Cheap flights To North Shore (BOS) from $51

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Cheap Flights to North Shore from $51 One Way, $102 Round Trip

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

Sat, Dec 6 - Sat, Dec 13
RSW
Southwest Florida Intl.
PSM
Portsmouth Intl.
$102 Roundtrip, found 5 hours ago
$102
Roundtrip
found 5 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 5 hours ago
Sat, Oct 11 - Wed, Oct 15
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$102 Roundtrip, found 3 hours ago
$102
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Sat, Oct 11 from Orlando Intl. to Portsmouth Intl., returning Wed, Oct 15, priced at $102 found 3 hours ago
Sat, Oct 11 - Wed, Oct 15
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$102 Roundtrip, found 23 hours ago
$102
Roundtrip
found 23 hours ago
Select Breeze Airways flight, departing Sat, Oct 11 from Orlando Intl. to Manchester-Boston Regional, returning Wed, Oct 15, priced at $102 found 23 hours ago
Sat, Sep 13 - Sat, Sep 13
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$103 Roundtrip, found 3 hours ago
$103
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Sat, Sep 13 from Orlando Intl. to Portsmouth Intl., returning Sat, Sep 13, priced at $103 found 3 hours ago
Mon, Aug 4 - Sat, Aug 16
MCO
Orlando Intl.
BOS
Logan Intl.
$106 Roundtrip, found 6 days ago
$106
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Mon, Aug 4 from Orlando Intl. to Logan Intl., returning Sat, Aug 16, priced at $106 found 6 days ago
Sat, Aug 30 - Sat, Sep 6
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$107 Roundtrip, found 11 hours ago
$107
Roundtrip
found 11 hours ago
Select Breeze Airways flight, departing Sat, Aug 30 from Orlando Intl. to Portsmouth Intl., returning Sat, Sep 6, priced at $107 found 11 hours ago
Sat, Aug 2 - Sat, Aug 9
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$111 Roundtrip, found 5 days ago
$111
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Sat, Aug 2 from Orlando Intl. to Portsmouth Intl., returning Sat, Aug 9, priced at $111 found 5 days ago
Sat, Aug 2 - Sat, Aug 9
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$112 Roundtrip, found 5 days ago
$112
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Sat, Aug 2 from Orlando Intl. to Portsmouth Intl., returning Sat, Aug 9, priced at $112 found 5 days ago
Sat, Sep 6 - Sat, Sep 13
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$113 Roundtrip, found 9 hours ago
$113
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Sat, Sep 6 from Orlando Intl. to Portsmouth Intl., returning Sat, Sep 13, priced at $113 found 9 hours ago
Sat, Aug 2 - Sat, Aug 9
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$114 Roundtrip, found 3 days ago
$114
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Sat, Aug 2 from Orlando Intl. to Portsmouth Intl., returning Sat, Aug 9, priced at $114 found 3 days ago

North Shore BOS Flight Information

Traveling To
North Shore
Destination Airport IATA Code
BOS
Number of Airlines Serving
9
Airlines
Breeze Airways, Spirit Airlines
Flight Price
$102
Earliest Departing Flight
AA 4642 8:19AM EDT
Latest Departing Flight
AF 2710 Aug 7 7:10PM EDT

Book Your Flight & Hotel Together & Save

North Shore economy flight packages

Price found within the past 48 hours. Click for updated prices.
Even Hotels Manchester Airport by IHG
3.5-star property

Even Hotels Manchester Airport by IHG

Sep 19 - Sep 22

3 night stay

Los Angeles (LAX) to Boston (BOS)

Spirit Airlines • Non-stop roundtrip • Coach
per person
found 1 day ago
Raffles Boston
5.0-star property

Raffles Boston

Sep 19 - Sep 22

3 night stay

Dallas (DFW) to Boston (BOS)

American Airlines • Coach

Boston (BOS) to Dallas (DFW)

Spirit Airlines • Coach
Save 100% on your flight
per person
found 1 day ago
The Beverly
3.0-star property

The Beverly

Sep 25 - Sep 29

4 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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North Shore first class flight packages

Price found within the past 48 hours. Click for updated prices.
Maverick Suites at 28 Fenway
3.0-star property

Maverick Suites at 28 Fenway

8.8/10 Excellent! (233 reviews)

Sep 3 - Sep 10

7 night stay

Chicago (ORD) to Boston (BOS)

American Airlines • Roundtrip • FirstClass
per person
just found
Our room had no chair or table, a real drawback as we had evening zoom meetings. They had a coffee maker, but drinking in bed? Putting on shoes? There’s no front desk so nowhere to check luggage if you arrive before 4 pm. We did manage to check in early after back and forth with their remote manager and several door code resets.

Reviewed on Jun 12, 2025

Global Luxury Suites Downtown Boston
4.0-star property

Global Luxury Suites Downtown Boston

8/10 Very Good! (566 reviews)

Sep 3 - Sep 10

7 night stay

Chicago (ORD) to Boston (BOS)

American Airlines • Roundtrip • FirstClass
per person
just found
Love the space - it has a big livingroom with lots of light comming through the windows

Reviewed on Feb 4, 2022

Battery Wharf Hotel, Boston Waterfront
4.5-star property

Battery Wharf Hotel, Boston Waterfront

8.6/10 Excellent! (1,606 reviews)

Sep 3 - Sep 10

7 night stay

Chicago (ORD) to Boston (BOS)

American Airlines • Roundtrip • FirstClass
Save 100% on your flight
per person
just found
Wonderful place to stay!

Reviewed on Jul 28, 2025

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See all available trips from Chicago to North Shore
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North Shore

If you are looking for discount prices on flights to North Shore then look no further than Orbitz. With some of the best deals available, cutting-edge technology, and great customer service, Orbitz makes booking North Shore flights easy and affordable.

Booking Made Easy

With Orbitz’s Display Matrix, booking flights to North Shore is simple. Just one glance gives you all the pricing information you need, including your discounts and savings. View all your options before selecting and booking your perfect North Shore flights.

Manage Travel Plans on the Move

By using Orbitz’s free apps for iPhone and Android, and an easy-to-use mobile browser at m.orbitz.com, booking flights to North Shore has never been so convenient. Check for updates and alerts wherever you are, or manage your booking quickly. And we also offer mobile exclusive deals on hotels, so don’t delay—book right away.

The Complete Package

Orbitz makes it stress-free to book North Shore flights, and we can also help you figure out the rest of your trip just as easily. If you need great deals on hotels and car rentals following your flights to North Shore, just add the details to your booking and search for the cheapest deals out there. And why waste time lining up for admission to attractions and events? With Orbitz, you can book tickets in advance and waltz straight in.

Low Price Guarantee

Booking your North Shore flights with Orbitz guarantees low prices every day, all day—no matter when and where you book. You will always find the best deals available, coupled with extra great savings and discounts for all around great value.

Frequently asked questions

Which airlines fly to North Shore?
With 20 airlines ready to whisk you off to North Shore, finding an ideal flight will be easy. Lock in your ticket with one of these well-known international carriers that operate services to Logan Intl. Airport (BOS):

  • JetBlue - 175 flights to North Shore per month
  • Delta - 158 flights to North Shore per month
  • Air Canada - 151 flights to North Shore per month

What is the best airport to fly to in North Shore?
There's one primary entry point for this area — Logan Intl. Airport (BOS). Book your airfares for this popular gateway and see all that North Shore has to offer.
How much is a flight to North Shore?
Travelers from near and far landed return-flight deals ranging from $102 to $114 this week to North Shore. Starting your journey from Orlando (MCO)? The cheapest one-way tickets were just $51.
How to book the cheapest flight to North Shore?
With some of the most exciting flight deals around, you'll always jet for less with Orbitz. The following useful tips will help you score cheap flights to North Shore — and leave you with more money to play with:

  • Consider taking off from or landing at nearby airports to save money. Enter your preferred departure and arrival airports in the form fields, then choose the 'Nearby airports' function below. It will list any available options.
  • If your travel plans aren't written in stone, click on the 'Show flexible dates' link to compare flight deals for multiple departure dates. You may find a cheaper fare.
  • Select 'Show options' to narrow down your search results. You can choose 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.
  • Reserve your seat as soon as you've worked out your travel dates. While you can get lucky on occasion, airfares rarely get more affordable as your date of departure approaches.
  • Think about bundling your hotels, flights and car rentals into one convenient package deal to save cash.
  • Don't travel during the busy season if you can. By avoiding school vacations and summer, you can save a significant amount on your airfare.

How long is a flight to North Shore?
The time you spend in the air will depend on where you're jetting in from, whether that's the Northern states, the South or someplace else. Below are some of the most common routes to North Shore 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 North Shore?
Generally speaking, January is the best time to purchase your airfare. This is followed by February and August. Bear this in mind while searching for a cheap flight to North Shore.
What day of the week is the cheapest to book a flight to North Shore?
Make a booking on a Tuesday, Wednesday or Saturday. Generally, these are the cheapest days of the week to purchase fares to North Shore. The getaway of your dreams starts with a great flight deal!
What is the cheapest day of the week to fly to North Shore?
You can grab cheap flights to North Shore by hopping on a plane on a Monday, according to Orbitz data from 2020. Tuesday is also more affordable, while Saturday has the most expensive airfares. Whether you prefer to save a bundle or fly on whichever day is convenient, you'll always get a good deal with Orbitz.
What is the cheapest month to fly to North Shore?
Consider jetting off during August if you're on a budget. Orbitz data has found that it's generally the best month for cheap flights to North Shore. June is when airfares really go up.
Which airlines allow free cancellation?
Orbitz makes it a cinch to find airlines offering fare flexibility. Simply click on "Filter by flexible change policies" when searching for your North Shore flights and voila! You'll see options that include free cancellation within 24 hours of booking, no change fees and of course, the very best price.
What do I need for the flight to North Shore?
There is so much to plan for any big journey, so it's nice to get a little bit of help along the way. Here are a few tips to ensure you're organized for take off:

  • Travel paperwork such as visas and identification are a must. To avoid any unnecessary delays when checking in, make sure your booking is made with the exact name, gender and birth date as listed on your government-issued ID.
  • A well-packed carry-on bag is a must-have for any medium-haul journey. With a few hours or more up your sleeve, you'll want something to keep you busy on your trip. We recommend a good book or magazine, and something to munch on.
  • No matter what the season is, plane cabins (and airports) can often get quite cold. Bring an extra layer with you on your journey to stay cozy and warm.

How many direct flights are there to North Shore?
There are 1,287 direct flights to North Shore every month, which means you won't have to deal with any boring stopovers. Book a fare with JetBlue Airways or Delta Air Lines and then kick back, relax and enjoy the journey. American Airlines, Cape Air, United Airlines and Southwest Airlines also operate nonstop flights to North Shore.
How do I get cheap first-class/business deals to North Shore?
There are ways of booking first or business-class fares to North Shore that won't burn through your savings. Claim a seat in the pointy end of the plane for less with these handy tips:

  • Be flexible. By being open to other travel dates, you'll have better odds of finding a deal on your airfares.
  • Search for a budget airline that offers seats in business class. They usually come with extra space and a glass of bubbly — and a more affordable price.
  • 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 loyalty scheme.

What is the best time to go to North Shore?
North Shore is an exciting getaway destination year-round, but the most popular months to visit are May, July and August. If you're a fan of warmer weather, head there during the summer months. Like most places in the Northern Hemisphere, the summer season gets underway June 20. At this time, temperatures usually hover between 65 ºF and 75 ºF during the daytime.

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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.