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Cheap Flights from Omaha to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Punta Cana
Punta Cana1 stop$535
Santo Domingo
Santo Domingo1 stop$680
Montego Bay
Montego Bay1 stop$454
Oranjestad
Oranjestad1 stop$596
Nassau
Nassau1 stop$452
Providenciales
Providenciales1 stop$513
Bridgetown
Bridgetown1 stop$811
George Town
George Town1 stop$510
Willemstad
Willemstad1 stop$700
Puerto Plata
Puerto Plata2 stops$871
St. John's
St. John's2 stops$849
Punta Cana
Punta Cana1 stop$535
Santo Domingo
Santo Domingo1 stop$680
Montego Bay
Montego Bay1 stop$454
Oranjestad
Oranjestad1 stop$596
Nassau
Nassau1 stop$452
Providenciales
Providenciales1 stop$513
Bridgetown
Bridgetown1 stop$811
George Town
George Town1 stop$510
Willemstad
Willemstad1 stop$700
Puerto Plata
Puerto Plata2 stops$871
St. John's
St. John's2 stops$849
Booking Insights

KAYAK's insights & trends for Omaha to Caribbean Islands flights

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

Can I save money by flying with a layover from Omaha to Caribbean Islands?

No, with an average price for the route of $397, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Omaha to Caribbean Islands?

The cheapest month for flights from Omaha to Caribbean Islands is April, when tickets cost $558 (return) on average. On the other hand, the most expensive months are November and June, when the average cost of round-trip tickets is $775 and $761 respectively.

How far in advance should I book a flight from Omaha to Caribbean Islands?

To get a below average price on the flight from Omaha to Caribbean Islands, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 6 weeks before departure.

Good to know

Low season

August
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly and prices are also 19% lower on average.

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from Omaha to Caribbean Islands?

    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 Omaha to Caribbean Islands.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Omaha to Caribbean Islands 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 Omaha to Caribbean Islands?

    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 Omaha to Caribbean Islands 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 Omaha to Caribbean Islands?

    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 Omaha to Caribbean Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 5 airlines serving from Omaha to Caribbean Islands

 
Need help choosing which airline to fly with from Omaha to Caribbean Islands? 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.
8.0
SouthwestOverall score based on 4214 reviews
8.0Comfort
8.6Crew
7.5Entertainment
8.1Boarding
7.0Food
Airline reviews

When I made my reservation it would have been nice if kayak would have included my luggage. Unaware that I had to pay $45 each way. Should have asked at reservation time if luggage was being checked

8.0 ExcellentJeremy, Nov 2026
Read more Southwest reviews

When I made my reservation it would have been nice if kayak would have included my luggage. Unaware that I had to pay $45 each way. Should have asked at reservation time if luggage was being checked

Crew was a little surly. But plane left on time and arrived early. All one can ask for. New 737 Max was nice.

Flight was delayed about 50 minutes and completely full. they did the usual demand for people to check carry-ons. they called all groups to board very fast only to stand in the gangway after having boarding passes scanned. Why don't airlines board from the back to front - since they now have assigned seats? our stewardess got drink orders confused, so she just called out "cranberry". etc.,.. I wish they wouldn't serve pretzels snacks with a powdered coating, as it sticks to your hands and they don't have wet wipes. don't want to lick my fingers after hanging out in the terminal for over an hour.

Delayed over 3 hours, extremely rough landing on all four flights. Would not recommend

Boarding, crew and inflight entertainment was great. Could have better food options for a long flight. Paid money and got a seat with extra leg space but was asked to keep my carry on under the seat in front of me which defeats the purpose of buying a extra space seat.

On time departure and arrival. Had to be the oldest plane in the SWA fleet but it got me where I needed to be.

Flight was delayed out of BWI unexpectedly / without a reason given but otherwise ok.

I got a bit sick on the flight, and was so grateful when the male flight attendant explained to me they keep the back row open for cases like mine. He took such great care of me! I was incredibly grateful.

The new seating arrangement is so over priced for what you get.

Southwest never has accurate baggage claim policy information at Denver. They list one claim on the screens and invariably baggage is eventually found on another claim with zero help from staff.

Great overall experience and use of the Delta One lounge was amazing!

I used by Skymiles to upgrade to First so that I could comfortably work using my laptop. But WiFi was intermittent and unavailable for long periods. I feel like I wasted 70,000 miles :(

Great as one can be for a one connection 6 hour flight

Packed flight and not sure why dinner service would start at midnight while passengers we’re trying to sleep

The gate attendant was not clear w message on flight delays.

Chairs don’t recline and the ones that do recline, barely do recline. It was most uncomfortable flight i ever been on.

Good but not on par when compared with foreign flag carriers.

Very nice the whole crew was amazing and very professional. I had an offer for a drink it was handled great and amazing crew and nice flight.

The number of interim flight delays has been higher than I can remember in my history of travel making any connection a mystery as to whether you will actually make it.

Of course, the Gate change was last minute and they were boarding g when we finally got to the change of terminal as well.

1 person checking us as we boarded, left gate on time, 12.30 we are told we were held for 15 mins as other flights were waiting to take off, captain due to rain … they were having a longer gap between take offs , 3pm we took off , they went land route via New Orleans in to Florida landed at 5.45pm offered coffee and a biscuit

Service was slow Flight was very loud at back of plane

There was no internet on the flight. As an executive flying during prime business hours, having internet is critical for a smooth experience. This impacted productivity and time that will need to be spent later to do the work I could have done on flight.

Terrible boarding - 4 flights boarded from the same gate. Chaos there; long ramps to the plane.

Flight delay in lax which delayed our connecting flight to Copenhagen. Was placed on standby the following day and got delayed again at Scandinavian air. Bad bad counter service at ar Canada in Toronto by the name of Camilla who said that she was doing us a courtesy for even finding a earlier flight for us after we the customer are the ones being inconvenient by the cancellation of our flight. Btw, we are going on a tour. Air Canada is the worse

Seats needs to be wirer and food is very poor

It was good overall except from Omaha to Denver when flight a was a repeatedly delayed apparently due to some issue at Denver. Communications could have been handled better. I had to board then deboard with luggage and board again

There were issues with the first segment but what really bothered me overall is that you rebooked me and put me in a seat away from my wife and then put her in another booking or boarding group. I don't like having to monitor every little thing you guys do in order to get what I paid for in the first place.

The staff was phenomenal. I can’t think of anything that could be better. Will be flying with UA again

I had very little time to change planes originally in Denver after my flight from Omaha. I had an hour and a half layover in Denver originally and my flight leaving Omaha was delayed an hour because they had to change a tire which I can understand. When I reached Denver my other flight was late, fortunately, but I still had only 10 minutes to run about a mile through the airport to get to my flight. Again, fortunately I am a healthy 71-year-old and was able to accomplish this feat. However, the stress was more than necessary to bear.

The boarding agent and checked bag agent were both rude. It only takes a second to be kind. However, the flight crew was amazing. I got a turkey sandwich and it wasn't bad---not great but not bad. The internet was my biggest problem. This was a work trip and I REALLY needed the internet to meet a deadline but it didn't work for 80% of the trip. Very disappointing.

I tried to check in beforehand from Ireland. The Jet Blue website sent me to the Aer Lingus website and vice versa. I tried to get a boarding pass at Dublin Airport as well, but they said they couldn't help me either. I had to wait until I arrived at the gate in Boston to secure a boarding pass...it was a bit nerve wracking.

Great flight. Best in years. Very clean craft. Easy boarding. Communicative pilot. Friendly flight attendants. Absolutely smooth take off, in flight and landing. Very comfortable seats. Smoothest flight I've experienced in years. THANK YOU JET BLUE!

I was asked to pony up an additional $239 (over the $735 paid originally) for a one way middle seat, which was very uncomfortable. Where did you expect me to sit?

Jet Blue sevice was good. Just don't understand why they charge for earphones to listen to flight entertainment. Other than that, everything was excellent.

Mostly good, flight take off in time and land earlier I can’t ask for more..

The crew was not nice this time. I asked for a drink one time and the girl didn’t say anything to me and just got me the hot drink while walking super fast to the back. We were sitting in the back and she wasn’t doing anything except socializing. She was upset I asked for something and she had to do her job. I also didn’t fully have it in my hands when she handed it to me so it was dangerous. She was abrupt and rude. She wouldn’t allow for people to spread out like previous flights we had been on if they were empty, and there were empty rows. It was strange and she enjoyed being angry at us.

The plane was FREEZING COLD. Like I was wishing I'd brought gloves. Is this how JetBlue sells more blankets? Other than that, all fine. Crew just as nice as usual. A flight attendant asked (who? The pilot?) to have the air turned down for a great number of passengers who were as cold as I was. They (again -- who is "they") did not.

Flight was fine, but I was annoyed to have to pay for luggage again. We had paid for our luggage on our first two connecting flights with SATA Azores Airlines, but had to pay for luggage again with JetBlue at JFK airport. For one trip we paid over $500 for two suitcases to travel from Azores to San Francisco.

Everything was great the only issue was lack of Wi-Fi

The flight was delayed several times as they didn't have pilots. Then we were boarded on the plane and again waited on the tarmac for over 30-40 minutes waiting for pilots to board. The in flight entertainment was confusing at best on how to use it. It took multiple attempts to get wifi to connect and by the time it worked the flight was almost over.

The flight was delayed and gate changed so that was not fun and the flight to Dallas from LAX was very delayed on Sunday. It was just not a great experience due to the delays both ways.

Fine. No announcement for Concierge Key to board. Not a big issue just pointing it out.

Totally uninformed of the situation. Not yet sure about compensation. Highly disappointed.

Horrible. Their delay cause me to miss my connection, the the flight they rebooked was delayed over an hour because they over booked the crew. They also left my suitcase out in the rain for hours ruining items I had in the suitcase and blew off my complaint.. worst experience ever.

The flight was almost an hour delayed causing me to miss my connecting flight, then the rebooked flight was delayed a couple of hours. They also left my suitcase in the rain for hours ruining some items I had in there. They also just blew off my complaint. It was my absolute worst flight experience of all time:

Nothing available at the assigned hotel as far as brush, toothbrush, etc after forced layover with bags that departed

Crew tried to accommodate late arrival due to late departure

I will never but. through kayak again. and American Airlines. I will never fly again on. They're both thieves.

Waiting for gate in RDU for more than 20mins is crazy.

More options for your flight to Caribbean Islands

Complete your trip to Caribbean Islands with a hotel stay or car rental