stay

Minneapolis (MSP) to Boston (BOS)

Delta • Roundtrip • PremiumEconomy
Price was $1,416, price is now $968 per person
$968
per person
found 1 day ago
Clean and new property staff is excellent will come again

Reviewed on Aug 24, 2025

The Revolution Hotel
3.5-star property

The Revolution Hotel

9/10 Wonderful! (2,535 reviews)

May 4 - May 7

3 night stay

Minneapolis (MSP) to Boston (BOS)

Delta • Roundtrip • PremiumEconomy
Price was $1,559, price is now $1,019 per person
$1,019
per person
found 1 day ago
Super clean bathrooms awesome staff

Reviewed on Jan 19, 2026

The Wylie Inn and Conference Center at Endicott College
3.5-star property

The Wylie Inn and Conference Center at Endicott College

9.2/10 Wonderful! (1,174 reviews)

May 4 - May 7

3 night stay

Minneapolis (MSP) to Boston (BOS)

Delta • Roundtrip • PremiumEconomy
Price was $1,509, price is now $1,006 per person
$1,006
per person
found 1 day ago
Great front desk service. Like the newly opened bar and mini restaurant. Will stay here again!

Reviewed on Nov 16, 2025

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Winthrop first class flight packages

Price found within the past 48 hours. Click for updated prices.
Omni Parker House
4.5-star property

Omni Parker House

9/10 Wonderful! (3,322 reviews)

Apr 28 - Apr 30

2 night stay

Chicago (ORD) to Boston (BOS)

American Airlines • Roundtrip • FirstClass
Price was $854, price is now $708 per person
$708
per person
found 1 day ago
The room was very small and the bathroom was smaller. It was fine because it was just one night and in the winter, so we got a great rate. We just kept saying thank goodness we didn't pay the high season rate. Location is amazing!

Reviewed on Mar 4, 2026

Boston Harbor Hotel
5.0-star property

Boston Harbor Hotel

9.8/10 Exceptional! (1,001 reviews)

Apr 28 - Apr 30

2 night stay

Chicago (ORD) to Boston (BOS)

American Airlines • Roundtrip • FirstClass
Save 100% on your flight
Price was $2,111, price is now $1,365 per person
$1,365
per person
found 1 day 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

Club Quarters Hotel Faneuil Hall, Boston
4.0-star property

Club Quarters Hotel Faneuil Hall, Boston

9/10 Wonderful! (2,995 reviews)

Apr 28 - Apr 30

2 night stay

Chicago (ORD) to Boston (BOS)

American Airlines • Roundtrip • FirstClass
Price was $904, price is now $769 per person
$769
per person
found 1 day ago
Staff was great and this is a great location for seeing all the things you want to see in Boston. Issues: Room was hot, elevator was under repair and no fridges in room

Reviewed on Nov 11, 2025

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Winthrop

Save more on flights to Winthrop while making top-quality travel arrangements. At Orbitz we provide access to low cost flights, hotel lodgings and other discounts, along with superior customer service and an unbeatable satisfaction guarantee.

Compare And Book Discount Flights to Winthrop

Now it is easier than ever to find a discount Winthrop flight. Orbitz users can compare airfares for both international and domestic flights and can quickly determine the best hotels and car rental companies to use. You may also check out hotel and other reviews along with a number of travel tips, making your visit to an unfamiliar destination enjoyable and hassle-free.

Use Your Mobile Phone To Secure A Low Cost Flight To Winthrop

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Boost Your Frequent Flyer Rewards

You even retain your ability to earn frequent flier points and rewards when purchasing your tickets with Orbitz for Winthrop flights. Enter your frequent flyer information into your Orbitz profile to start earning rewards.

You will find that Orbitz is a very low cost, yet very effective travel planner. Free updates via your mobile phone device will help to keep you and all relevant parties informed of important flight updates. With access to unbeatable sales on all travel essentials, Orbitz makes booking an affordable flight to Winthrop a breeze.

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 $78 and $117. If you were flying one-way out of Raleigh (RDU), you could have snapped up fares from as low as $39.
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.