$43 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 9/6. 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.
1 adult
1 adult, Economy

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Cheap Flights 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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals to Chester

Thu, Oct 16 - Sun, Oct 19
Avelo Airlines Logo
7:49 pm - 9:49 pmCHS-HVN
2h 00mnonstop
Avelo Airlines Logo
4:55 pm - 7:04 pmHVN-CHS
2h 09mnonstop
$88Avelo Airlines
Find Deal
Sat, Aug 2 - Mon, Aug 4
Avelo Airlines Logo
6:10 pm - 7:46 pmRDU-HVN
1h 36mnonstop
Avelo Airlines Logo
7:55 pm - 9:33 pmHVN-RDU
1h 38mnonstop
$89Avelo Airlines
Find Deal
Thu, Aug 21 - Mon, Aug 25
Avelo Airlines Logo
8:15 am - 9:51 amRDU-HVN
1h 36mnonstop
Avelo Airlines Logo
7:55 pm - 9:33 pmHVN-RDU
1h 38mnonstop
$93Avelo Airlines
Find Deal
Fri, Jul 18 - Mon, Jul 21
Avelo Airlines Logo
6:54 pm - 8:59 pmCHS-HVN
2h 05mnonstop
Avelo Airlines Logo
4:05 pm - 6:12 pmHVN-CHS
2h 07mnonstop
$94Avelo Airlines
Find Deal
Fri, Jul 4 - Mon, Jul 7
Avelo Airlines Logo
6:54 pm - 8:59 pmCHS-HVN
2h 05mnonstop
Avelo Airlines Logo
4:05 pm - 6:12 pmHVN-CHS
2h 07mnonstop
$97Avelo Airlines
Find Deal
Fri, Sep 12 - Sun, Sep 14
Avelo Airlines Logo
8:00 am - 9:34 amRDU-HVN
1h 34mnonstop
Avelo Airlines Logo
9:00 pm - 10:38 pmHVN-RDU
1h 38mnonstop
$97Avelo Airlines
Find Deal
Fri, Aug 29 - Mon, Sep 1
Breeze Airways Logo
5:25 pm - 7:09 pmRDU-HVN
1h 44mnonstop
Breeze Airways Logo
9:30 am - 11:23 amHVN-RDU
1h 53mnonstop
$98Breeze Airways
Find Deal
Thu, Jul 10 - Mon, Jul 14
Breeze Airways Logo
11:10 am - 1:33 pmCHS-HVN
2h 23mnonstop
Breeze Airways Logo
2:13 pm - 4:19 pmHVN-CHS
2h 06mnonstop
$102Breeze Airways
Find Deal
Tue, Sep 30 - Tue, Oct 14
Breeze Airways Logo
11:12 am - 1:57 pmMCO-HVN
2h 45mnonstop
Breeze Airways Logo
2:42 pm - 5:46 pmHVN-MCO
3h 04mnonstop
$107Breeze Airways
Find Deal
Sun, Aug 31 - Wed, Sep 3
 Logo
7:28 pm - 10:19 pmPBI-HVN
2h 51mnonstop
 Logo
2:46 pm - 6:09 pmHVN-PBI
3h 23mnonstop
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Good to know - Book Cheap Chester Plane Tickets

Low seasonJanuary
High seasonAugust
Cheapest flight$43
Best time to beat the crowds with an average 26% drop in price.
Most popular time to fly with an average 6% increase in price.
Flight from West Palm Beach to New Haven

FAQs - booking Chester flights

  • How long is the flight to Chester?

    Flights from Fort Lauderdale3h 00m
    Flights from Jacksonville2h 29m
    Flights from Tampa2h 52m
    Flights from Orlando2h 49m
    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 West Palm Beach, at $88 return. The most popular connection is from Orlando to New Haven and KAYAK users have found round-trip deals for as low as $107 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 $75 or less one-way and $91 or less round-trip.
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chester flight deals.

Reviews of the top 4 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 182 reviews
8.2Comfort
8.8Crew
6.6Entertainment
6.8Food
8.4Boarding
Airline reviews

Breeze was good but the sandiego airport had traffic and waiting 1 hour in the plane till take off

10.0 ExcellentAnonymous, Jun 2025SAN - PIT
Read more Breeze Airways reviews

Breeze was good but the sandiego airport had traffic and waiting 1 hour in the plane till take off

The return flight was soooooo much colder than the departure flight to Connecticut! I appreciated the layover because I didn't have to change planes. The staff and the service were the best! Everyone was so professional and accommodating. Having internet was great, but for the movies the flight offers through the app could be updated. THANKS EVERYONE! I fly BREEZE every opportunity I can get.

The flight was comfortable with the usual slight turbulence. Macadamia Nuts would be great snacks to purchase in flight.

This is one of the worst trips that I have ever had. Ending up with an overnight delay. I’m not happy with the fact that they did not provide and set up the arrangement needed for lodging that we had to do it on our own. I also feel there should’ve been Compensation for food.

Had to approach landing twice which caused concern but probably due to weather

This was my first time flying your airline and it was okay. The people were nice but I am not used to all the add ons and no movies or even water. But I knew it was going to be that way. I think I prefer paying for the extras to be more comfortable.

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!

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 missed my flight because I was not informed that I had to check in 45 minutes before my flight and I was not allowed to check in any time after that. I was there at boarding time and their customer service was poor and they told me since I didn't check in 45 minutes prior, I couldn't get my boarding pass. I received an email containing my "e ticket" which I Thought was going to get me boarded.But but they said that was just an Itinerary and it was no good to help me get on the plane. I had already missed one flight earlier that afternoon and had to pay for this flight.And then when I missed it they told me it was gonna cost me another $99 to reschedule my flight

Great experience overall. Early boarding, no delays. Drinks and snacks are not included in price and very expensive. Seats are not very comfortable. Not as much space or padding as other airlines. Good for a quick cheap flight.

My flight got cancelled by Spirit airlines, it was bad experience to me

Crew from Columbus to Atlanta excellent. Flight overall was good. Flight crew from Atlanta to Newark were average probably because they had to deal with overbooked flight and obnoxious people on the flight. Ground crew in terminal needed to do a better job limiting luggage boarding the plane.

Horrible considering I didn’t go and I bought travel insurance and I didn’t receive a refund.

It was absolutely awesome. The crew was welcoming to all, not just the first class. They were full of energy. The in-cabin music was an excellent choice, not boring like most airlines. We were ready for takeoff ahead of time. Pilots were great. Smooth takeoff and landing. The plane was beautiful and nicely cleaned. This was truly a fantastic flight. I fly Delta and American all the time. I was apprehensive about Spirit. I will definitely be looking for Spirit first. Thanks for a great experience.

Didn't like size of seats. Found charges for checked luggage and carry on too high

Great! We boarded on time! Everything went so smoothly! The flight was so smooth

Spirit gets you there; it's no worse than any other aircraft, all things considered. (It's not like everyone else is such a hero). But - holy moses - do they nickel and dime you to absolutely every nickel - I was really expecting to have to pay to use the bathroom. And when the captain comes on with a 5 minute sales pitch about getting "points", that was like something on Bizarro world. Other than that, everyone else was professional and worked hard to get us from point A to point B. I'm not loving all the "self-service" stuff but there it is - just when the machines don't work you don't have anyone to talk to.

Boarding was a breeze, however, two of the flights that I boarded with Spirit did not have Wi-Fi available.

Frontier is terrible. Paid for exit row, not given exit row, refused to refund fee.

2 hour delay due to late plane, wrong size plane causing overbooking, and people getting off and on the plane after boarding was completed.

We had to wait in line over an hour just to check our bags. It's a good thing we were so early to the airport. Only one clerk was working and the line was around the corner and down the hall. No good. I felt bad for her. Not sure how she kept her sanity with all the upset people. Then we get to our gate and there is no seating. Everyone was standing. Then I realize it is not a gate at all, we still have to be shuttled to our airplane. Ugh. Then we were late taking off and missed a window of opportunity before the airport runways were shut down for some reason. (not frontier's fault the runway shut down.) The seats on the airline are crammed and there is no cushion. Never had a tighter seating arrangement while flying. My 6' 4" husband was absolutely miserable the whole time with knees digging in to the seat in front of him. You think you are getting a good deal on a ticket, and then wham! I had to pay 75 dollars for our checked bags and 75 dollars for a carry on. No other airline does that!!! And also, there is a 40 pound weight limit on checked bags... Would have been cheaper flying with another airline, and I would have at least gotten a snack and drink. Was thankful for the tiny cup of water at least.

This was one of the first frontier airline flights this spring that wasn't delayed. It actually left on time. Some of the flight crew did not look happy, they didn't smile when the passengers were boarding or getting off the plane, and the passengers initiated greetings, not the staff. To me this was an odd experience to have with any flight/airline. I had a bad experience booking this flight. The price didn't solidify until late hours into the night. Ever time I purchased the ticket, I either received a denial email or an error because the price has changed, but it was never reflected on the flyfrontier or kayak websites until way after midnight on the date of travel. This caused me anxiety and irritation with the websites. Then I noticed a mishap with my name on my voucher as I went to check in, it was incorrect. When I proceeded to correct it, Frontier had no easy, let alone free, way to remedy it. I couldn't correct my name without a $75 charge, I couldn't cancel my voucher to repurchase it with the correct name without a $100 charge, because it was too close to departure. Then calling frontier was nearly impossible to remedy the situation with a human. It's already difficult to want to choose frontier because of all the upcharges, but you feel kinda trapped into doing so because it's the more affordable airline.

They canceled flight. Hard to believe there was even a plane incoming for us to get on

The worst. We never made our connection and they did absolutely nothing to help us at the airport.

Our flight was cancelled. They could do nothing to help us get another flight that was timely. Because the first leg was cancelled we were unable to get to our connection. We had to book on an entirely different airline for today. So we spent more money, lost a day of vacation and will never fly Frontier again, so the 'we are sorry, here is $100 credit' is a joke since we won't be flying on Frontier.

No way to get boarding pass on my phone. In order to print the bag ticket a boarding pass is needed. Asked the agent to print me one, they said they typically do not due this as its so much work. I showed the email confirmation and I asked how i could do it my self the agent replied he did not know as there was no link. The flight was delayed due to an attendant forgetting to come to work. On the flight no drinks were offered only for purchase meals.

No way to get boarding pass on my phone. In order to print the bag ticket a boarding pass is needed. Asked the agent to print me one, they said they typically do not due this as its so much work. I showed the email confirmation and I asked how i could do it my self the agent replied he did not know as there was no link. On the flight no drinks were offered only for purchase meals.

Since you have to pay for overhead bags then they shouldn't be running out of space and asking individuals who paid to remove stuff from the overhead

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