$70 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 8/25. 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, 0 bags

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Everything you should know

Cheapest round-trip
$127
Typical prices: $249-$141
Frontier
Wed 7/29Wed 8/5
MCO - BDL • Non-stop
Cheapest one-way
$70
Typical prices: $118-$238
Breeze Airways
Tue 8/25
PBI - BDL • 1 stop
Arrival airport
You can't fly directly to Chester. It is served by Hartford (BDL), located 27.9 miles from Chester.
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We hope you love your trip to Chester!
Flight Deals
Useful Info
Flight Deals

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

Wed, Jul 29 - Wed, Aug 5
Frontier Logo
8:48 am - 11:32 am
MCO
-
BDL
2h 44mnonstop
Frontier Logo
11:31 am - 2:29 pm
BDL
-
MCO
2h 58mnonstop
$127Frontier
Fri, Aug 28 - Mon, Aug 31
Multiple Airlines Logo
8:45 am - 11:38 am
MCO
-
BDL
2h 53mnonstop
Multiple Airlines Logo
7:11 pm - 11:41 pm
BDL
-
MCO
4h 30m
1 stop
$136Multiple Airlines
Fri, Aug 28 - Mon, Aug 31
Breeze Airways Logo
2:02 pm - 6:31 pm
MCO
-
BDL
4h 29m
1 stop
Breeze Airways Logo
7:11 pm - 11:41 pm
BDL
-
MCO
4h 30m
1 stop
$137Breeze Airways
Fri, Jul 3 - Tue, Jul 7
Breeze Airways Logo
2:02 pm - 6:31 pm
MCO
-
BDL
4h 29m
1 stop
Breeze Airways Logo
6:00 am - 9:00 am
BDL
-
MCO
3h 00mnonstop
$154Breeze Airways
Thu, Jul 2 - Sun, Jul 5
American Airlines Logo
7:39 am - 9:06 am
DCA
-
BDL
1h 27mnonstop
American Airlines Logo
6:00 am - 7:30 am
BDL
-
DCA
1h 30mnonstop
$258American Airlines
Fri, Jul 3 - Sun, Jul 12
American Airlines Logo
10:40 pm - 12:07 am
DCA
-
BDL
1h 27mnonstop
American Airlines Logo
6:00 am - 7:30 am
BDL
-
DCA
1h 30mnonstop
$259American Airlines
Sat, Jul 25 - Sun, Jul 26
United Airlines Logo
10:25 pm - 11:59 pm
IAD
-
BDL
1h 34mnonstop
United Airlines Logo
6:00 am - 7:26 am
BDL
-
IAD
1h 26mnonstop
$259United Airlines
Fri, Jun 26 - Wed, Jul 8
United Airlines Logo
10:25 pm - 11:59 pm
IAD
-
BDL
1h 34mnonstop
United Airlines Logo
3:02 pm - 4:35 pm
BDL
-
IAD
1h 33mnonstop
$264United Airlines
Fri, Aug 28 - Sat, Sep 5
Delta Logo
5:25 pm - 11:51 pm
IAD
-
BDL
6h 26m
1 stop
Delta Logo
5:06 pm - 11:26 pm
BDL
-
IAD
6h 20m
1 stop
$269Delta
Fri, Aug 28 - Sat, Sep 5
Delta Logo
7:35 pm - 11:51 pm
DCA
-
BDL
4h 16m
1 stop
Delta Logo
5:06 pm - 10:59 pm
BDL
-
DCA
5h 53m
1 stop
$279Delta
Useful Info

Good to know - Book Cheap Chester Plane Tickets

Low seasonJanuary
Cheapest flight$70
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly with an average 2% increase in price.
Flight from West Palm Beach to Hartford

Flights to Chester: the best tips from KAYAK users' own experiences

Insights shared by verified travelers who flew to Chester 
Verified travelerFlew with American Airlines
DFW
-
BDL
Jan 2025
Dallas is huge and has gate changes quite frequently so be sure to set alerts and notifications for your flight.
RoderickFlew with Delta
MSP
-
BDL
Nov 2024
For 7a flight, arrive early! Security lines were very long.
Verified travelerFlew with Breeze Airways
TPA
-
BDL
Mar 2024
Trains connect the airport terminals and you need to take a train from the car rentals to the main terminal

FAQs - booking Chester flights

  • How long is the flight to Chester?

    Flights from Chicago O'Hare Intl Airport2h 02m
    Flights from Orlando Airport2h 44m
    Flights from Tampa2h 40m
    Flights from Washington, D.C. Dulles Intl Airport1h 22m
    Flights from Atlanta2h 16m
  • What is the cheapest flight to Hartford?

    In the last 5 days, the cheapest flight deal to Hartford was found on the route from West Palm Beach, at $127 return. The most popular connection is from Orlando to Hartford and KAYAK users have found round-trip deals for as low as $127 in the last 5 days.

  • Which airlines fly to Hartford?

    Many airlines fly to Hartford, the most common ones being American Airlines, Avelo Airlines, and Southwest. See the amount of flights per week for popular airlines flying to Hartford.

  • How to fly to Chester?

    You cannot fly directly to Chester. KAYAK recommends you fly to Hartford Bradley Intl (BDL) (27.89 miles from Chester). From there you can rent a car or get a taxi.

  • What airports are near Chester?

    The closest airport is Hartford Bradley Intl (BDL) (27.89 mi). Other nearby airports are Albany Intl (ALB) (53.06 mi), Worcester (ORH) (56.38 mi) or Tweed-New Haven (HVN) (70.05 mi). KAYAK recommends you fly to Hartford Bradley Intl.

  • How far is Hartford Bradley Intl Airport from central Hartford?

    There are 12 miles between Hartford city center and Hartford Bradley Intl Airport.

  • What is the name of Hartford’s airport?

    Hartford is served by Hartford Bradley Intl Airport, also commonly referred to as Bradley Intl. The airport code is BDL.

  • 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 Hartford Bradley Intl Airport.
  • Looking for cheap airfare to Chester? 25% of our users found round-trip tickets to Chester for the following prices or less: From Las Vegas $170, from Fort Lauderdale $230, from Miami $329
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chester flight deals.

Reviews of the top 5 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.
8.2
Breeze AirwaysOverall score based on 289 reviews
8.2Comfort
8.7Crew
6.7Entertainment
6.7Food
8.3Boarding
Airline reviews

Flight attendants were wonderful. Seats were comfortable “Nicest” bundle). No screens or meal, but it is a budget airline.

10.0 ExcellentSilvano, May 2026
SFO - CVG
Read more Breeze Airways reviews

Flight attendants were wonderful. Seats were comfortable “Nicest” bundle). No screens or meal, but it is a budget airline.

it is an economy airline so lack of perks expected .. however an efficient board, clean plane, pleasant crew and an early arrival for half the price of full service airline

Very quick and easy process from check in to deboarding and baggage claim. Crew was professional and friendly. Flight was smooth and on time. Very convenient for short flights.

It was easy and very comfortable! The crew was accommodating and cheerful. I enjoyed myself!

I normally have very good experiences with Breeze. The crew is great, pricing is excellent, and the planes are new and usually clean. This time in Huntsville we were delayed, which I understand can happen, however we were moved from one gate to the opposite side of the terminal and then back again... There was a lot of confusion. Also, my seat had a lot of food crumbs still on the floor where I had to stow my bookbag, so that was a bit disappointing. Other than that, all was good. Crew was great as usual!

Our flight was delayed 7 hours. Due to a change in equipment we were downgraded from "Nicest" to "Nicer," even having to pay for a soft drink. Disappointing. To Breeze's credit that issued a $100 flight credit. A refund would have been more appreciated.

Lost my luggage and terrible experience with customer service trying to track it down

10 hour delay with minimal updates. Couldn’t leave terminal and then ended up on redeye with a dirty broken plane. It is literally impossible to reach customer service via gate agent, app, phone, text or email.

I thought that I had pre-purchased carry-on luggage and was surprised when I tried to check in that I did not have it.

Flight departure was 90 min delayed, and the boarding experience was confused, stressful, and generally poor. Additionally, the wifi on the plane was malfunctioning for all but the final 15 min of the flight into ILM.

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

Was fine, delayed and feels like southwest is always late

I don't know why flying out of Sarasota requires two plane changes.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

No gluten free snacks. Seats felt worn or bare bones even though it was a new 737 MAX 8.

One major problem that was very unprofessional and uncalled for. Plane landed and we had to wait 20 minutes to get off the plane since they were waiting for someone to come to the gate to drive the jetway. Southwest couldn't have someone available and waiting for the plane to land? Is there only one person in Hobby airport who knows to drive the jetway? Was he at lunch? In the bar? Uncomfortable and uncalled for!

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

Arrived early, comfortable seats (Comfort+). Mediocre food, poor wifi (intermittent).

Long story short, it was one of the better flight experiences I've had in some time when compared with other airlines.

Flight was great! This flight from Atlanta was even better than when I paid for Comfort from SNA to Atlanta.

Connection flights should be spaced out farther because too close I missed my connection.

Definitely a southern flavor. Cordiality was evident even though no drinks or snacks were served.

On time! There were plenty of airport employees who were able to keep us moving in the right direction. The crew on the plane were professional.

Left /arrived on time. Decent seat space. Like the wifi/plugs and entertainment. Windows and tray table were kinda gross. Attendants didn't start snack service til 40mins before landing. Two rows before us, captain came on to say there's turbulence and recalled staff to seats. So, no drink/snack. Later, attendants didn't stop to see if we had trash nor even look our way. Felt invisible! Almost all pilot announcements were not only unintelligible, but so quiet. We had no idea what she said.

Average seat comfort, a drink and chips were provided, early boarding because we checked a carryon at the gate was nice. Ticket pricing shenanigans, including fees to pick a seat, check a bag, and get food onboard - evidence the industry is reinvigorating last century’s strategies- destroys the experience before one ever arrives at the airport. It’s difficult to recognize any value or sustain loyalty in the end-to-end process making air travel more drudgery than pleasure.

Gate agent was unhelpful for handicapped boarding. Flight attendant seemed untrained.

No service flight that took 5 hrs and a stop at an unscheduled airport. Crew and pilots did their jobs

Packed flight, which makes it tough on crew and boarding staff (and the customers of course). But this was great boarding, clear instructions, etc. Traveling on the weekends are always fraught with danger as you have families and less frequent flyers thus more confusion. But this flight went as planned.

Destroyed my suitcase. Tired of talking about it. Cancelling my unite mileage plus account.

Read the fine print. This was my flight home. I booked my flight for the quickest way home. Had a carry-on and a personal item. Same as my outbound flight. Apparently I needed to pre-pay extra for my carry-on. When I checked in, I was told that I had to check it. I said I’ll pay for it, and was told that this wasn’t an option anymore. They said I still had to pay $50 to check my carry-on. I told them I’ll pay whatever to just carry it in as intended. I was not allowed, so eventually I paid $50 to check my carry-on under a plane that was half full, with overhead compartments that were even less full. My white carry-on suitcase was practically destroyed getting from Idaho falls to Denver to Orange County. The low price air fair was a bait and switch. Got me to the gate, made me pay extra, then didn’t even allow me to pay for a carry on. Not to mention that I paid the $8 for WiFi that didn’t work. All to get my suitcase destroyed. I don’t think I’m going to even keep my Untied mileage plus membership and card. Apparently, membership does not have its privileges for this one.

The flight was delayed, they didn’t even have water for the toilets or for drinks

Even through the flight was delayed due to storms near IAH The flight was great! The crew was so hospitable and professional

I flew from Santa Fe to Denver to catch a flight to London and the transfer of my luggage on arrival at Denver to the London flight worked perfectly. The crew on the ground and on board for the London flight were so friendly and efficient.

Boarded early; and arrived home 40 mins early. After a long flight, it’s nice to be back home early. These flights have no amenities; no snacks. So need to bring your own

Boarded early, left early, arrived 40 mins early! A win win for me!

New plane was lovely. Crew customer service is always lax but expected. Kraft on time and arrived safely.

These airplanes should be illegal. The seats are two tight, it is a safety issue. Wheelchair support was ridiculously slow. We almost missed our flight.

As always, most AA flights that we fly are almost ALWAYS delayed and that too multiple times. Very frustrating

Boarding was smooth and seamless and the flight was without incident.

Very hard to beat a British Airways international flight…the crews are always so amazing! One flight attendant that really stood out was Emma…she was very personable and accommodating with any request we had!!

Our flight was repeatedly delayed for maintenance problems: scheduled for 9.30am, eventually delayed to 7pm! Very very inconvenient! AA should have provided a substitute plane much earlier.. On the other hand, Customer Service crew in Charlotte helped us to reach NY (LGA) by late afternoon. Thank you Patricia!! The actual flight was quick and very comfortable. As always a. excellent, professional crew. [no food on a a short hop).

Take-off delayed an hour because of a missing flight officer, so,arrived in Charlotte lates causing many passengers to miss connections. Otherwise a very good flight, safe and comfortable, with an excellent professional crew.

Little time between flight from Dallas to flight to Gainesville. We chose this one, 43 minutes between, because the price for a connection with at least an hour between, was so much higher. Had to ask passengers on the Dallas flight to please allow us to deplane ahead of them. The economy passengers allowed this. We had to walk very fast to the next gate, 35 gates away. Thankfully all in the same terminal. Getting to the small Gainesville plane was a little confusing as you enter an area that is boarding many small planes at the same time. We stood in the wrong line for about 15 seconds before realizing it was not our Gainesville flight. Since I had boarded at this gate in the past, I knew to check the signs carefully so we weren’t lost. The first class seat experience was wonderful. I really enjoyed the upgrade. We were offered an alcohol drink as soon as we sat down. I got something different but it was a great gesture especially since we really had to hurry to make the flight. We had packed expecting we might miss this connection, but made it. Our luggage didn’t miss the flight. American Airlines delivered our bags to our home the next day. That was very convenient!

The plane was large, not full, but one with 3 seats near each window and 4 in a row in the middle of the plane. There were screens on the backs of the seats for entertainment and information. To use the entertainment one needs ear plugs that physically plug into the screen. My husband had some he let me use as I only had blue tooth type. The stewards gave out some headphones to some, but when my neighbor asked for some, the steward said no. So maybe they ran out? Idk. Bring the old kind of headphones or earbuds if you want entertainment in case this is the type of entertainment offered. We had a very tight connection in Miami. 43 minutes. The other economy passengers allowed us to get ahead of them because I asked if we could since we were near boarding time for our next flight and 35 gates away. They were extremely kind. First class wasn’t going to allow us to pass through. We did make the next flight. Our baggage didn’t, but they were delivered to us the next day and we were prepared with essentials in our carry on packs.

Food is what you expect on a plane. Nothing gluten free. But that is expected. Drinks, apple juice, was fine. Seat, what I expected. Fine.

Everything went as planned. The only issue I had was with the gate C31 attendant. The person could barely speak English and was very difficult to understand.

The flight took off an hour late which made the connection concerning

Everything you need to know for your flight to Chester