$137 Find Cheap Flights from Omaha to Caribbean - Compare and Save

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Cheap Flights from Omaha to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Sort by: Cheapest
San Juan, Puerto Rico
6h 55m2 stops
from $375per person
Montego Bay, Jamaica
6h 29m2 stops
from $413per person
Saint Thomas Island, U.S. Virgin Islands
7h 18m2 stops
from $490per person
Providenciales, Turks and Caicos Islands
6h 25m2 stops
from $518per person
George Town, Cayman Islands
6h 25m2 stops
from $536per person
Simpson Bay, St. Maarten
7h 25m2 stops
from $555per person
Nassau, The Bahamas
5h 25m2 stops
from $558per person
Oranjestad, Aruba
7h 45m2 stops
from $605per person
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Booking Insights

KAYAK's insights & trends for Omaha to Caribbean flights

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

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

The cheapest month for flights from Omaha to Caribbean is April, when tickets cost $518 (return) on average. On the other hand, the most expensive months are June and December, when the average cost of round-trip tickets is $703 and $695 respectively.

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

To get a below average price on the flight from Omaha to Caribbean, 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

$137
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 19% increase in price.
Flight from Omaha to San Juan

FAQs - booking Caribbean flights

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

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

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

 
Need help choosing which airline to fly with from Omaha 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.
8.0
SouthwestOverall score based on 4196 reviews
7.0Food
8.0Comfort
8.1Boarding
8.6Crew
7.5Entertainment
Airline reviews

Flight was fine. Only thing was flight was delayed nearly 2 hours. Flight was originally scheduled to depart at 7:50pm but didn't depart until 9:50pm. I got home around midnight. It was later than desired and I had to get up early next day to take kids to practice. I have noticed that last flight of day on West Coast for Southwest always tend to have delays.

6.0 GoodAnonymous, Sep 2026
Read more Southwest reviews

Flight was fine. Only thing was flight was delayed nearly 2 hours. Flight was originally scheduled to depart at 7:50pm but didn't depart until 9:50pm. I got home around midnight. It was later than desired and I had to get up early next day to take kids to practice. I have noticed that last flight of day on West Coast for Southwest always tend to have delays.

Wasn't expecting this, but, we actually ended up getting assigned to the first row of seats!!!!! The extra legroom came in handy

Trash experience on all my flights this week. Delay after delay. The flight I’m waiting for has been delayed 6 times and nearly 3 hours.

Southwest has been a nightmare. Delayed flights, missed connections, systems down. Never again am I flying southwest.

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.

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.

Gate agents call groups one and two and give about 3-5 minutes for each group to board, then the call groups three and four together and it causes a bottleneck in the line. Give each group 3-5 minutes to board before calling the next group.

We sat at the gate for over 30 minutes, with no indication as to why

I didn't really interact with any of the crew since we had a bumpy ride and no refreshments were distributed.

It was delayed over an hour and a lot of announcements disrupting movie.

My flight experience was generally good, but the boarding process was stressful. I was pulled out of line at the gate during the photo ID check, and after being cleared, I was never given an explanation for the delay despite asking for clarification. This lack of communication was the only downside to an otherwise smooth trip.

I didn't use the onboard amenities, so it is difficult to comment on those services. Otherwise, the flight from Nashville to Toronto was quite crowded, but the boarding process and the flight itself were perfectly fine.

Seats were old and very uncomfortable. Coach seating is way too tight

WiFi was a major problem and if it does not work on a 4 hour flight then that lowers the overall experience

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.

Smooth flight, easy boarding process. Made up time in the air with initial delay due to weather pass through

Flight was over two hours late, but they notified us early in the morning. They ended up changing planes the food on board that was extremely mediocre and we were in premier class.

Usual wait for over a half hour for a gate at Ohare. They tell you you'll get there early then sit on the plane and wait almost an hour

I enjoyed it, again I believe air Canada has better seating options and better drink options

Plane congestion resulted in a 1 hr wait from landing to arrival at the gate. This was in addition to also experiencing extreme delays on my incoming flight.

Delayed too much. 1.5 hrs in the airport and another 1 hr in the runway. Got too late in the night. There was no proper food available.

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.

Thought the economy premium experience would match that of the Amsterdam to Boston flight. Aircraft was older: chair didn’t lean back. I had to buy a blanket, which on the flight over was complimentary. Flight crew seemed disinterested all around.

I propose enhancing the legroom across the entire cabin seating area and expanding the snack selection. The airline companies should prioritize customer needs over the extravagant and unjustified salaries of upper management.

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!

The crew was wonderful, the plane was fine. We left the gate on time, but we had to wait 40 minutes on the tarmac because of all the congestion at Boston.

Seats were the worst i ever experienced — narrow, hard, no leg room and a long flight

ontime. Seats are terribly close together for someone my height.

I don’t think I’ve ever had a flight with American that has been without problems. Mostly delays - this time for over 3 hours. They should have just brought another plane into the terminal but they just had everyone sitting around misterable all day. They turned a 3 hour flight into a 12 hour trip for me (including the “planned” layover). It was ridiculous.

The flight from American side was good, my main issue this was a part of a partner flight with gol, preventing me to use digital boarding passes and doing checking previous of the arrival to the airport.

Id like for them to not have lost my bag. And maybe be a little nicer to me, given the fact they lost my bag.

The flight was delayed but we were given no updates. The time just kept changing in the board. We were delayed on the runway as well. Then, my bag was lost and still hasn't been returned.

The flight landed in Phoenix and taxied the runway for 15 additional minutes. I had a connecting flight I barely made it to because of the delay of the plane taxing the runway.

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

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