Title: $38 Cheap Flights to Cheshire, CT - Expedia.com ![Castle Craig at Hubbard Park, Meriden, CT. easily replaceable sky. with a clean, classic view of the tower. Very recognizable image of this historic structure.](https://images.trvl-media.com/place/183057/92c74fd9-1a45-4931-a43e-251e181e803f.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/183057/92c74fd9-1a45-4931-a43e-251e181e803f.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # $38 Cheap Flights to Cheshire, CT [View $38 flight on Sat, Apr 4, 2026](https://expedia.com/Flights-Search?trip=oneway&leg1=from:MCO,to:BDL,departure:4/4/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:37.98&airProductToken=AQowCi4IxnISBDE2ODQYzHAg4Vgo3beJAzCJuYkDOEVAAFgBagRQQ18xcgdLMjFTWFMyEgoIARABGAEqAkY5GAEiBAgBEAEoAigDMA0) [Cheshire Travel Guide](https://expedia.com/Cheshire.dx183057)[Hotels in Cheshire](https://expedia.com/Cheshire-Hotels.d183057.Travel-Guide-Hotels)[Things to do in Cheshire](https://expedia.com/Things-To-Do-In-Cheshire.d183057.Travel-Guide-Activities)[Car Rentals in Cheshire](https://expedia.com/Car-Rentals-In-Cheshire.d183057.Car-Rental-Guide)[Cheshire Vacation Packages](https://expedia.com/Cheshire.d183057.Destination-Travel-Guides) ## Popular airlines to Cheshire - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/30/landing_airline_sq_logo_MX.svg) Breeze Airways [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:Cheshire, Connecticut, United States of America,departure:3/28/2026TANYT&leg2=from:Cheshire, Connecticut, United States of America,to:CMH,departure:4/4/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"MX"}}]) ## How much is the cheapest flight to Cheshire? Prices were available within the past 7 days and start at $38 for one-way flights and $73 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Avelo Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/xp.gif) Sat, May 30 - Tue, Jun 9 MCO Orlando HVN New Haven $73 Roundtrip found 2 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MCO,to:HVN,departure:5/30/2026TANYT&leg2=from:HVN,to:MCO,departure:6/9/2026TANYT&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=AQo1CjMI2KABEgM3MTAYzHAgp20oy7OOAzDttI4DOEVAAFgBaghCQVNFRkFSRXIIRU5FN1dOQjEKNQozCNigARIDNzE5GKdtIMxwKLaejwMw4J-PAzhFQABYAWoIQkFTRUZBUkVyCEVMMjNXUEJDEgwICxABGAgqAlhQMgAYASIECAEQASgCMAM) ![Frontier Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/F9.gif) Fri, Jun 5 - Sat, Jun 13 MCO Orlando BDL Hartford $92 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MCO,to:BDL,departure:6/5/2026TANYT&leg2=from:BDL,to:MCO,departure:6/13/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:91.96&airProductToken=AQovCi0IxnISBDE2ODQYzHAg4Vgo8PSOAzCd9o4DOEtAAFgBagNFQ09yB0syMURYUzISCggBEAEYASoCRjkYASIECAEQASgCKAMoBDAB) ![Breeze Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/MX.gif) Wed, May 6 - Sun, May 10 MCO Orlando HVN New Haven $97 Roundtrip found 2 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MCO,to:HVN,departure:5/6/2026TANYT&leg2=from:HVN,to:MCO,departure:5/10/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:96.22&airProductToken=AQosCioIzbABEgM4MzAYzHAgp20ox6KMAzDxo4wDOENAAFgBagJOT3IFQ05PMDAKLAoqCM2wARIDODMxGKdtIMxwKMTTjAMw-NSMAzhBQABYAWoCTk9yBUFOTzAwEgoIARABGAEqAk1YGAEiBAgBEAEoAigDKAQwDQ) ![Southwest Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/wn.gif) Wed, May 13 - Mon, May 18 BWI Baltimore BDL Hartford $184 Roundtrip found 1 day ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BWI,to:BDL,departure:5/13/2026TANYT&leg2=from:BDL,to:BWI,departure:5/18/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:183.80&airProductToken=AQowCi4I15wBEgQzODQ1GMFFIOFYKOrujAMwuu-MAzhWQABYAWoDV0dBcgdWQk5WTjJECi8KLQjXnAESAzQ2NBjhWCDBRSjOpo0DMKinjQM4REAAWAFqA1dHQXIHRFpOVk4yRBIKCAEQARgBKgJXThgBIgQIARABKAIoAygEMAE) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Sat, Jun 6 - Tue, Jun 9 MCO Orlando BDL Hartford $187 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MCO,to:BDL,departure:6/6/2026TANYT&leg2=from:BDL,to:MCO,departure:6/9/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:186.80&airProductToken=AQouCiwIwmwSAzQzOBjMcCDhWCjxgo8DMJ6EjwM4TEAAWAFqAkROcghQSTJRVVNMMQouCiwIwmwSAzczNxjhWCDMcCiYno8DMMWfjwM4TEAAWAFqAkROcghQSTJRVVNMMRIKCAEQARgBKgJCNhgBIgQIARABKAIoBCgGMAE) ## Alternative airports near Cheshire 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:BDL,departure:3/28/2026TANYT&leg2=from:BDL,to:CMH,departure:3/29/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) BDL Bradley Intl. Cheapest 51 min [Flights from $378 ](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:BDL,departure:3/28/2026TANYT&leg2=from:BDL,to:CMH,departure:3/29/2026TANYT&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_) ## Frequently asked questions ### What month is the cheapest to fly to Cheshire? ### Which US cities have the cheapest flights to Cheshire? ### Which US cities fly direct to Cheshire? > - Washington > - Chicago > - Orlando > - Atlanta > - Charlotte ### How to find a cheap flight to Cheshire? ### How to get a cheap last-minute flight to Cheshire? ### How far in advance should I book a flight to Cheshire? ### Which day of the week is the cheapest day to buy a plane ticket to Cheshire? ### Which airlines fly to Cheshire? > - Delta Air Lines > - American Airlines > - United Airlines > - JetBlue Airways ### Where do you fly into Cheshire? ### How far is the airport from central Cheshire? ### Can I save money by booking a Cheshire trip package? ### Can I change or cancel my flight to Cheshire? \*Flight schedules are subject to change. ## Book with confidence # Tips to find the cheapest flights to Cheshire **The cheapest day to fly** Get started finding a cheap flight to Cheshire 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** May is the cheapest month to fly to Cheshire. 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 Cheshire. 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 Cheshire, 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 Cheshire** The lowest price for round-trip flights to Cheshire in 2026 starts from from $73, while one-way tickets start from from $38\. 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 Cheshire. If you have a preferred departure time or airline, you can use the handy filters to customize your search. **The cheapest airlines flying to Cheshire** Frontier Airlines, Avelo Airlines, Breeze Airways, Southwest Airlines, JetBlue Airways are just some of the airlines that can typically offer cheap tickets to Cheshire. 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 Cheshire and countless more destinations worldwide. **The most affordable airports to fly into** To view the cheapest airports to fly into for Cheshire, 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 Cheshire. 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 Cheshire 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 Cheshire** 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 Cheshire. **Stopover savings** The cheapest tickets to Cheshire are sometimes those with a stopover. Book one of these flights, and you'll change planes at an airport en route to Cheshire. 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 Cheshire 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 Cheshire. Simply download the free Expedia app to your smart device and activate Cheshire 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 Cheshire. 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. ## Travel information | Destination airport | Tweed - New Haven Regional | | ----------------------------- | -------------------------- | | Destination airport IATA code | HVN | | Destination city name | New Haven | | Roundtrip price | $73 | ## Trending flights to Cheshire Prices were available within the past 7 days and start at $38 for one-way flights and $73 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Avelo Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/xp.gif) Sat, May 30 - Tue, Jun 9 MCO Orlando HVN New Haven $73 Roundtrip found 2 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MCO,to:HVN,departure:5/30/2026TANYT&leg2=from:HVN,to:MCO,departure:6/9/2026TANYT&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=AQo1CjMI2KABEgM3MTAYzHAgp20oy7OOAzDttI4DOEVAAFgBaghCQVNFRkFSRXIIRU5FN1dOQjEKNQozCNigARIDNzE5GKdtIMxwKLaejwMw4J-PAzhFQABYAWoIQkFTRUZBUkVyCEVMMjNXUEJDEgwICxABGAgqAlhQMgAYASIECAEQASgCMAM) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Hotels near Maplecroft Plaza Shopping Center ](https://www.expedia.com/Maplecroft-Plaza-Shopping-Center-Hotels.0-l553248621557931242-0.Travel-Guide-Filter-Hotels) - [B&B in Cheshire Historic District ](https://www.expedia.com/Cheshire-Historic-District-Bed-And-Breakfast.d6346724-aaBedAndBreakfast.Travel-Guide-Accommodation) - 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