Title: $34 Cheap Flights to Chester, CT - Expedia.com ![Mystic, Stonington, Connecticut, United States - October 26, 2018: Panoramic view of old historic homes by the Mystic River during a vibrant sunrise.](https://images.trvl-media.com/place/183058/f457b867-7f08-4489-b983-3426d68ada3d.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/183058/f457b867-7f08-4489-b983-3426d68ada3d.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # $34 Cheap Flights to Chester, CT [View $34 flight on Tue, Jun 9, 2026](https://expedia.com/Flights-Search?trip=oneway&leg1=from:MCO,to:HVN,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:33.95&airProductToken=AQo1CjMI2KABEgM3MTgYzHAgp20okqCPAzC0oY8DOEVAAFgBaghCQVNFRkFSRXIIRUwyM1dQQkMSCggLEAEYCCoCWFAYASIECAEQASgCMAM) - [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 [Chester Travel Guide](https://expedia.com/Chester.dx183058)[Hotels in Chester](https://expedia.com/Chester-Hotels.d183058.Travel-Guide-Hotels)[Car Rentals in Chester](https://expedia.com/Car-Rentals-In-Chester.d183058.Car-Rental-Guide)[Chester Vacation Packages](https://expedia.com/Chester.d183058.Destination-Travel-Guides) ## Popular airlines to Chester - ![](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:Chester, Connecticut, United States of America,departure:3/13/2026TANYT&leg2=from:Chester, Connecticut, United States of America,to:CMH,departure:3/20/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"MX"}}]) - ![](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 Chester? Prices were available within the past 7 days and start at $34 for one-way flights and $68 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) Tue, Jun 2 - Tue, Jun 9 MCO Orlando HVN New Haven $68 Roundtrip found 4 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MCO,to:HVN,departure:6/2/2026TANYT&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:67.90&airProductToken=AQo1CjMI2KABEgM3MTgYzHAgp20ostGOAzDU0o4DOEVAAFgBaghCQVNFRkFSRXIIRUwyM1dQQkMKNQozCNigARIDNzE5GKdtIMxwKLaejwMw4J-PAzhFQABYAWoIQkFTRUZBUkVyCEVMMjNXUEJDEgoICxABGAgqAlhQGAEiBAgBEAEoAjAD) ![Breeze Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/MX.gif) Tue, Jun 2 - Tue, Jun 9 MCO Orlando HVN New Haven $72 Roundtrip found 4 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MCO,to:HVN,departure:6/2/2026TANYT&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:71.22&airProductToken=AQosCioIzbABEgMyNDYYzHAgp20o8NGOAzCa044DOEFAAFgBagJOT3IFQU5PMDAKLAoqCM2wARIDMjQ3GKdtIMxwKKeijwMw26OPAzhBQABYAWoCTk9yBUFOTzAwEgoIARABGAEqAk1YGAEiBAgBEAEoAigDKAQwDQ) ![Avelo Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/xp.gif) Tue, Jun 2 - Sat, Jun 6 MCO Orlando HVN New Haven $73 Roundtrip found 5 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MCO,to:HVN,departure:6/2/2026TANYT&leg2=from:HVN,to:MCO,departure:6/6/2026TANYT&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=AQo1CjMI2KABEgM3MTgYzHAgp20ostGOAzDU0o4DOEVAAFgBaghCQVNFRkFSRXIIRUwyM1dQQkMKNQozCNigARIDNzExGKdtIMxwKMqAjwMw9IGPAzhFQABYAWoIQkFTRUZBUkVyCEVORTdXTkIxEgwICxABGAgqAlhQMgAYASIECAEQASgCMAM) ![Avelo Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/xp.gif) Tue, Mar 10 - Wed, Mar 11 RDU Raleigh HVN New Haven $75 Roundtrip found 3 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:RDU,to:HVN,departure:3/10/2026TANYT&leg2=from:HVN,to:RDU,departure:3/11/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:74.83&airProductToken=AQo2CjQI2KABEgM2NzYY8aABIKdtKNWjhwMwt6SHAzhWQABYAWoIQkFTRUZBUkVyCFZORTdXTkIxCjYKNAjYoAESAzM3NxinbSDxoAEohq2HAzDurYcDOEVAAFgBaghCQVNFRkFSRXIIRU5FN1dOQjESCggLEAEYCCoCWFAYASIECAEQASgCMAM) ![Breeze Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/MX.gif) Sat, Jun 6 - Tue, Jun 9 MCO Orlando HVN New Haven $77 Roundtrip found 13 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MCO,to:HVN,departure:6/6/2026TANYT&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:76.22&airProductToken=AQosCioIzbABEgM4MzAYzHAgp20op_-OAzDRgI8DOEFAAFgBagJOT3IFQU5PMDASCggBEAEYASoCTVgYASIECAEQASgCKAMoBDAN) ![](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 Chester? ### Which US cities have the cheapest flights to Chester? ### Which US cities fly direct to Chester? > - Washington > - Chicago > - Orlando > - Atlanta > - Charlotte ### How to find a cheap flight to Chester? ### How to get a cheap last-minute flight to Chester? ### How far in advance should I book a flight to Chester? ### Which day of the week is the cheapest day to buy a plane ticket to Chester? ### Which airlines fly to Chester? > - Delta Air Lines > - American Airlines > - United Airlines > - JetBlue Airways ### Where do you fly into Chester? ### How far is the airport from central Chester? ### Can I save money by booking a Chester trip package? ### Can I change or cancel my flight to Chester? \*Flight schedules are subject to change. ## Book with confidence # Tips to find the cheapest flights to Chester **The cheapest day to fly** Get started finding a cheap flight to Chester 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** June is the cheapest month to fly to Chester. 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 Chester. 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 Chester, 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 Chester** The lowest price for round-trip flights to Chester in 2026 starts from from $68, while one-way tickets start from from $34\. 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 Chester. If you have a preferred departure time or airline, you can use the handy filters to customize your search. **The cheapest airlines flying to Chester** Avelo Airlines, Breeze Airways are just some of the airlines that can typically offer cheap tickets to Chester. 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 Chester and countless more destinations worldwide. **The most affordable airports to fly into** To view the cheapest airports to fly into for Chester, 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 Chester. 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 Chester 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 Chester** 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 Chester. **Stopover savings** The cheapest tickets to Chester are sometimes those with a stopover. Book one of these flights, and you'll change planes at an airport en route to Chester. 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 Chester 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 Chester. Simply download the free Expedia app to your smart device and activate Chester 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 Chester. 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 | $68 | ## Trending flights to Chester Prices were available within the past 7 days and start at $34 for one-way flights and $68 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) Tue, Jun 2 - Tue, Jun 9 MCO Orlando HVN New Haven $68 Roundtrip found 4 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MCO,to:HVN,departure:6/2/2026TANYT&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:67.90&airProductToken=AQo1CjMI2KABEgM3MTgYzHAgp20ostGOAzDU0o4DOEVAAFgBaghCQVNFRkFSRXIIRUwyM1dQQkMKNQozCNigARIDNzE5GKdtIMxwKLaejwMw4J-PAzhFQABYAWoIQkFTRUZBUkVyCEVMMjNXUEJDEgoICxABGAgqAlhQGAEiBAgBEAEoAjAD) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Hotels near Chester Center ](https://www.expedia.com/Chester-Center-Chester-Hotels.0-n553248635976479536-0.Travel-Guide-Filter-Hotels) - [Hotels near Norma Terris Theater ](https://www.expedia.com/Norma-Terris-Theater-Hotels.0-l553248621532665705-0.Travel-Guide-Filter-Hotels) - 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