$35 Find Cheap Flights to Chester

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chester departing on 5/30. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
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Cheap Flight Deals to Chester

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights to Chester that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals to Chester

KAYAK's recommended round-trip deals from the most popular airlines that fly to Chester.
Discover the best prices for you by selecting your travel dates on KAYAK.
Avelo Airlines Logo
9:03 pm - 10:14 pmIAD-HVN
1h 11mnonstop
Avelo Airlines Logo
7:00 pm - 8:17 pmHVN-IAD
1h 17mnonstop
$70Avelo Airlines
Find Deal
Fri, Jun 6 - Mon, Jun 9
Avelo Airlines Logo
7:25 am - 9:01 amRDU-HVN
1h 36mnonstop
Avelo Airlines Logo
3:20 pm - 4:59 pmHVN-RDU
1h 39mnonstop
$70Avelo Airlines
Find Deal
Thu, Jun 5 - Fri, Jun 6
Avelo Airlines Logo
9:05 pm - 10:16 pmIAD-HVN
1h 11mnonstop
Avelo Airlines Logo
7:10 pm - 8:37 pmHVN-IAD
1h 27mnonstop
$77Avelo Airlines
Find Deal
Fri, May 30 - Mon, Jun 30
Breeze Airways Logo
7:41 pm - 10:28 pmMCO-HVN
2h 47mnonstop
Breeze Airways Logo
8:00 am - 11:00 amHVN-MCO
3h 00mnonstop
$78Breeze Airways
Find Deal
Tue, May 13 - Tue, May 20
Avelo Airlines Logo
11:13 am - 2:06 pmPBI-HVN
2h 53mnonstop
Avelo Airlines Logo
3:35 pm - 6:33 pmHVN-PBI
2h 58mnonstop
$78Avelo Airlines
Find Deal
Thu, Jun 5 - Sun, Jun 8
Breeze Airways Logo
11:55 am - 2:50 pmPBI-HVN
2h 55mnonstop
Breeze Airways Logo
8:00 am - 11:10 amHVN-PBI
3h 10mnonstop
$79Breeze Airways
Find Deal
Sat, May 31 - Sat, Jun 7
Breeze Airways Logo
6:00 am - 8:47 amMCO-HVN
2h 47mnonstop
Breeze Airways Logo
6:30 pm - 9:30 pmHVN-MCO
3h 00mnonstop
$79Breeze Airways
Find Deal
Fri, May 16 - Mon, May 19
Avelo Airlines Logo
9:05 pm - 10:16 pmIAD-HVN
1h 11mnonstop
Avelo Airlines Logo
7:00 pm - 8:17 pmHVN-IAD
1h 17mnonstop
$79Avelo Airlines
Find Deal
Fri, May 30 - Mon, Jun 2
Avelo Airlines Logo
8:10 am - 9:46 amRDU-HVN
1h 36mnonstop
Avelo Airlines Logo
4:50 pm - 6:29 pmHVN-RDU
1h 39mnonstop
$79Avelo Airlines
Find Deal
Thu, May 22 - Sun, May 25
 Logo
8:10 am - 9:46 amRDU-HVN
1h 36mnonstop
 Logo
8:00 am - 9:53 amHVN-RDU
1h 53mnonstop
Thu, May 22 - Mon, May 26
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Good to know - Book Cheap Chester Plane Tickets

Low seasonJanuary
High seasonAugust
Cheapest flight$35
Best time to beat the crowds with an average 28% drop in price.
Most popular time to fly with an average 9% increase in price.
Flight from Raleigh to New Haven

FAQs - booking Chester flights

  • How long is the flight to Chester?

    Flights from West Palm Beach2h 53m
    Flights from Jacksonville2h 30m
    Flights from Tampa2h 55m
    Flights from Orlando2h 51m
    Flights from Raleigh1h 39m
  • What is the cheapest flight to New Haven?

    In the last 3 days, the cheapest flight deal to New Haven was found on the route from Raleigh, at $70 return. The most popular connection is from Orlando to New Haven and KAYAK users have found round-trip deals for as low as $78 in the last 3 days.

  • How to fly to Chester?

    You cannot fly directly to Chester. KAYAK recommends you fly to Tweed-New Haven (HVN) (22.83 miles from Chester). From there you can rent a car or get a taxi.

  • What airports are near Chester?

    The closest airport is Tweed-New Haven (HVN) (22.83 mi). Other nearby airports are Hartford Bradley Intl (BDL) (38.51 mi) or Islip Long Island (ISP) (53 mi). KAYAK recommends you fly to Tweed-New Haven.

  • How far is Tweed-New Haven Airport from central New Haven?

    There are 4 miles between New Haven city center and Tweed-New Haven Airport.

  • What is the name of New Haven’s airport?

    All flights to New Haven land at Tweed-New Haven Airport. The airport code is HVN,and it can also be referred to as New Haven or Tweed-New Haven.

  • How does KAYAK find such low prices on flights to Chester?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights to Chester.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket to Chester?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chester is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights to Chester?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chester with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight to Chester?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chester up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Chester

  • There is no major airport in Chester. It is instead served by Tweed-New Haven Airport.
  • Looking for a cheap flight? 25% of our users found flights on this route for $42 or less one-way and $98 or less round-trip.
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chester flight deals.

Top 3 airlines flying to Chester

Need help choosing which airline to fly with from the United States to Chester? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.1
Breeze AirwaysOverall score based on 160 reviews
6.7Food
8.2Comfort
8.8Crew
6.6Entertainment
8.3Boarding
Airline reviews

Plane did no snacks and had no wifi or entertainment although the flight was 4 hours long.

8.0 ExcellentAnonymous, Apr 2025PVU - IAD
Read more Breeze Airways reviews

Plane did no snacks and had no wifi or entertainment although the flight was 4 hours long.

My original booking was a nonstop flight. It got changed to a flight with a 6vhour layover that became a 7+ hour lay over. I'll never fly this airline again after this roundtrip is over.

I was surprised at how wonderful it was. The aircraft was clean. The crew was warm and welcoming and as a result the passengers were friendly. One warning the only free thing was water. I kind of liked picking wet hat I was willing to pay for and what I was willing to skip.

The flight wasn’t big on frills, which is fine with me. I flew into Islip MacArthur Airport, which saved me from having to go through LaGuardia to visit friends on Long Island. It was inexpensive and super convenient!

Great experience! This was my first time flying with them and I could not have been happier.

Airplane was newer and very clean, lots of space. Crew was great. There was no food and entertainment but that was expected so not an issue.

I like that the price is right! The airplane is clean and the staff is friendly. We landed safely, so that is always a gold star in my book! Great job!

Purposely delayed the flight by 2 hours and 58 minutes so that they would not have to give me the FAA mandated refund for a delay of 3 hours. Offered flight credit instead. All that is offered on board is water and coffee, everything else costs money. They charge you for carry on and checked bags. Would not fly again.

nice flight. no frills but a 3 hour flight I caught up on my sleep. Stan O

First time flying Breeze, was very impressed. I will use Breeze again.

Expect nothing and you will be fine. Seats are crammed.

Terrible landing. Uncomfortable seats. Great cabin crew-helpful and pleasant!

Tight fit in middle seat but OK for short flight. Crew was more interested in talking to each other than helping passengers - strickingly dissappointing. DAB is a great airport. New Haven sucks! Excellent value for the .

Avelo is definitely a budget airline and you get what you pay for. The plane was packed and the seats were not particularly comfortable. Staff was very nice and both of our flights were on time. The one thing I wish I had known was that the staff does not show up at the airport desk to check your bags until two hours before the flight. We had a 4:30 flight and had to check out of our hotel at noon. Since we have lounge passes we planned to check our bag, go through security and hang out at the lounge until we had to board. But because we could not check our bag until 2:30, when the staff showed up, we could not go through security and access the lounge. Passengers with boarding passes and carry on luggage would not have this issue. I might fly Avelo again but would only do carry on or plan to get to the airport no sooner than two hours before check in. And I would not recommend a long flight on Avelo since there is no food or entertainment and the seats are not comfortable.

No food or entertainment, but flight very comfortable and on time.

Baggage claim was barbaric at Wilmington. I realize that this is a startup airline but if they hope to grow or even survive they need to upgrade this airport. There is no automated luggage carousel and at times you are not only fighting your fellow passengers to get to your bags but also passengers coming in from other flights who cross right in front of you

No frills, i.e., no drinks or snacks. One is charged for everything. The cost really adds up. The crew and flight attendants were excellent and very pleasant.

I always walk by a pallet of Avelo branded mini bottles of water on the tarmac, but I’ve never seen them in flight. Yup, not even water offered on a 3 hour flight. No wi-fi onboard. We just watch the flight crew on their phone for 3 hours every flight. At least a mid-flight trash pickup would be great. Better than my last flight, but they only could have gone up from there. Don’t use for business or ticketed vacation like Disney… too unreliable.

You get what you pay for. The plane was dirty and the seats were awful.

Nightmare airline. Avoid Avelo. Understaffed at check-in with long, slow lines. Inexplicably had two flights and only one plane. Not weather or maintenance related apparently. One was supposed to go to Myrtle Beach and one to Orlando. I imagine someone thought it would be better to fly the available plane to Myrtle Beach and back and then go to Orlando since that round-trip was shorter. This didn’t account for the human factor of an end-of-week Orlando flight being 85% Disney passengers and putting the flight on a six-hour delay in New Haven airport… which, if you’ve been there, is tiny and has nothing to do for 50 kids excited to get to Disney. This delay was announced at the time of departure. No one realized before the time of departure there was no plane on the ground? And no one thought… hey I think the Myrtle Beach crowd might be a better one to have wait if we’re going to make a choice here (mind you the initial inbound plane was coming from Orlando and supposed to be out aircraft… they literally said let just grab this plane because it’s here to get this other group out at the last second). There is/was zero customer service desk for Avelo in HVN and there were no updates/announcements throughout the day. Plane still gets back late and we finally leave. No wi-fi on these planes, no snack or even water. I know this is budget airline, but expected at least a water after 8 hours of travel day. This should have been offered in terminal too. We land… hooray. Would you believe there is no ground crew to get the plane in to the gate… for 27 minutes. 27 minutes!!! At this point the rental car center is closing in 10 minutes, kids on the plane are crying again, and everyone is talking about how they’re never flying Avelo again. Finally get off. Bags are out at baggage claim right away (finally something right?), but they’ve stopped the carousel immediately and there is no baggage service rep. People are climbing over the carousel to get to the far side (if you’ve ever been to MCO you’ve seen it) because obviously they just stopped it immediately once all the bags were out. This airline is a dumpster fire. Icing on the cake was that while everyone was stuck in HVN, they were setting up for a celebration of their millionth passenger tomorrow. I bet 995,000 of those will never fly the airline again. Don’t fly Avelo. You’ve been warned.

I mean, it’s Spirit. But it was frustrating to have our flight canceled, get bumped to a later flight, and then Spirit was unwilling to check our bag until 4 hours before our flight… tell us we could not sit in the waiting area’s chairs… and really negative experience getting checked in and dropping the bag.

Not having it be changed after we bought the flight tickets from a direct flight getting in at a reasonable time to a connecting flight red eye of 9 hours, so that we would lose our 35 dollars in nonrefundable insurance would've been great! Our country really does need low-cost carrier options, but this type of "service" ain't it. Fortunately, had a little better success with them flying to and from San Juan PR last month at least.

All was good expecting the seats need a bit of cushion. Besides that I can’t complain.

You get what you pay for, and the flights went smoothly. There’s no reclining chairs, no screens, And there isn’t always wifi, but the plane was clean and staff was friendly and the takeoff/landing were smooth.

The only positive is that the flight made it both ways. Getting charged for every little thing after the cost of the ticket itself is comical, considering how the plane and services are as bottom-tier as possible. The self check-in kiosks are useless. It’s nice to think that you can print your boarding pass, tag your checked bag, and then just drop it off. But no, they still make you go through the line once you finish- what’s the point of the self check-in then? Any questions for the staff seem like the biggest inconvenience and were met with condescending responses. This was my first and now last time ever flying with Spirit. After all the extra costs, subpar plane and staff, I see no value. I’d rather drive the 13 hours than give Spirit another dime.

The flight was fine however what started as a reasonable priced ticket could have become an overpriced ticket with additional charge for carry on as well as checked bag $79 per bag per person each way. Additional charge for choosing one’s seat, additional charge for beverage and snack, we were on what was described as a new plane yet there were no audio/visual on the jet. A bare bones service but not at a bare bones price. Will think twice before flying Spirit again. 😕

Flight was delayed a bit, but that was expected (and updated), so really not bad at all for the price. Could’ve used one less email asking me to upgrade my seat; otherwise no significant complaints

I love Spirit. New aircraft, great cabin service, the airfares are low cost which helps me visit my hospitalized daughter anytime I can without paying a fortune.

Flight was 2hours late they had no crew or the pilot.

I paid for streaming wifi and the connection was poor.

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