$161 Find Cheap Flights from Omaha to Caribbean Islands - Compare and Save

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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$556
Santo Domingo
Santo Domingo2 stops$642
Montego Bay
Montego Bay2 stops$357
Oranjestad
Oranjestad2 stops$437
Nassau
Nassau2 stops$482
Providenciales
Providenciales1 stop$465
Bridgetown
Bridgetown2 stops$775
George Town
George Town2 stops$407
Willemstad
Willemstad2 stops$613
St. John's
St. John's2 stops$817
Puerto Plata
Puerto Plata2 stops$815
Punta Cana
Punta Cana1 stop$556
Santo Domingo
Santo Domingo2 stops$642
Montego Bay
Montego Bay2 stops$357
Oranjestad
Oranjestad2 stops$437
Nassau
Nassau2 stops$482
Providenciales
Providenciales1 stop$465
Bridgetown
Bridgetown2 stops$775
George Town
George Town2 stops$407
Willemstad
Willemstad2 stops$613
St. John's
St. John's2 stops$817
Puerto Plata
Puerto Plata2 stops$815
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 $381, 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 $572 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $744 and $736 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

Cheapest flight

$161
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly and prices are also 1% lower on average.
Flight from Omaha to San Juan

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 4188 reviews
8.6Crew
8.1Boarding
7.0Food
8.0Comfort
7.5Entertainment
Airline reviews

had to check bag at gate when there was still overhead bin space. As usual the WIFI didn't really work.

6.0 GoodAnonymous, Sep 2026
Read more Southwest reviews

had to check bag at gate when there was still overhead bin space. As usual the WIFI didn't really work.

Terrible delay today. also, waited 90 minutes for baggage to unload in Seattle earlier in the week.

Like new plane. Great crew. Comfortable. Clean. On time. Happy employees. Good organization and control of passengers.

Flights delays were communicated timely and helpfully, but there was a significant delay without any real effort to make up for that. Also, the in-flight WiFi was very spotty. That said, this was my first time with Southwest and I was quite happy with the service and staff otherwise.

Delayed and once landed waited very long for the luggage

Nice managed … it was a smaller plane, so the seating wasn’t as comfortable.

The Southwest airline was ok. A big thank you to Kayak team (David), who worked with me on Sunday afternoon to rebook my travel from Burbank, CA, to CVG. My original flight on Sunday was delayed, so I had to cancel Sunday flight and rebook my travel to Monday. Could not have done it without help from David from Kayak team. Ante Soda GE Aerospace

Seated at front bulkhead for a smidge extra leg room away from home and on flight back home. Away crew was very proactive about assuring our carryons had space close behind us (because no seat in front of us our personal items had to be in a small bin overhead). They actively required passengers place overhead luggage on its side so more items could fit in bins. Home crew made no such efforts. I had to struggle back rows to get overhead bags upon landing, no crew help then either, and some disgruntled passengers as I and others retrieved our bags. There was a system that worked pretty well. The home bound crew just didn't feel like working.

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.

For some reason, there was very little volume on the cabin announcements. You could not hear what the pilot or crew were saying.

Carmen was an absolute delight on the flight staff! Everyone was lovely and made it a very pleasant flight.

Flight was delayed at airport with large backlog and WiFi was spotty

I don’t like mushrooms and that’s all they had with pasta

I Love Delta but one of the flight crew training in courtesy snd hospitality.

I don't know why the crew decided to board 15 minutes early without informing anyone not at the gate. Why would you have the app send a notification that we're boarding on time, instead board early, and then rush me to the gate. Then have me check my carry-on when I specifically packed my bag as to not do so.

Could have been on time and not missed my connection

Really hard to tell what was happening after my flight got delayed five times

Flight was delayed from San Diego due to being overweight for weather conditions. We missed our connecting flight to our final destination due to the delay, as well as the connecting flight leaving before the scheduled departure time. We missed the connection within 10 - 15 minutes. We were booked on a later flight arriving 7 hours later. There were 7 passengers sharing the same originating and connecting flight.

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

Very disappointing that on an international business class flight they would not give me access to the lounge in Boston. They said it was because it was a codeshare flight. International business class should include lounge access regardless of codeshare.

They did not have free WIFI and I was not okay with that!

Food was very bad Crew was not so welcoming. Chairs was so uncomfortable

Flight was on time, clean, etc. Despite connecting to your wi fi I was unable to use your app to watch entertainment.

I initially boarded in a very comfortable and large plane and was told there was a mechanical issue with a waste receptacle. We sat on the plan for a good few hours, then were told we can deplane and that we would take off shortly. Delays continued and four hours later my flight was cancelled, and I had to quickly rebook another. The flight I rebooked was also delayed, and I when we boarded, I wound up on a small plane in a middle seat for the 6-hour journey and it was extremely uncomfortable. No issues with the staff in any way, just the overall experience of the delays, cancellations, and downgrade in comfort on such a long flight. It is significantly impactful on how you feel post travel and I was exhausted and sore from the experience.

Awful!!!. I do not recommend United. The flight staff are unhappy and don't attempt to make the passengers feel comfortable or welcome. The food is not edible, and the seats are miserable. My expensive luggage was destroyed, and the ticket prices are too much for the experience.

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.

Had to pay for WiFi, delayed start, and sat on the runway forever.

As with most flights these days it was delayed by about 30 min.

The airline company should manage their crew for the plane on better schedule so people don’t have to wait in the plane. And this flight that I had had no snacks offered, and if you would like a water, you had to come see somebody and ask for. If airline would let people know that they are no longer providing or offering any food. At least people could bring their own if they wish.

The flight was delay roughly 90 minutes. Once we arrived at O'Hare, we sat on the tarmac for another 90 minutes. I understand that O'Hare is under construction however they need to figure out a solution as every incoming flight I have been on has been delayed coming to a gate.

The WiFi was out gr entire flight. Had to Diane for almost 1 hour to wait for a gate to open up for plane to dock. Very bad experience.

It was a short flight so there were no entertainments nor super comfortable which is OKAY, just the review system doesnt allow for N/A which is why okay was put, but overall good! No delays and nice crew

We were stuck with no gate upon landing for 90 minutes. Unacceptable.

It was significantly delayed. Also the admirals club in Philadelphia airport near Gate B is absolutely filthy. Good was on the floor. Flies on the cheese. And the men’s restroom had pools of urine on the floor. I am not using that lounge again.

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.

KUDOS TO ALL THE CREW PROVIDING ASSISTANCE WITH PASSENGERS ON A WHEELCHAIR. ON BOTH FLIGHTS THEY HUSTLED TO TAKE MY RELATIVE TO CONNECTION ON TIME. THEY DESERVE A LOT OF CREDIT!

Good experience with this flight. Boarding was smooth with no issues. The short flight was good with quick drink & snack service. Nice easy way to get back from DC.

Very good flight that left on time and arrived earlier than anticipated, which was a plus! The crew members were very welcoming and helpful. However, the temperature on the flight was very cold - almost to the point of extreme discomfort. Additionally, requiring passengers to pay $8 for headphones to access the JetBlue entertainment was disappointing. Those earbud jacks are not used with most technology and would not be able to be used. There was no option to use Bluetooth for my own earbuds. Beyond those inconveniences, the flight was good.

My original flight was cancelled. My replacement flight was delayed over 2 hours. I lost my whole day in NY

Delays were crazy long (over an hour) both for boarding and baggage claim

awful expereince. boarding was a mess and not communicated, then we sat on a hot plane and were at risk of getting kicked off

2 hour delay and a lack of air conditioning on the plane. Not a good combination

Fabulous! This was the first time we've flown with JetBlue and the entire experience was flawless!

First time flying JetBlue and my perception changed. Love it.

Poor, had a 5+ hours delay. Kept sitting in the aircraft with three kids. It was terrible

More options for your flight to Caribbean Islands

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