Cheap flights To Isles of Shoals (BOS) from $53

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Cheap Flights to Isles of Shoals from $53 One Way, $102 Round Trip

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

Thu, Sep 3 - Sun, Sep 6
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$102 Roundtrip, found 15 hours ago
$102
Roundtrip
found 15 hours ago
Select Breeze Airways flight, departing Thu, Sep 3 from Raleigh - Durham Intl. to Portsmouth Intl., returning Sun, Sep 6, priced at $102 found 15 hours ago
Thu, Sep 3 - Sun, Sep 6
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$107 Roundtrip, found 15 hours ago
$107
Roundtrip
found 15 hours ago
Select Breeze Airways flight, departing Thu, Sep 3 from Raleigh - Durham Intl. to Portsmouth Intl., returning Sun, Sep 6, priced at $107 found 15 hours ago
Thu, Sep 3 - Sun, Sep 6
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$112 Roundtrip, found 15 hours ago
$112
Roundtrip
found 15 hours ago
Select Breeze Airways flight, departing Thu, Sep 3 from Raleigh - Durham Intl. to Portsmouth Intl., returning Sun, Sep 6, priced at $112 found 15 hours ago
Thu, Sep 24 - Sun, Sep 27
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$117 Roundtrip, found 9 hours ago
$117
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Thu, Sep 24 from Raleigh - Durham Intl. to Portsmouth Intl., returning Sun, Sep 27, priced at $117 found 9 hours ago
Thu, Sep 24 - Sun, Sep 27
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$122 Roundtrip, found 9 hours ago
$122
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Thu, Sep 24 from Raleigh - Durham Intl. to Portsmouth Intl., returning Sun, Sep 27, priced at $122 found 9 hours ago
Sat, May 30 - Thu, Jun 4
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$129 Roundtrip, found 2 days ago
$129
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sat, May 30 from Orlando Intl. to Portsmouth Intl., returning Thu, Jun 4, priced at $129 found 2 days ago
Thu, May 7 - Sun, May 10
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$131 Roundtrip, found 4 days ago
$131
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, May 7 from Raleigh - Durham Intl. to Portsmouth Intl., returning Sun, May 10, priced at $131 found 4 days ago
Thu, May 28 - Sun, May 31
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$133 Roundtrip, found 4 days ago
$133
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, May 28 from Orlando Intl. to Portsmouth Intl., returning Sun, May 31, priced at $133 found 4 days ago
Thu, Sep 3 - Sun, Sep 6
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$134 Roundtrip, found 1 day ago
$134
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Sep 3 from Orlando Intl. to Portsmouth Intl., returning Sun, Sep 6, priced at $134 found 1 day ago
Thu, May 28 - Sun, May 31
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$135 Roundtrip, found 4 days ago
$135
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, May 28 from Orlando Intl. to Portsmouth Intl., returning Sun, May 31, priced at $135 found 4 days ago

Isles of Shoals Flight Information

Traveling To
Isles of Shoals
Destination Airport IATA Code
BOS
Number of Airlines Serving
Airlines
Breeze Airways
Flight Price
$102
Earliest Departing Flight
Latest Departing Flight

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Isles of Shoals economy flight packages

Price found within the past 48 hours. Click for updated prices.
By the Sea Guests Bed & Breakfast & Suites
3.5-star property

By the Sea Guests Bed & Breakfast & Suites

Jun 19 - Jun 22

3 night stay

Chicago (CHI) to Boston (BOS)

United • Roundtrip • Coach
Save 100% on your flight
Price was $920, price is now $580 per person
$580
per person
found 1 day ago
Crowne Plaza Boston - Woburn by IHG
3.5-star property

Crowne Plaza Boston - Woburn by IHG

Jun 16 - Jun 24

8 night stay

Chicago (CHI) to Boston (BOS)

American Airlines • Coach

Boston (BOS) to Chicago (CHI)

Southwest Airlines • Coach
Save 100% on your flight
Price was $1,206, price is now $785 per person
$785
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 4 hours ago
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Isles of Shoals premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel Ivy Boston Common
2.5-star property

Hotel Ivy Boston Common

8.4/10 Very Good! (1,430 reviews)

Jun 16 - Jun 18

2 night stay

Seattle (SEA) to Boston (BOS)

JetBlue Airways • Roundtrip • PremiumEconomy
Price was $1,513, price is now $1,272 per person
$1,272
per person
found 7 hours ago
Very convenient place to stay

Reviewed on Aug 18, 2025

Luxury Apartments by Hyatus at Boston Everett
5.0-star property

Luxury Apartments by Hyatus at Boston Everett

10/10 Exceptional! (1 review)

Jun 16 - Jun 18

2 night stay

Seattle (SEA) to Boston (BOS)

JetBlue Airways • Roundtrip • PremiumEconomy
Price was $2,544, price is now $2,097 per person
$2,097
per person
found 6 hours ago
XV Beacon
5.0-star property

XV Beacon

9.4/10 Exceptional! (388 reviews)

Jun 16 - Jun 18

2 night stay

Seattle (SEA) to Boston (BOS)

JetBlue Airways • Roundtrip • PremiumEconomy
Price was $2,440, price is now $2,065 per person
$2,065
per person
found 7 hours ago
Love this place! Can’t wait to come back!

Reviewed on Jun 30, 2024

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Isles of Shoals first class flight packages

Price found within the past 48 hours. Click for updated prices.
Quality Inn & Suites South Portland
2.5-star property

Quality Inn & Suites South Portland

6.6/10 (1,004 reviews)

Jun 28 - Jul 5

7 night stay

Chicago (CHI) to Boston (BOS)

American Airlines • Roundtrip • FirstClass
Price was $1,534, price is now $1,341 per person
$1,341
per person
found 1 day ago
Room was clean and comfortable

Reviewed on Oct 20, 2025

HomeAwhile
4.0-star property

HomeAwhile

9.6/10 Exceptional! (27 reviews)

Jun 28 - Jul 5

7 night stay

Chicago (CHI) to Boston (BOS)

American Airlines • Roundtrip • FirstClass
Price was $1,897, price is now $1,572 per person
$1,572
per person
found 1 day ago
Great location for our weekend trip to Portland. Emily went out of her way to accommodate a request for me! Beyond clean rooms with a lot more space in standard rooms than most hotels. I understand the concept of this hotel but I was shocked to see you had to pay for hand soap and that an iron or hair dryer wasn’t in the room. Other than that, this place did not disappoint a still a great value for the price! My wife and I would stay here again next time we visit the Portland area!

Reviewed on Apr 19, 2026

The McKernan Inn
3.0-star property

The McKernan Inn

9.2/10 Wonderful! (98 reviews)

Jun 28 - Jul 5

7 night stay

Chicago (CHI) to Boston (BOS)

American Airlines • Roundtrip • FirstClass
Price was $2,697, price is now $2,308 per person
$2,308
per person
found 1 day ago
Location is great. We really enjoyed walking on the beach. Our room wasn’t bad but not great either. Def needs to be refreshed. The blinds in several windows were removed and the curtains didn’t block the light so we were up early. Furniture is in rough shape. Prolly wouldn’t stay here again but it was fine for one night

Reviewed on Nov 3, 2025

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Isles of Shoals

Snag some “suite” deals when you add cheap hotel rooms to Isles of Shoals 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.

Budget Prices, Luxury Life

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Fun for All

While shopping Orbitz sales on Isles of Shoals flights, remember to throw in some fun. Ticket sales for music, theatre, sports and more can be found on the Activities page. Just tell us what you want to do, and Orbitz will save your seat.

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 Isles of Shoals 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 Isles of Shoals. 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

How much is a flight to Isles of Shoals?
Travelers from far and wide nabbed round-trip flight deals ranging from $102 to $135 this week to Isles of Shoals. Kicking off your journey from Raleigh (RDU)? The best one-way prices started at just $53.
How to book the cheapest flight to Isles of Shoals?
Using Orbitz, you'll find some of the best flight deals around from a terrific range of airlines. But if you're eager to increase your likelihood of snapping up cheap flights to Isles of Shoals, here are some suggestions to keep in mind:

  • Consider taking off from or landing at alternative airports for a cheaper fare. Enter your preferred departure and arrival airports in the form fields, then select the 'Nearby airports' function below. It will list any available options.
  • If your travel plans aren't etched in stone, click on the 'Show flexible dates' link to see the flight deals across different departure dates. If you find a better fare, book it.
  • You can also use the 'Show options' function to filter results for your preferred airline, seating class, nonstop flights and refundable flights. Under 'Sort & Filter' to the left, you can even choose the time of day you want to fly.
  • The early bird catches the most rewarding deals, so book as soon as you've worked out your travel dates. The cheapest airfares sell out first and prices climb as the departure date nears.
  • Bundle your flights, hotels and car rentals into a package deal and enjoy discounts. Save your hard-earned money for things that really excite you, like discovering every corner of Isles of Shoals.
  • If it's an option, avoid flying in high seasons. Airfares are usually at their most expensive during school breaks, summer and around other vacation times like Easter, Thanksgiving and Christmas.

What is the best time to book a flight to Isles of Shoals?
Book in January, February or August for the lowest airfares to Isles of Shoals. Once you've located a bargain, lock it in — cheap flights are known to pop up and then vanish in the click of a button.
What day of the week is the cheapest to book a flight to Isles of Shoals?
Typically, Tuesdays, Wednesdays and Saturdays are the cheapest days of the week to book flights to Isles of Shoals. If you want unbeatable airfares, search across those days and you could land an excellent flight deal.
What is the cheapest day of the week to fly to Isles of Shoals?
Think about flying early in the week if you want to score cheap flights to Isles of Shoals. Orbitz data from 2020 shows Monday is typically the most affordable day to fly out, followed by Tuesday. Saturdays were shown to have the highest ticket fares. Presumably, this is because many travelers prefer to start their escape when the weekend rolls around.
What is the cheapest month to fly to Isles of Shoals?
Get set to jet for less in August. This is generally the best month to get on a plane if you want cheap flights to Isles of Shoals, based on Orbitz data. The costliest time to take off is June, so avoid this month if you can.
Which airlines allow free cancellation?
When searching for flights on Orbitz, select "Filter by flexible change policies." This filter will show you all the carriers offering free cancellation and no change fees. Breathe easy knowing that if things change, your flight can too.
What do I need for the flight to Isles of Shoals?
Whether you're a frequent flyer or it's your first time in the air, it helps to be organized on your journey. Here are some key things to take into consideration:

  • Travel documents such as e-tickets and some identification will be required. To avoid any unnecessary delays when you check in, make sure your booking is under the exact name, birth date and gender as your current ID.
  • A well-packed carry-on bag is important for any medium-haul flight. With at least a few hours to kill, you'll need something to keep you amused on your trip. We recommend a good book (or trashy magazine), and something to munch on.
  • No matter what the season is, airplane cabins can often get a little chilly. Take a sweater on the flight with you to stay nice and warm.

How do I get cheap first-class/business deals to Isles of Shoals?
Savvy travelers are pros at finding first or business-class airfares to Isles of Shoals without the hefty price tag. You can do the same with these practical tips:

  • Being flexible isn't confined to yoga. Avoid locking in your travel dates so you can pick up more affordable airfares when a huge sale drops.
  • Search for a budget airline that offers seats in business class. They often come with more space and a glass of Champagne — and a nicer price.
  • Make a bid for an upgrade. Some airlines hold online auctions that let you offer a price for a seat up the front. You may also be able to upgrade with points earned through a flight rewards program.

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.