$96 Find Cheap Flights from New York to Caribbean - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from New York to Caribbean departing on 9/12. 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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Cheap Flights from New York to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$376
Santo Domingo
Santo Domingononstop$239
Montego Bay
Montego Bay1 stop$381
Oranjestad
Oranjestad1 stop$361
Nassau
Nassaunonstop$302
Kingston
Kingston1 stop$386
Simpson Bay
Simpson Bay1 stop$367
Providenciales
Providencialesnonstop$371
Port of Spain
Port of Spainnonstop$345
Bridgetown
Bridgetownnonstop$442
George Town
George Town1 stop$333
Willemstad
Willemstad2 stops$332
Castries
Castries1 stop$541
Aguadilla
Aguadilla1 stop$336
Puerto Plata
Puerto Platanonstop$490
St. John's
St. John'snonstop$446
Punta Cana
Punta Cana1 stop$376
Santo Domingo
Santo Domingononstop$239
Montego Bay
Montego Bay1 stop$381
Oranjestad
Oranjestad1 stop$361
Nassau
Nassaunonstop$302
Kingston
Kingston1 stop$386
Simpson Bay
Simpson Bay1 stop$367
Providenciales
Providencialesnonstop$371
Port of Spain
Port of Spainnonstop$345
Bridgetown
Bridgetownnonstop$442
George Town
George Town1 stop$333
Willemstad
Willemstad2 stops$332
Castries
Castries1 stop$541
Aguadilla
Aguadilla1 stop$336
Puerto Plata
Puerto Platanonstop$490
St. John's
St. John'snonstop$446

Book Cheap New York to Caribbean Plane Tickets

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

Sun, Aug 30 - Tue, Sep 1
United Airlines Logo
8:00 am - 11:57 am
EWR
-
SJU
3h 57mnonstop
United Airlines Logo
1:00 am - 5:04 am
SJU
-
EWR
4h 04mnonstop
$267United Airlines
Tue, Aug 11 - Tue, Aug 18
American Airlines Logo
5:00 pm - 11:59 pm
JFK
-
SJU
6h 59m
1 stop
American Airlines Logo
7:24 pm - 1:28 pm
SJU
-
JFK
18h 04m
1 stop
$276American Airlines
Wed, Aug 26 - Wed, Sep 2
Delta Logo
12:40 pm - 4:33 pm
JFK
-
SJU
3h 53mnonstop
Delta Logo
5:50 pm - 10:04 pm
SJU
-
JFK
4h 14mnonstop
$277Delta
Sat, Aug 8 - Wed, Aug 12
JetBlue Logo
7:20 pm - 11:29 pm
JFK
-
SJU
4h 09mnonstop
JetBlue Logo
9:10 pm - 1:07 am
SJU
-
JFK
3h 57mnonstop
$278JetBlue
Mon, Jul 20 - Tue, Aug 4
JetBlue Logo
8:00 pm - 12:13 am
JFK
-
SJU
4h 13mnonstop
JetBlue Logo
5:01 am - 8:54 am
SJU
-
JFK
3h 53mnonstop
$282JetBlue
Sat, Aug 8 - Wed, Aug 12
Delta Logo
7:28 pm - 11:52 pm
JFK
-
SJU
4h 24mnonstop
Delta Logo
7:30 am - 11:25 am
SJU
-
JFK
3h 55mnonstop
$287Delta
Wed, Sep 2 - Tue, Sep 8
Frontier Logo
8:29 pm - 8:11 am
LGA
-
SJU
11h 42m
1 stop
Frontier Logo
8:57 pm - 3:59 pm
SJU
-
LGA
19h 02m
1 stop
$288Frontier
Tue, Sep 1 - Wed, Sep 9
Frontier Logo
8:29 pm - 1:16 pm
LGA
-
SJU
16h 47m
1 stop
Frontier Logo
3:00 am - 3:59 pm
SJU
-
LGA
12h 59m
1 stop
$300Frontier
Thu, Sep 10 - Sat, Sep 12
Arajet Logo
12:00 pm - 4:19 pm
EWR
-
PUJ
4h 19mnonstop
Arajet Logo
7:10 pm - 11:30 pm
PUJ
-
EWR
4h 20mnonstop
$396Arajet
Sun, Oct 18 - Sat, Oct 24
Arajet Logo
12:00 pm - 4:19 pm
EWR
-
PUJ
4h 19mnonstop
Arajet Logo
7:10 pm - 11:30 pm
PUJ
-
EWR
4h 20mnonstop
$398Arajet
Booking Insights

KAYAK's insights & trends for New York to Caribbean flights

Get data-powered insights and trends into flights from New York to Caribbean to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest New York to Caribbean flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Caribbean from New York found in the last 5 days was to Nassau, at $110 round-trip. The most popular route is from New York John F Kennedy Intl Airport (JFK) to Santiago de los Caballeros (STI), and the cheapest round-trip airline ticket found on this route in the last 5 days was $397.

What is the cheapest time of day to fly to Caribbean?

The average price for all round-trip flights from New York to Caribbean depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Caribbean is generally in the afternoon, when round-trip flights cost $295 on average. Morning departures are around 3% cheaper than evening flights, on average. The most expensive time of day to fly to Caribbean is generally in the evening, which is peak travel time and where the average cost of a ticket is $353.

Can I save money by flying with a layover from New York to Caribbean?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $607, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from New York to Caribbean?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from New York to Caribbean, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from New York to Caribbean is October, when tickets cost $384 (return) on average. On the other hand, the most expensive months are December and July, when the average cost of round-trip tickets is $591 and $556 respectively.

What’s the cheapest day of the week to fly from New York to Caribbean?

The average price of all round-trip flights from New York to Caribbean clicked on KAYAK for each day over the last 12 months.

For New York to Caribbean, Monday is the cheapest day to fly on average and Thursday is the most expensive. Flying from Caribbean back to New York, the best deals are generally found on Friday, with Sunday being the most expensive.

How far in advance should I book a flight from New York to Caribbean?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from New York to Caribbean, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from New York to Caribbean, you should book around 2 weeks before departure, which saves you about 11% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 26 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$96
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly with an average 15% increase in price.
Flight from Newark Liberty Airport to Oranjestad

Flights from New York to Caribbean: the best tips from KAYAK users

Insights shared by verified travelers who flew the route from New York to Caribbean 
Maria AlejandraFlew with Frontier
JFK
-
SJU
Aug 2024
Buy some food and beverage for that 4 hours trip. And download some movies in Netflix
Verified travelerFlew with United Airlines
EWR
-
SDQ
Apr 2024
Early check in online, get on time for the flight

FAQs - booking Caribbean flights

  • Which airport in New York has lounges?

    If you are flying to the Caribbean on a long-haul flight, consider flying from JFK, as the airport has lounges with various amenities to relax before your flight. JFK has airline lounges, including Delta Sky Club, British Airways Lounge, Emirates Lounge, and Lufthansa Senator Lounge, and pay-per-use lounges, including American Airlines Admirals Club, Alaska Lounge, and Air France Lounge. Enjoy complimentary food and beverages, showers, kid's areas, and premium services, including private suites and spa treatments before your flight departure.

  • Which Caribbean airport should I fly to from New York to visit Jamaica?

    Jamaica's primary airport is Sangster International Airport (MBJ) in Montego Bay. The airport has several direct flights to and from major cities, including New York. The airport connects to various parts of Jamaica through public transportation options, including public buses, shuttle buses, and route taxis, making visiting your preferred destination within Jamaica easy.

  • Which Caribbean airport is ideal for business travelers?

    When flying to the Caribbean for business purposes, consider flying into Luis SJU. The airport provides modern business facilities, including conference rooms, meeting rooms, and workstations with charging stations. The airport is also in San Juan, a significant business and financial hub in the Caribbean, and is close to the city center and convenient for accessing business-related facilities.

  • Which Caribbean airport is well-connected to bus and ferry systems?

    Luis Muñoz Marín International Airport (SJU) is connected to various parts of San Juan and other towns on the island by bus. After your flight from New York, you can take a bus from the airport's ground transportation area to your desired destination within the island. You can also use ferries to connect to nearby islands, including Culebra and Vieques from Puerto Rico.

  • How does KAYAK find such low prices on flights from New York to Caribbean?

    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 from New York to Caribbean.

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

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

  • What is the Hacker Fare option on flights from New York to Caribbean?

    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 from New York to Caribbean 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 from New York to Caribbean?

    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 from New York to Caribbean 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 Caribbean

  • New York City has three primary airports, New York Airport (JFK), LaGuardia (LGA), and Newark Liberty Airport (EWR), located in Newark but serves the New York metropolitan area. The main airport in the city, however, is JFK, with extensive flight options and connectivity to Caribbean destinations.
  • If you are flying into the Caribbean for the beaches, consider flying into Princess Juliana International Airport (SXM) in St. Maarten, as the airport is close to Maho Beach and Orient Bay Beach. The airport is also on a dual-nationality island, making it suitable for experiencing Netherlands and French cultures.
  • Luis Muñoz Marín International Airport (SJU) is a major hub for several airlines, including Air Sunshine, Seaborne Airlines, Cape Air, and Wiggins Airways, and a focus city for JetBlue and Silver Airways. Flying into SJU from New York offers numerous flight options and is ideal for comparing flight fares suited to your budget.
  • When flying from New York to the Caribbean, SJU in San Juan has the most significant number of direct routes from New York by Delta Air Lines, Spirit Airlines, United Airlines, and JetBlue and is well-connected to other Caribbean destinations with a range of flight options.
  • If you have special needs, consider flying to Europe from JFK, as the airport provides wheelchair assistance services, accessible restrooms and parking, visual and audible information, telecommunication devices for people who are hard of hearing, special assistance lounges, and service animal relief areas. It is equipped with elevators and escalators to access different levels of the airport.

Reviews of the top 5 airlines serving from New York to Caribbean

 
Need help choosing which airline to fly with from New York to Caribbean? 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.
7.8
DeltaOverall score based on 8420 reviews
8.1Boarding
8.5Crew
7.8Entertainment
7.2Food
7.8Comfort
Airline reviews

Third flight in two months where the crew was not there. Comfort seating does not guarantee overhead bin space. Passengers with children are allowed on the plane first - if you are flying to and from Orlando, this means half the plane has boarded before you get on. And somehow all the bin space is taken up. 3 out of 5 flights have had issues with equipment or procedure. Some of these instances caused the flight to be delayed because of a "nuisance" light. One time it was a bag that had been brought on board but did not belong to anyone so we had to return to the gate. Last night we were told the "AC" on the plane doesn't work well and we're 10th for take off- because the crew was late - and that it will get cool when we're in the air. Not sure if this is usual, but I didn't think flight crew could jump seat in first class. Movie and TV selection has not been refreshed for several months- flying one to two round trips each month easily exhausts the list of content.

2.0 MediocreHeather, Jun 2026
LGA - MCO
Read more Delta reviews

Third flight in two months where the crew was not there. Comfort seating does not guarantee overhead bin space. Passengers with children are allowed on the plane first - if you are flying to and from Orlando, this means half the plane has boarded before you get on. And somehow all the bin space is taken up. 3 out of 5 flights have had issues with equipment or procedure. Some of these instances caused the flight to be delayed because of a "nuisance" light. One time it was a bag that had been brought on board but did not belong to anyone so we had to return to the gate. Last night we were told the "AC" on the plane doesn't work well and we're 10th for take off- because the crew was late - and that it will get cool when we're in the air. Not sure if this is usual, but I didn't think flight crew could jump seat in first class. Movie and TV selection has not been refreshed for several months- flying one to two round trips each month easily exhausts the list of content.

Great experience nice pilot very soft and easy landing and take off

Flight was delayed before take off and at landing. Baggage took 20 minutes. Flight crew would not serve full soft drink and had to ask multiple times before receiving water.

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.

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

WiFi didn’t work. Flight delayed 3 hours Crew members were illiterate Seat lean back did not work.

Transparency from pilots, quick boarding and exiting the plane, staff greeted to each and everyone,

WiFi didn’t work most of the time. The usb chargers would work only occasionally for 5 mins and wouldn’t charge after that. Had to keep trying repeatedly at each of the seats in the row.

The crew bent over backwards to thank us for flying and make us comfortable. The food service was quick and efficient. The Captain communicated and said goodbye and thank you as we departed. They really stood out!

Crew was amazing, takeoff wonderful. The bathroom was disgusting from before takeoff the odor made the flight uncomfortable as you could smell the bathroom from the center of the plane where we were sitting. Smelled like raw sewage. My daughter was throwing up as we landed due to the smell and horrible turbulence as we approached Newark.

I'm a United 1K member and have ben for 10 years. The gate agent had no control over the boarding process and had us passengers queued for hours as delays were announced. On the plane, the overhead air nozzle was broken so col over was powering through on me and the passenger next to me. Not a great experience for a million miler on United. Feel free to contact me. Josh Smigel - DM426089

Everything was the best it could be. Crew found me with pre- ordered food. Excellent experience!

Improve the food offerings and cabin seating. My wife would prefer to fly another airline, even with a connection for a more comfortable trip. A 737-8 should not be scheduled for a 6 hour segment, which turned into 7.5 hours due to the origin ground delay.

Check in was chaotic with only one counter for business class and first class. The luggage conveyor belt at JFK airport was broken so the flight departure was delayed which made the flight stressful as I had a tight connection. Although the captain said they could make up the delay, they didn’t do so.

As I wrote earlier, poor planning and/or communication. At least twice, we were told that we would be boarding in less than ten minutes, only to have the flight again delayed at least another hour.

Cree was organized and pleasant. Plane had good seating but as it’s a shuttle toilets hadn’t been thoroughly cleaned (eg. bins too full)

All good flight was 35 minutes early when arriving in Edinburgh

Flight left on time, arrived early, pleasant staff provided water, coffee, etc. access to bathrooms was reasonable and were well maintained. blankets were available, lots of entertainment options. LUGGAGE SERVICE WAS GREAT. I got my one checked bag quickly and was able to make a bus connection for a 2 hour bus ride saving me from waiting another 1.5 hours.

I had a good time. However, I paid for the wifi and it was in and out the whole flight.

Crew were professional and kind. The flight was smooth. But... The internet, which we paid 35 dollars for, did not work for most of the flight. This made providing media for our child an uncomfortable hassle.

Overall fine. Seemed like one of the older model planes? Crew was mostly very kind, though some of the female attendants were a rather abrupt during the food service.

Leave on time. We waited on the plane for hour hours and it was hot and smelly

The flight attendant on my side of business class seemed like a novice and did not provide good service. Otherwise the flight was good and the entertainment system was very good. No free WiFi.

Flying in the United States with the major airlines has become so underwhelming. A 2-3hr flight in most other parts of the world with the major carriers of the area comes with newer, CLEANER aircraft and significantly better in flight service in terms of both staff attitude and a actual meal service.

I am writing to share detailed feedback regarding my recent journey with American Airlines on the New York (JFK) to New Delhi (DEL) sector, which was ultimately diverted to Jaipur (JAI) due to weather conditions. At the outset, I would like to acknowledge that this was a full long-haul flight of approximately 14–15 hours, and while the journey fulfilled its primary transport objective, several aspects of the experience warrant both recognition and constructive feedback. 1. Cabin Crew Conduct and Service Consistency While the majority of the cabin crew maintained a polite and professional demeanor, one flight attendant’s conduct was notably inconsistent with expected service standards. The tone was often directive and lacked the warmth and guest-centric engagement typically associated with long-haul service. This created a perceptible imbalance in the cabin experience. Although other crew members acknowledged and apologized for the behavior, it highlighted a gap in service standardization and supervisory oversight. 2. Inflight Experience (IFE & Comfort) The inflight entertainment system was unreliable, with content failing to load consistently throughout the journey. Seating comfort in economy class was below expectations when compared with other international long-haul carriers. Cabin environment management at times felt unsettled, with noticeable noise and movement in the aisles. 3. Disruption Handling and Communication (DEL Diversion to JAI) The diversion to Jaipur due to weather was understandably beyond the airline’s control. However, the handling of post-diversion communication and guest management was an area of concern: Information during and after the diversion was fragmented and lacked clarity Limited guidance was provided upon disembarkation regarding next steps (transport, accommodation, onward travel) Ground coordination appeared inconsistent, with hotel partners and passengers receiving incomplete or delayed updates Communication the following morning remained unclear, including last-minute changes to transfer timings This resulted in avoidable uncertainty during a critical disruption phase. 4. Positive Acknowledgment – Ground Recovery Arrangements It is important to recognize that despite the initial communication gaps, the overall recovery framework was eventually well executed: Hotel accommodation was arranged efficiently Meal vouchers were provided appropriately Transfers between airport and hotel were organized in a structured manner Given the sudden and large-scale disruption, these arrangements were commendable and reflect the airline’s ability to operationally recover once systems were in place. 5. Recommendations for Improvement In the interest of strengthening the overall customer experience, I would respectfully propose the following: Service Delivery Reinforce consistent cabin crew service standards, particularly for long-haul sectors Enhance supervisory presence to address outlier behaviors in real time Inflight Product Improve reliability of inflight entertainment systems Reassess economy seating comfort for ultra-long-haul routes Disruption Management Establish a more visible “Care & Coordination Team” during irregular operations Ensure clear, centralized communication (single source of truth) for passengers and ground partners Provide structured briefing points to hotel and transport vendors to avoid information gaps Introduce proactive guest engagement (clear next steps, timelines, reassurance) Closing Reflection: While the journey was impacted by both controllable and uncontrollable factors, the overall experience would have been significantly enhanced through greater consistency in service delivery and more structured communication during disruption. I appreciate the efforts made by the broader team in arranging accommodation and onward logistics under challenging circumstances. With improved coordination and alignment, the experience can be elevated to match the expectations of a global long-haul carrier. Thank you for your attention to this feedback. I trust it will be received constructively and contribute to ongoing service improvement. Warm regards, Soosnata Chowdhury Convert effective for airlines) Or tailor tone

Wifi was spotty. Tray table was very dirty when I sat down.

Flight was extremely hot and they made us check our bags when the space was nowhere near full

Same plane as RDU to LGA — internet not working. Pilot issue of some sort at end of prior flight - I was on same plane for my connection. Late/delayed —

For an international flight the seats were smaller than most flight I have been on in economy. I don’t know the size of the seats or perhaps it was the size of the seat dividers that made the seats feel smaller and little amount of space to even turn your body if you needed to

First the flt was delayed over 2 hrs bc of plane mechanics that should have been handled better! No text or email was sent so only found out at the airport so there we sat for 5 hours! THATS RIDICULOUS! The gate area was filthy! No agents showed up till hr before so no additional info was given-waited online for 15 mins while the gate agent chatted and got together then given last seat in back of plane!! No priority for senior or anything-took attendants over 2hrs to serve drinks and snack-WHY are they not served together? By time snack came needed another drink! Worst service in my life!

All the TV screens in my rows was non functional . The map shown for an international route was antiqued..

Boarding process was terrible. No assigned seat until the gate, then a long line to get seat assignment.

The space between seat rows seemed to be larger than other airlines. I didn’t check their food or entertainment since I slept most of the way. They do seem to have a lot of options for purchase though.

Kayak sucked. You gave me a confirmation number that was not useable by the jet blue system. Nor did you send any check in emails. I’ll not be using your site again. Nice work.

Automated scanning was slow and somewhat haphazard. Too many people were unfamiliar with the tech and were forced to learn on the fly. The hands off approach of the gate staff made it more uncomfortable. This needs work. Overall the flight and cabin crew were excellent.

Crew were fantastic and so catering and wonderful! Full score for the entire crew!

Terrible. They canceled our early morning flight after midnight on the day of and had no available flights to rebook my family on for the next 72 hours. Yet they still had other flights that were not cancelled from JFK so it couldn’t be based on the weather. It felt like they canceled the flight based on it not being profitable enough for them. I am not interested in traveling with the again. The absolute worse customer service and lack of accountability.

First time flying with JetBlue and never again. I went to the counter to request meet and assist because I'm 74 and my wife is 79. I walk with a cane and my wife is handicapped and has her own wheel chair. I told the agent that my wife and luggage was at the entrance door. The ticketing agent said to me that they don't offer meet and assist. I need to bring them our luggage and then go back and get my wife in order to get my boarding pass. As I went back to get my luggage a Southwest agent along with a TSA agent recognized the situation and came over and took my wife and luggage to the JetBlue ticketing counter alongside the line and told the JetBlue agent to issue to take our luggage as soon as they could.

Flight was fine, price was good but food onboard was abysmal. I was on there for breakfast and lunch and dinner 845am EST to 845pm GMT and all I got was a yoghurt parfait, fruit and a piece of cake. Later snacks included an ice-cream brownie and a pizza twist. I was hungry by the time I landed and the airport amenities were closed. Not happy.

There weren't enough employees at check in took awhile to get bags checked. There wasn't a wheel chair for me, I was sent to someone who turns out to work for a different airline, if My flight hadn't been delayed I probably would have missed my flight as it was, by the time I arrived at my gate, they started boarding in about 15 minutes. I don't know who took me to my gate, definitely was not the normal people who take passengers to the gate. I'm guessing she may have been in a management position. I wish I knew her name, she went beyond to help me. With that said everyone was kind, and were doing the best they could. So, I choose to say it was an Adventure, stressful start, but good. In the end went well. The situation was not only difficult for passengers but the employee's.

The staff at the check in counter was so rude. Made you feel Incompetent

Frontier scheduled a 40 minute connection in DEN. What they failed to mention was that they “close the doors” 20 mins prior to departure, which means you only have 20 mins. Not enough time. Possibly against DOT regulations. Filing complaint.

Flight was scheduled at 9:40pm. Got delayed to 10 am, the next day. crazy

The bag check, flight check-in, and onboard experience convinced my wife and me that we will actively go out of our way to avoid flying Frontier Airlines in the future. At bag check, we were informed that check-in could only be completed via the Frontier mobile app. Unfortunately, the app was extremely frustrating—sending us through repetitive, confusing loops that repeatedly forced us to decline add-on services with nearly every click. While most airline apps upsell, this one felt intentionally exhausting. As the process dragged on, we became genuinely concerned that my phone battery would die before check-in could be completed. We approached the bag check staff—who were standing together talking—and explained both our frustration and our predicament. They laughed. Later, my wife described the interaction as “gaslighting,” which felt accurate. We were then informed it would cost $25 per person simply to have our boarding passes printed. From that point forward, the tone of the experience was consistently hostile. The bag check employees were condescending and combative, behaving more like bullies than customer service staff. Unfortunately, that same attitude continued onboard. One flight attendant argued with me when I attempted to stow my backpack in the overhead bin. I explained that we had each paid $75 to check our bags specifically so we would not need to use carry-on space and could have adequate legroom. She demanded to see my ticket, pointed out that it said “no carry-on”—which I acknowledged—and I reiterated that this was precisely why we paid to check our bags. Her response was, “I don’t make the rules.” She then walked away, but not before asking if I “truly wanted to fly back to Chicago today?”—an unnecessary and unmistakable threat. It is also worth noting that despite booking our tickets together in the same transaction, we were not seated together. Upon our return to Chicago—where we could once again sit together—we compared onboard experiences. We both remarked on how unhappy the flight attendants appeared and how each of us was separately asked whether we would like to purchase a beverage. We declined. At no point was water mentioned as an option, leaving us with the clear impression that even water came at a cost—or that complimentary water, if available at all, was deliberately left unmentioned. Overall, the experience was shocking and deeply disappointing, but it was also a profound learning experience—one we will not forget and will not repeat. -Steve

Plane was hot and miserable and the crew was rude!

12 hour delay required getting on and off plane 3 times - would have at least liked to have been offered a snack or drink

They didn’t offer a water, even after I asked

They switched our terminal 3 times and we were delayed for four plus hours!!!

It was an early flight and most people napped/slept and the crew let us which was nice.

Everything you need to know for your flight to Caribbean

Cabin class types available on flights to New York

Cabin classes available on flights to New York. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.