$57 Find Cheap Flights to Middletown

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Middletown departing on 9/1. 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
$153
Typical prices: $247-$108
Breeze Airways
Thu 9/3Tue 9/8
MCO - BDL • 1 stop
Cheapest non-stop
$162
Typical prices: $240-$105
Breeze Airways
Wed 8/26Wed 9/2
MCO - BDL • Non-stop
Arrival airport
You can't fly directly to Middletown. It is served by Hartford (BDL), located 26 miles from Middletown.
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We hope you love your trip to Middletown!
Flight Deals
Useful Info
Flight Deals

Cheap Flights to Middletown

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights to Middletown 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 Middletown

Thu, Sep 3 - Tue, Sep 8
Breeze Airways Logo
6:56 pm - 11:11 pm
MCO
-
BDL
4h 15m
1 stop
Breeze Airways Logo
8:10 am - 12:32 pm
BDL
-
MCO
4h 22m
1 stop
$153Breeze Airways
Tue, Sep 22 - Tue, Sep 29
Breeze Airways Logo
12:37 pm - 5:08 pm
PBI
-
BDL
4h 31m
1 stop
Breeze Airways Logo
7:05 am - 11:57 am
BDL
-
PBI
4h 52m
1 stop
$156Breeze Airways
Tue, Jul 28 - Mon, Aug 31
American Airlines Logo
5:27 pm - 11:00 pm
PBI
-
BDL
5h 33m
1 stop
American Airlines Logo
9:13 am - 3:36 pm
BDL
-
PBI
6h 23m
1 stop
$197American Airlines
Sat, Jun 20 - Tue, Jun 23
American Airlines Logo
1:45 pm - 10:02 pm
PBI
-
BDL
8h 17m
2 stops
American Airlines Logo
7:36 am - 12:54 pm
BDL
-
PBI
5h 18m
1 stop
$202American Airlines
Tue, Aug 18 - Tue, Sep 1
Delta Logo
2:17 pm - 8:53 pm
DFW
-
BDL
5h 36m
1 stop
Delta Logo
1:54 pm - 8:50 pm
BDL
-
DFW
7h 56m
1 stop
$267Delta
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
$269Delta
Tue, Sep 8 - Tue, Sep 15
United Airlines Logo
10:25 am - 5:45 pm
DFW
-
BDL
6h 20m
1 stop
United Airlines Logo
6:00 am - 1:09 pm
BDL
-
DFW
8h 09m
2 stops
$272United Airlines
Wed, Sep 16 - Wed, Sep 23
United Airlines Logo
6:45 am - 2:29 pm
DFW
-
BDL
6h 44m
1 stop
United Airlines Logo
6:00 am - 11:40 am
BDL
-
DFW
6h 40m
1 stop
$299United Airlines
Mon, Aug 10 - Sat, Aug 15
Southwest Logo
5:00 am - 12:00 pm
HOU
-
BDL
6h 00m
1 stop
Southwest Logo
11:05 am - 4:35 pm
BDL
-
HOU
6h 30m
1 stop
$312Southwest
Mon, Aug 10 - Sat, Aug 15
Southwest Logo
5:00 am - 12:00 pm
HOU
-
BDL
6h 00m
1 stop
Southwest Logo
5:50 am - 1:55 pm
BDL
-
HOU
9h 05m
2 stops
$317Southwest
Useful Info

Good to know - Book Cheap Middletown Plane Tickets

Low seasonJanuary
Cheapest flight$57
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 Middletown: the best tips from KAYAK users' own experiences

Insights shared by verified travelers who flew to Middletown 
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 Middletown flights

  • How long is the flight to Middletown?

    Flights from Chicago O'Hare Intl Airport2h 02m
    Flights from Orlando Airport2h 40m
    Flights from Tampa2h 41m
    Flights from Washington, D.C. Dulles Intl Airport1h 15m
    Flights from Atlanta2h 15m
  • What is the cheapest flight to Hartford?

    In the last 7 days, the cheapest flight deal to Hartford was found on the route from West Palm Beach, at $153 return. The most popular connection is from Orlando to Hartford and KAYAK users have found round-trip deals for as low as $153 in the last 7 days.

  • Which airlines fly to Hartford?

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

  • How to fly to Middletown?

    You cannot fly directly to Middletown. KAYAK recommends you fly to Hartford Bradley Intl (BDL) (26.01 miles from Middletown). From there you can rent a car or get a taxi.

  • What airports are near Middletown?

    The closest airport is Tweed-New Haven (HVN) (23.71 mi). Other nearby airports are Hartford Bradley Intl (BDL) (26.01 mi) or Islip Long Island (ISP) (58.17 mi). KAYAK recommends you fly to Hartford Bradley Intl.

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

    Hartford Bradley Intl Airport is 12 miles from the center of Hartford.

  • 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 Middletown?

    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 Middletown.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Middletown 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 Middletown?

    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 Middletown 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 Middletown?

    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 Middletown 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 Middletown

  • There is no major airport in Middletown. It is instead served by Hartford Bradley Intl Airport.
  • Looking for cheap airfare to Middletown? 25% of our users found round-trip tickets to Middletown for the following prices or less: From Las Vegas $176, from Fort Lauderdale $220, from Miami $320
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Middletown flight deals.

Reviews of the top 5 airlines flying to Middletown

 
Need help choosing which airline to fly with from the United States to Middletown? 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 288 reviews
8.3Boarding
8.7Crew
8.2Comfort
6.7Food
6.7Entertainment
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.

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.

I'm glad it wasn't only 75% full because I could get a good seat

if I was good. Not happy that I have to pay extra money to get the seat I need for lake room, but I guess that’s a sign of the times.

Seats were very comfortable. They tilted back. Drinks and snacks were free and served 3 times. Attendants were awesome.

Plane was clean and comfortable. Flight attendants and gate staff were professional, friendly and efficient. Boarding and deplaning were orderly and efficient. All in all, the typical excellent Southwest experience.

Truly terrible. Will never willingly fly southwest again. Seats are worse than before they switched to assigned seating. One flight attendant was the opposite of helpful (rude, unhelpful, dismissive, and as my stranger seatmate said unprompted: a total prick). This caused me, 15 minutes into the flight, to book an alternate return flight home on a competing airline (first class 1.2k purchase instead of my existing planned flight) just so I would not have to ever be on that aircraft, with that terrible service person, with those horrific seats ever again.

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

Clean planes and not take my comfort class seat away.

Weather caused a long delay, but the efficiency and updates from the pilot were helpful. We were able to make our connection fortunately.

Planes were clean, no water or snacks on either flight.

Free & relatively fast Wi-Fi. Would've liked a wider drink selection.

I continue to be satisfied with Delta’s excellent service out of LGA. The digit id works well and gets me through security in no time. Whenever possible, I choose Delta.

Was revoked with Jet Blue due to delay from Kenya Air

Enjoyed it very much. Especially liked the free WiFi that Delta offers.

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.

It was a short flight so I was expecting too much

Horrifying Almost 2 million miles. Bring your own food and drink. One coffee or drink every three hours. Have to order meals on app more than 24 hours ahead Tiny and dirty bathrooms

Flight was delayed but more than 90 minutes. This caused me to miss my available windows for pick-up by a friend. I had to pay $125 for an uber back home from the airport which was an added expense that I had not budgeted for my trip. Staff was friendly.

Seat pitch is horrible especially on the 15 hour flight. Gate crew at SFO was Outstanding. The flight crew was also great.

Had a one hour delay due to mechanical issue. I didn’t think I’d be able to make my connecting flight, but they waited for me and greeted me when I arrived to help things run smooth.

6 1/2 hours from Tampa to SFO on a Boeing 737. Cramped. No Service. No real food. One pass for coffee at the beginning and a second pass THREE hours later. And check-in in Tampa was nasty even by United standards. And I am at almost TWO million miles on United. It's a non-stop. But terrible service.

The flight from Dallas to Tokyo was not on Japan Airlines. It was on American Airlines. Very disappointed that we did not fly on Japan Airlines. Will not be using you liars again. I’ll just book direct from the airline next time. Wish you could make this right and has us fly on Japan Air when heading back home to the US.

The Mario was so helpful and provided amazing customer service however l have being waiting for a callback for almost a week now and have not heard anything further after l informed them l wanted to change my date of traveling because of my hospital appointment even send them proof and l was unable to use manag your booking on their website is a bit frustrating and l would appreciate an update on My request as soon as possible. And have called them times without numbers no response

They made nearly everyone check their bag because the overhead bins are way too small. Extremely inconvenient

Was put into a seat right behind the toilet that had no entertainment possible but did have plenty of leg room over noisy part of plane.

Movies on my phone are great. It would be nice to have a gluten free snack option.

It was what i expected. I like the movies you can access from your phone. It would be nice if there was a gluten free snack offered. But I did bring my own snack knowing there would not be a gluten free option

The flight was peaceful, just s slight turbulence, pilots and crews were all nice and made a great job! Arrived safely in the Philippines. Thank you ya’ll!

Ontario airport boarding was very easy to park and access, is clean and TSA took 10 minutes total. Check-in was a breeze and cruise was very nice.

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.

Everything you need to know for your flight to Middletown