Title: $25 Cheap Flights to Sheffield Island, CT - Expedia.com ![A nice spot for a picnic and a stroll along the beach. ](https://images.trvl-media.com/place/9245/c630a679-4303-4d4f-b558-8074390c35c3.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Richard Miska ![](https://images.trvl-media.com/place/9245/c630a679-4303-4d4f-b558-8074390c35c3.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # $25 Cheap Flights to Sheffield Island, CT [View $25 flight on Wed, Mar 4, 2026](https://expedia.com/Flights-Search?trip=oneway&leg1=from:MCO,to:LGA,departure:3/4/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:24.39&airProductToken=AQotCisIzpYBEgM5MzAYzHAgywEo3-CGAzD84YYDOFBAAFgBagJSUHIGUEExNE5SEgoIARABGAEqAk5LGAEiBAgBEAEoAigDKAQwDQ) - [Roundtrip](?flightType=roundtrip) - [One-way](?flightType=oneway) - [Multi-city](?flightType=multicity) ### Travelers Adults ChildrenAges 2 to 17 InfantsYounger than 2 EconomyPremium economyBusiness classFirst class Leaving from Going to Departing Returning Add a place to stay Add a car Direct flights only [Sheffield Island Travel Guide](https://expedia.com/Sheffield-Island.dx6353650)[Hotels in Sheffield Island](https://expedia.com/Sheffield-Island-Hotels.d6353650.Travel-Guide-Hotels)[Car Rentals in Sheffield Island](https://expedia.com/Car-Rentals-In-Sheffield-Island.d6353650.Car-Rental-Guide)[Sheffield Island Vacation Packages](https://expedia.com/Sheffield-Island.d6353650.Destination-Travel-Guides) ## Popular airlines to Sheffield Island - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AA.svg) American Airlines [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:Sheffield Island, Connecticut, United States of America,departure:2/27/2026TANYT&leg2=from:Sheffield Island, Connecticut, United States of America,to:CMH,departure:3/6/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_UA.svg) United [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:Sheffield Island, Connecticut, United States of America,departure:2/27/2026TANYT&leg2=from:Sheffield Island, Connecticut, United States of America,to:CMH,departure:3/6/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_WN.svg) Southwest Airlines [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:Sheffield Island, Connecticut, United States of America,departure:2/27/2026TANYT&leg2=from:Sheffield Island, Connecticut, United States of America,to:CMH,departure:3/6/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_DL.svg) Delta [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:Sheffield Island, Connecticut, United States of America,departure:2/27/2026TANYT&leg2=from:Sheffield Island, Connecticut, United States of America,to:CMH,departure:3/6/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_F9.svg) Frontier Airlines [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:Sheffield Island, Connecticut, United States of America,departure:2/27/2026TANYT&leg2=from:Sheffield Island, Connecticut, United States of America,to:CMH,departure:3/6/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"F9"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_B6.svg) JetBlue Airways [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:Sheffield Island, Connecticut, United States of America,departure:2/27/2026TANYT&leg2=from:Sheffield Island, Connecticut, United States of America,to:CMH,departure:3/6/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"B6"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AS.svg) Alaska Airlines [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:Sheffield Island, Connecticut, United States of America,departure:2/27/2026TANYT&leg2=from:Sheffield Island, Connecticut, United States of America,to:CMH,departure:3/6/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AS"}}]) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__notification.svg) ### Be in the know Get alerts if flight prices drop or rise\* - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Book smarter Save up to 30% on select hotels after you book a flight\* - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__trophy.svg) ### Earn twice Earn your airline miles on top of our OneKeyCash [Learn about One Key](https://www.expedia.com/welcome-one-key) ## How much is the cheapest flight to Sheffield Island? Prices were available within the past 7 days and start at $25 for one-way flights and $52 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Sat, Feb 28 - Tue, Mar 3 MCO Orlando LGA New York $52 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MCO,to:LGA,departure:2/28/2026TANYT&leg2=from:LGA,to:MCO,departure:3/3/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:51.02&airProductToken=AQotCisIzpYBEgM2NTgYzHAgywEoxq-GAzDgsIYDOFBAAFgBagJSUHIGUEExNE5SCi0KKwjOlgESAzkwMBjLASDMcCiy0IYDMObRhgM4UEAAWAFqAlJQcgZQQTE0TlISDAgBEAEYASoCTksyABgBIgQIARABKAIoAygEMA0) ![Frontier Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/F9.gif) Fri, Feb 27 - Sun, Mar 1 MCO Orlando ISP Islip $56 Roundtrip found 5 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MCO,to:ISP,departure:2/27/2026TANYT&leg2=from:ISP,to:MCO,departure:3/1/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:55.96&airProductToken=AQowCi4IxnISBDM5NDIYzHAgyHwo2aKGAzD2o4YDOEVAAFgBagRQQ18xcgdLMTREWFMyCjAKLgjGchIEMzk0MRjIfCDMcCjtuoYDMKm8hgM4RUAAWAFqBFBDXzFyB0sxNERYUzISDAgBEAEYASoCRjkyABgBIgQIARABKAIoAzAN) ![Avelo Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/xp.gif) Tue, May 19 - Mon, May 25 MCO Orlando HVN New Haven $73 Roundtrip found 13 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MCO,to:HVN,departure:5/19/2026TANYT&leg2=from:HVN,to:MCO,departure:5/25/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:72.55&airProductToken=AQo1CjMI2KABEgM3MTgYzHAgp20o8rONAzCUtY0DOEVAAFgBaghCQVNFRkFSRXIIRUwyM1dQQkMKNQozCNigARIDNzE3GKdtIMxwKM72jQMw-PeNAzhFQABYAWoIQkFTRUZBUkVyCEVORTdXTkIxEgoICxABGAgqAlhQGAEiBAgBEAEoAjAD) ![Breeze Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/MX.gif) Thu, Mar 5 - Sun, Mar 8 MCO Orlando HVN New Haven $82 Roundtrip found 2 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MCO,to:HVN,departure:3/5/2026TANYT&leg2=from:HVN,to:MCO,departure:3/8/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:81.22&airProductToken=AQosCioIzbABEgM4MzAYzHAgp20o-OuGAzCg7YYDOEFAAFgBagJOT3IFQU5PMDAKLAoqCM2wARIDODMxGKdtIMxwKOyOhwMwq5CHAzhBQABYAWoCTk9yBUFOTzAwEgoIARABGAEqAk1YGAEiBAgBEAEoAigDKAQwDQ) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Thu, Apr 30 - Mon, May 4 MCO Orlando LGA New York $127 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MCO,to:LGA,departure:4/30/2026TANYT&leg2=from:LGA,to:MCO,departure:5/4/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:126.80&airProductToken=AQozCjEIwYIBEgQzMTIzGMxwIMsBKKjgiwMwyeGLAzhCQABYAWoFQkFTSUNyCE9XRFpJTkJYCjMKMQjBggESBDIzNDMYywEgzHAo8omMAzCgi4wDOEJAAFgBagVCQVNJQ3IIT1dEWklOQlgSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL) ## Alternative airports near Sheffield Island Prices were available within the past 7 days. Prices and availability are subject to change. [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:LGA,departure:2/27/2026TANYT&leg2=from:LGA,to:CMH,departure:3/9/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) LGA LaGuardia Cheapest [Flights from $214 ](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:LGA,departure:2/27/2026TANYT&leg2=from:LGA,to:CMH,departure:3/9/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:HPN,departure:2/27/2026TANYT&leg2=from:HPN,to:CMH,departure:3/14/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) HPN Westchester County [Flights from $224 ](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:HPN,departure:2/27/2026TANYT&leg2=from:HPN,to:CMH,departure:3/14/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:ISP,departure:2/27/2026TANYT&leg2=from:ISP,to:CMH,departure:3/15/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) ISP MacArthur [Flights from $689 ](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:ISP,departure:2/27/2026TANYT&leg2=from:ISP,to:CMH,departure:3/15/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=FTG_SPRING_PROMO_) ## Tips to find the cheapest flights to Sheffield Island **The cheapest day to fly** Get started finding a cheap flight to Sheffield Island on Expedia by either choosing a deal on this page or entering into the search bar your travel dates, origin airport, and whether you want roundtrip or one-way airfare. You can filter for flexibility, number of stops, airline, and departure/arrival times to find the best flight for you. **The cheapest month to fly** February is the cheapest month to fly to Sheffield Island. This coincides with the low season when fewer people travel. Whichever month you travel in, though, be sure to book at least a month in advance if you want to score cheap tickets to Sheffield Island. ARC's data shows that domestic flights booked 28 days or more before departure are typically 24% cheaper than those booked last minute. **The most affordable time to book a flight** Typically, a Sunday can be the cheapest time to book a flight to Sheffield Island, according to ARC’s data. On average, you could save between 6% and 13% by booking on a Sunday instead of a Friday, which is the most expensive day to make a reservation. **The cheapest round-trip tickets to Sheffield Island** The lowest price for round-trip flights to Sheffield Island in 2026 starts from from $52, while one-way tickets start from from $25\. Expedia's effective search tool is one of the best ways to find a budget airfare. Simply enter your dates, and within seconds, it'll show you a vast selection of the cheapest flights to Sheffield Island. If you have a preferred departure time or airline, you can use the handy filters to customize your search. **The cheapest airlines flying to Sheffield Island** Spirit Airlines, Frontier Airlines, Avelo Airlines, Breeze Airways, JetBlue Airways, American Airlines are just some of the airlines that can typically offer cheap tickets to Sheffield Island. You can find their most affordable flights by using the “airline” search filter and then sorting prices from low to high. As a trusted partner of the world's leading airlines, Expedia offers you some of the best airfare deals to Sheffield Island and countless more destinations worldwide. **The most affordable airports to fly into** To view the cheapest airports to fly into for Sheffield Island, simply order your search results from lowest to highest price. Expedia's search tool compares flight prices for all airports close to your destination, so you don't have to manually search them one by one to find the cheapest flight to Sheffield Island. If you have a preferred place to fly into, take advantage of the “arrival airport” filter to narrow down your search on Expedia. **Save with a package** With Expedia's amazing [package deals](https://www.expedia.com/package-deals), you could save hundreds of dollars by booking your Sheffield Island plane tickets together with your accommodations, car rental, or activities. Just select the search wizard's “package” option to view some of the cheapest deals. Look out for the green savings label to see how much you're saving. **Date flexibility for the cheapest flights to Sheffield Island** If you can be flexible with your travel dates, it's a good idea to broaden your search by comparing prices on different days. This will open up more options, meaning you could uncover a less expensive flight to Sheffield Island. **Stopover savings** The cheapest tickets to Sheffield Island are sometimes those with a stopover. Book one of these flights, and you'll change planes at an airport en route to Sheffield Island. While the overall travel time might be longer than a non-stop flight, you may decide it's worth it for the money saved. **Get Expedia's Price Drop Protection** Price Drop Protection means that if your flight gets cheaper after booking, you'll be credited the difference\*. This gives you peace of mind that you're getting one of the cheapest flights to Sheffield Island for your chosen departure. Expedia's Price Drop Protection is available for a small fee but is free to One Key Gold and Platinum tier members. \*Terms apply. **Use our Price Tracking feature** Expedia's Price Tracking feature is another great tool that removes the guesswork from finding cheap flights to Sheffield Island. Simply download the free Expedia app to your smart device and activate Sheffield Island flight price alerts for your travel dates. There's even a price predictor tool that uses historical data to indicate the best time to book, giving you peace of mind that you'll nab the lowest prices. **Book with Expedia** As well as Price Drop Protection and Price Tracking, Expedia's close partnership with a vast selection of the world's leading airlines means you're sure to find cheap flights to Sheffield Island. Plus, the One Key rewards program lets you earn real cash rewards on most bookings that you can use to save money on future trips. Best of all, it's free to join, and members often unlock exclusive discounts, too. Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023\. The percentages you see are averages. ## Frequently asked questions ### What month is the cheapest to fly to Sheffield Island? ### Which US cities have the cheapest flights to Sheffield Island? ### Which US cities fly direct to Sheffield Island? > - Los Angeles > - San Francisco > - Boston > - Miami > - Orlando ### How to find a cheap flight to Sheffield Island? ### How to get a cheap last-minute flight to Sheffield Island? ### How far in advance should I book a flight to Sheffield Island? ### Which day of the week is the cheapest day to buy a plane ticket to Sheffield Island? ### Which airlines fly to Sheffield Island? > - Delta Air Lines - 4,784 flights to Sheffield Island each month, including 4,784 flights to John F. Kennedy Intl. Airport (JFK) per month. > - JetBlue Airways - 2,856 flights to Sheffield Island each month, including 2,856 flights to John F. Kennedy Intl. Airport (JFK) per month. > - American Airlines - 1,967 flights to Sheffield Island each month, including 1,967 flights to John F. Kennedy Intl. Airport (JFK) per month. ### Where do you fly into Sheffield Island? ### Can I save money by booking a Sheffield Island trip package? ### Can I change or cancel my flight to Sheffield Island? \*Flight schedules are subject to change. __Flights to Sheffield Island information__ | Destination airport | LaGuardia | | ----------------------------- | --------- | | Destination airport IATA code | LGA | | Destination city name | New York | | Roundtrip price | $51 | ## Trending flights to Sheffield Island Prices were available within the past 7 days and start at $25 for one-way flights and $52 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Sat, Feb 28 - Tue, Mar 3 MCO Orlando LGA New York $52 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MCO,to:LGA,departure:2/28/2026TANYT&leg2=from:LGA,to:MCO,departure:3/3/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:51.02&airProductToken=AQotCisIzpYBEgM2NTgYzHAgywEoxq-GAzDgsIYDOFBAAFgBagJSUHIGUEExNE5SCi0KKwjOlgESAzkwMBjLASDMcCiy0IYDMObRhgM4UEAAWAFqAlJQcgZQQTE0TlISDAgBEAEYASoCTksyABgBIgQIARABKAIoAygEMA0) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Hotels near Sheffield Island Lighthouse ](https://www.expedia.com/Sheffield-Island-Lighthouse-Hotels.0-l553248621558114961-0.Travel-Guide-Filter-Hotels) - [Rowayton Hotels ](https://www.expedia.com/Rowayton-Hotels.d3000430454.Travel-Guide-Hotels) - 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