Cheap flights To Winthrop (BOS) from $44

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Cheap Flights to Winthrop from $44 One Way, $87 Round Trip

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

Wed, Sep 3 - Tue, Sep 9
MCO
Orlando Intl.
BOS
Logan Intl.
$87 Roundtrip, found 2 hours ago
$87
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Wed, Sep 3 from Orlando Intl. to Logan Intl., returning Tue, Sep 9, priced at $87 found 2 hours ago
Tue, Sep 2 - Sat, Sep 6
MCO
Orlando Intl.
BOS
Logan Intl.
$92 Roundtrip, found 3 hours ago
$92
Roundtrip
found 3 hours ago
Select Spirit Airlines flight, departing Tue, Sep 2 from Orlando Intl. to Logan Intl., returning Sat, Sep 6, priced at $92 found 3 hours ago
Sat, Dec 6 - Sat, Dec 13
RSW
Southwest Florida Intl.
PSM
Portsmouth Intl.
$102 Roundtrip, found 15 hours ago
$102
Roundtrip
found 15 hours ago
Select Breeze Airways flight, departing Sat, Dec 6 from Southwest Florida Intl. to Portsmouth Intl., returning Sat, Dec 13, priced at $102 found 15 hours ago
Sat, Oct 4 - Wed, Oct 8
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$102 Roundtrip, found 1 hour ago
$102
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Sat, Oct 4 from Orlando Intl. to Portsmouth Intl., returning Wed, Oct 8, priced at $102 found 1 hour ago
Sat, Sep 20 - Wed, Sep 24
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$103 Roundtrip, found 1 hour ago
$103
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Sat, Sep 20 from Orlando Intl. to Portsmouth Intl., returning Wed, Sep 24, priced at $103 found 1 hour ago
Wed, Oct 22 - Wed, Oct 29
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$107 Roundtrip, found 1 hour ago
$107
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Wed, Oct 22 from Orlando Intl. to Portsmouth Intl., returning Wed, Oct 29, priced at $107 found 1 hour ago
Sat, Aug 16 - Tue, Sep 2
MCO
Orlando Intl.
BOS
Logan Intl.
$107 Roundtrip, found 1 day ago
$107
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sat, Aug 16 from Orlando Intl. to Logan Intl., returning Tue, Sep 2, priced at $107 found 1 day ago
Thu, Aug 28 - Wed, Sep 3
MCO
Orlando Intl.
BOS
Logan Intl.
$109 Roundtrip, just found
$109
Roundtrip
just found
Select Spirit Airlines flight, departing Thu, Aug 28 from Orlando Intl. to Logan Intl., returning Wed, Sep 3, priced at $109 just found
Sat, Sep 6 - Sun, Sep 7
MCO
Orlando Intl.
BOS
Logan Intl.
$109 Roundtrip, just found
$109
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, Sep 6 from Orlando Intl. to Logan Intl., returning Sun, Sep 7, priced at $109 just found
Wed, Oct 22 - Wed, Oct 29
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$112 Roundtrip, found 1 hour ago
$112
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Wed, Oct 22 from Orlando Intl. to Portsmouth Intl., returning Wed, Oct 29, priced at $112 found 1 hour ago

Winthrop Flight Information

Traveling To
Winthrop
Destination Airport IATA Code
BOS
Number of Airlines Serving
Airlines
Spirit Airlines, Breeze Airways
Flight Price
$87
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.
Hotel 1620 Plymouth Harbor
3.0-star property

Hotel 1620 Plymouth Harbor

Sep 26 - Sep 29

3 night stay

Houston (IAH) to Boston (BOS)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
The Langham, Boston
5.0-star property

The Langham, Boston

Sep 6 - Sep 9

3 night stay

Dallas (DFW) to Boston (BOS)

Spirit Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
per person
found 2 days ago
Raffles Boston
5.0-star property

Raffles Boston

Sep 19 - Sep 22

3 night stay

Dallas (DFW) to Boston (BOS)

Spirit Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
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See all available trips from Houston to Winthrop
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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

8.6/10 Excellent! (2,098 reviews)

Sep 3 - Sep 10

7 night stay

Chicago (ORD) to Boston (BOS)

American Airlines • Roundtrip • FirstClass
Save 100% on your flight
per person
found 1 day ago
The room was clean, had everything we needed and the location was amazing. Excellent food options and so much to walk around and see.

Reviewed on Jul 13, 2025

Raffles Boston
5.0-star property

Raffles Boston

9.6/10 Exceptional! (132 reviews)

Sep 3 - Sep 10

7 night stay

Chicago (ORD) to Boston (BOS)

American Airlines • Roundtrip • FirstClass
Save 100% on your flight
per person
found 1 day ago
Excellent services.

Reviewed on Dec 29, 2024

The Dagny Boston
4.0-star property

The Dagny Boston

9.4/10 Exceptional! (6,056 reviews)

Sep 3 - Sep 10

7 night stay

Chicago (ORD) to Boston (BOS)

American Airlines • Roundtrip • FirstClass
Save 100% on your flight
per person
found 1 day ago
This was our first time to Boston. We fell in love with Boston and this hotel. The location is absolutely PERFECT! We will definitely book again here!

Reviewed on Jul 29, 2025

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See all available trips from Chicago to Winthrop
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Winthrop

Get the absolute lowest prices on flights to Winthrop by shopping with Orbitz. Orbitz is the most efficient travel planner around, allowing you to search, compare and book discount domestic and international flights fast. With cutting-edge mobile tools and access to frequent flier rewards programs, we have everything you need for both your routine and holiday excursions.

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New mobile app tools enable those with hand-held devices to scout out the best bargains and to secure tickets from any location. If you have an iPhone, iPad or Android device, you may take advantage of special discounts, only available to mobile device customers, when you book hotel rooms or car rentals on the same day as booking Winthrop flights.

Avoid Check-In Hassles When Traveling On Flights to Winthrop

Orbitz also provides an array of resources that can help you eliminate most check-in hassles. Detailed baggage information is continually available for Winthrop flights. Mobile apps can also be used to share travel itineraries with family members or business associates.

Keeping Everyone Up To Date

When you download the free Orbitz mobile phone app, you can get regular and free flight updates. These will keep you informed of important scheduling changes. Updates can even be sent to several contacts, helping to keep everyone current on anticipated arrival times and all other relevant flight details.

Orbitz makes traveling on a budget very easy to do. We provide everything you need to plan your ideal trip from start to finish. Getting there and back again is a snap when you book your Winthrop flight using 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 $87 and $112. If you were flying one-way out of Orlando (MCO), you could have snapped up fares from as low as $44.
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.

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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.