Cheap flights To Shelter Island (LGA) from $41

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

Cheap Flights to Shelter Island from $41 One Way, $78 Round Trip

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

Fri, Jan 15 - Mon, Jan 18
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$78 Roundtrip, found 6 days ago
$78
Roundtrip
found 6 days ago
Select Avelo Airlines flight, departing Fri, Jan 15 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, Jan 18, priced at $78 found 6 days ago
Thu, Sep 3 - Sat, Sep 12
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$88 Roundtrip, just found
$88
Roundtrip
just found
Select Avelo Airlines flight, departing Thu, Sep 3 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Sat, Sep 12, priced at $88 just found
Thu, Aug 27 - Wed, Sep 2
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$91 Roundtrip, found 2 days ago
$91
Roundtrip
found 2 days ago
Select Avelo Airlines flight, departing Thu, Aug 27 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Wed, Sep 2, priced at $91 found 2 days ago
Mon, Aug 10 - Fri, Aug 21
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$93 Roundtrip, found 4 days ago
$93
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Mon, Aug 10 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Fri, Aug 21, priced at $93 found 4 days ago
Sat, Sep 12 - Sat, Sep 19
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$102 Roundtrip, found 22 hours ago
$102
Roundtrip
found 22 hours ago
Select Breeze Airways flight, departing Sat, Sep 12 from Raleigh - Durham Intl. to Stewart Intl., returning Sat, Sep 19, priced at $102 found 22 hours ago
Fri, Aug 28 - Tue, Sep 1
TPA
Tampa Intl.
HVN
Tweed - New Haven Regional
$114 Roundtrip, found 4 days ago
$114
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Fri, Aug 28 from Tampa Intl. to Tweed - New Haven Regional, returning Tue, Sep 1, priced at $114 found 4 days ago
Sat, Sep 12 - Wed, Sep 16
TPA
Tampa Intl.
SWF
Stewart Intl.
$132 Roundtrip, found 1 day ago
$132
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sat, Sep 12 from Tampa Intl. to Stewart Intl., returning Wed, Sep 16, priced at $132 found 1 day ago
Sat, Oct 3 - Tue, Oct 6
TPA
Tampa Intl.
LGA
LaGuardia
$157 Roundtrip, found 4 hours ago
$157
Roundtrip
found 4 hours ago
Select Delta flight, departing Sat, Oct 3 from Tampa Intl. to LaGuardia, returning Tue, Oct 6, priced at $157 found 4 hours ago
Tue, Sep 22 - Wed, Sep 30
TPA
Tampa Intl.
JFK
John F. Kennedy Intl.
$157 Roundtrip, found 1 day ago
$157
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Sep 22 from Tampa Intl. to John F. Kennedy Intl., returning Wed, Sep 30, priced at $157 found 1 day ago
Sat, Oct 3 - Tue, Oct 6
TPA
Tampa Intl.
LGA
LaGuardia
$157 Roundtrip, found 4 hours ago
$157
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Sat, Oct 3 from Tampa Intl. to LaGuardia, returning Tue, Oct 6, priced at $157 found 4 hours ago

Shelter Island Flight Information

Traveling To
Shelter Island
Destination Airport IATA Code
LGA
Number of Airlines Serving
Airlines
Avelo Airlines, Breeze Airways, United, Delta, American Airlines
Flight Price
$78
Earliest Departing Flight
Latest Departing Flight

Book Your Flight & Hotel Together & Save

Shelter Island economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel St. James
3.0-star property

Hotel St. James

Aug 22 - Aug 25

3 night stay

Dallas (DAL) to New York (JFK)

Southwest Airlines • Roundtrip • Coach
Price was $888, price is now $569 per person
$569
per person
found 1 day ago
Pestana Park Avenue
4.0-star property

Pestana Park Avenue

Aug 14 - Aug 21

7 night stay

Chicago (ORD) to New York (JFK)

JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $1,496, price is now $913 per person
$913
per person
found 1 day ago
Hotel Riu Plaza New York Times Square
4.0-star property

Hotel Riu Plaza New York Times Square

Aug 22 - Aug 25

3 night stay

Dallas (DAL) to Newark Liberty Intl. Airport (EWR)

Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,117, price is now $708 per person
$708
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from Dallas to Shelter Island
View all trips

Shelter Island premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
Arthouse Hotel New York City
4.0-star property

Arthouse Hotel New York City

8.8/10 Excellent! (2,013 reviews)

Aug 18 - Aug 22

4 night stay

San Juan (SJU) to New York (JFK)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Price was $1,106, price is now $794 per person
$794
per person
just found
Clean room, Air Conditioning and Professional Staff.

Reviewed on Jul 5, 2026

Hotel St. James
3.0-star property

Hotel St. James

8.8/10 Excellent! (7,502 reviews)

Aug 18 - Aug 22

4 night stay

San Juan (SJU) to New York (JFK)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Price was $1,229, price is now $804 per person
$804
per person
just found
Room has air conditioning and it’s cleaned daily.

Reviewed on Jul 5, 2026

INNSiDE by Meliá New York Nomad
4.5-star property

INNSiDE by Meliá New York Nomad

9.2/10 Wonderful! (2,240 reviews)

Aug 18 - Aug 22

4 night stay

San Juan (SJU) to Newark Liberty Intl. Airport (EWR)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Price was $1,347, price is now $936 per person
$936
per person
just found
Excellent and accommodating staff. Very clean and well appointed rooms.

Reviewed on Jul 5, 2026

Don't see what you're looking for?
See all available trips from San Juan to Shelter Island
View all trips

Shelter Island first class flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza New York Times Square
4.0-star property

Hotel Riu Plaza New York Times Square

9/10 Wonderful! (3,130 reviews)

Aug 15 - Aug 17

2 night stay

Chicago (ORD) to Newark Liberty Intl. Airport (EWR)

American Airlines • Roundtrip • FirstClass
Save 100% on your flight
Price was $761, price is now $526 per person
$526
per person
found 1 day ago
The breakfast was a nightmare; queuing to get in the restaurant and then the coffee machine was not working. When I eventually got a coffee and placed on my table, I then had to queue again for the self service buffet, I returned to find it had been cleared away and this happened on numerous occasions. Generally it was over populated and severely under staffed. Avoid

Reviewed on Jul 5, 2026

The Wall Street Hotel
5.0-star property

The Wall Street Hotel

9.6/10 Exceptional! (697 reviews)

Aug 12 - Aug 15

3 night stay

San Juan (SJU) to New York (JFK)

United • Roundtrip • FirstClass
Price was $2,238, price is now $1,497 per person
$1,497
per person
found 1 day ago
Great staff. Quiet and peaceful space. Perfect for relaxing after a day out in NYC.

Reviewed on Jul 1, 2026

Hotel Riu Plaza Manhattan Times Square
4.0-star property

Hotel Riu Plaza Manhattan Times Square

9.2/10 Wonderful! (3,652 reviews)

Aug 15 - Aug 17

2 night stay

Chicago (ORD) to Newark Liberty Intl. Airport (EWR)

American Airlines • Roundtrip • FirstClass
Save 100% on your flight
Price was $787, price is now $540 per person
$540
per person
found 1 day ago
💯

Reviewed on Jul 5, 2026

Don't see what you're looking for?
See all available trips from Chicago to Shelter Island
View all trips

Shelter Island

Why search for low cost fares on your flights to Shelter Island when Orbitz offers the guaranteed lowest prices on foreign and domestic flights? When you travel with Orbitz you can benefit from:

Bargain Flights to Shelter Island

Orbitz offers massive discounts and substantial last-minute savings on your Shelter Island flights. Orbitz ensures that you can find, plan and reserve your flights any destination with ease, all while enjoying the guaranteed lowest prices available anywhere.

Cutting-Edge Mobile Tools to Keep You In The Know

Orbitz sends you free alerts and updates on your Shelter Island flight wherever you are in the world. Once you have downloaded the free app for your iPhone, Android, or iPad, you can review or alter any travel plans that you have made or even book a future flight for business or pleasure. If you need to reserve a hotel room when booking your flight, you will find exclusive deals on our mobile site.

Frequent Flyer Program Enrolment

Orbitz finds you the lowest fares, but you can still add your miles to your frequent flyer program to earn miles or points on selected flights to Shelter Island. When making your booking, reference your frequent flyer number to receive discounts in the future.

Outstanding Customer Service

Orbitz values your business and wants to ensure that all of your flights are as easy as possible to book. If you have booked a flight to Shelter Island but need to cancel it, you may be able to do so online. If you have any questions or need help, the dedicated Orbitz customer service team is always standing by.

Frequently asked questions

How much is a flight to Shelter Island?
Travelers from near and far landed return-flight bargains ranging between $78 and $157 this week. Arriving from Raleigh (RDU)? The best one-way prices were just $41.
How to book the cheapest flight to Shelter Island?
Picking up cheap flights to Shelter Island is as easy as booking with Orbitz. But if you'd like to make sure you're walking away with the best flight deals around, here are some suggestions your wallet will love:

  • Consider departing from or arriving at alternative airports to save on your flight. Enter your preferred departure and arrival airports in the form fields, then click on the 'Nearby airports' function below. It will show you any available options.
  • If you're flexible with your travel schedule, click on the 'Show flexible dates' link. It'll display the flight deals for the days before and after your selected departure. Ticket prices often vary depending on what day of the week it is.
  • You can also hit the 'Show options' link to filter results for your preferred carrier, seating class, and nonstop and refundable flights. Under 'Sort & Filter' to the left, you can even pick the time of day you want to fly.
  • Once you've figured out your travel dates, don't delay booking your flight. Prices normally rise as the departure date gets closer.
  • Make even more savings on your trip by combining your hotel, flights and car rentals into a package. Your budget will thank you for it.
  • Flying during the busy season can mean pricey airfares. If possible, plan your vacation outside of popular dates, such as Thanksgiving, New Year's Eve and Easter.

What is the best time to book a flight to Shelter Island?
Book in January, February or August for the lowest airfares to Shelter Island. Once you've found a bargain, buy it — cheap flights tend to pop up and then vanish in the click of a mouse.
What day of the week is the cheapest to book a flight to Shelter Island?
Make a booking on a Tuesday, Wednesday or Saturday. Generally, these are the cheapest days to purchase fares to Shelter Island. The vacation of your dreams starts with a fantastic flight deal!
What is the cheapest day of the week to fly to Shelter Island?
According to Orbitz data from 2020, you should jump on a plane on a Monday to score cheap flights to Shelter Island. Next cheapest day? Tuesday. Saturday is the most expensive. So, leave early in the week if you'd like to book a wallet-friendly fare without paying premium prices.
What is the cheapest month to fly to Shelter Island?
To land cheap flights to Shelter Island, you should depart in August. If getting a great deal on your plane ticket is your top priority, Orbitz data has found that this is generally an excellent month to travel. June is when fares are at their highest.
Which airlines allow free cancellation?
We understand that plans change and flexibility is more important than ever. That's why you can search for flights that have free cancellation and no change fees on Orbitz. Just click on "Filter by flexible change policies" and we'll show you fares with more flexibility than a lip balm left in the sun!
What do I need for the flight to Shelter Island?
Whether you're a regular flyer or it's your first time on a plane, it helps to be organized when you travel. Here are a few tips and things to take into account:

  • Firstly, you'll need to take all applicable travel documents and your identification. How much is dependent on where you're flying from. When you book, always use the correct name, birth date and gender listed on your government-issued ID.
  • Fill your carry-on bag with snacks and things to keep you busy and you'll easily pass the time on this medium-haul flight. If possible, hop on the airport's Wi-Fi and transfer your favorite podcast or playlist to your device before take off.
  • Never mind what the season is at your destination, aircraft cabins can feel quite cool. Carry a sweater on your journey to stay warm and comfy.

How do I get cheap first-class/business deals to Shelter Island?
Experienced travelers know how to find business or first-class fares to Shelter Island without the sky-high price tag. Be like them with these handy tips:

  • Being flexible isn't just a yoga thing. Avoid locking in your travel dates so you can snap up more affordable airfares when a big sale comes along.
  • Look for a low-cost airline that has business-class seats. They usually come with extra space and a glass of Champagne — and a nicer price.
  • Make a bid for an upgrade. Some carriers hold online auctions that let you put down a price for a seat up the front. You may also be able to upgrade with points earned through a loyalty scheme.

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.