$163 Find Cheap Flights from Omaha to Caribbean

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Omaha to Caribbean departing on 8/22. 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 Omaha to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana2 stops$588
Santo Domingo
Santo Domingo1 stop$630
Montego Bay
Montego Bay1 stop$352
Oranjestad
Oranjestad2 stops$666
Nassau
Nassau1 stop$566
Simpson Bay
Simpson Bay1 stop$565
Providenciales
Providenciales2 stops$518
Bridgetown
Bridgetown2 stops$697
George Town
George Town2 stops$504
Willemstad
Willemstad1 stop$714
Puerto Plata
Puerto Plata2 stops$809
St. John's
St. John's2 stops$735
Punta Cana
Punta Cana2 stops$588
Santo Domingo
Santo Domingo1 stop$630
Montego Bay
Montego Bay1 stop$352
Oranjestad
Oranjestad2 stops$666
Nassau
Nassau1 stop$566
Simpson Bay
Simpson Bay1 stop$565
Providenciales
Providenciales2 stops$518
Bridgetown
Bridgetown2 stops$697
George Town
George Town2 stops$504
Willemstad
Willemstad1 stop$714
Puerto Plata
Puerto Plata2 stops$809
St. John's
St. John's2 stops$735

Book Cheap Omaha 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 Omaha 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 Omaha to Caribbean

seg, ago 17 - qua, ago 26
Delta Logo
1:41 pm - 10:29 pm
OMA
-
SJU
7h 48m
1 stop
Delta Logo
2:59 pm - 11:59 pm
SJU
-
OMA
10h 00m
1 stop
$326Delta
qua, out 21 - qua, out 28
American Airlines Logo
1:58 pm - 11:50 pm
OMA
-
SJU
8h 52m
1 stop
American Airlines Logo
8:35 am - 6:24 pm
SJU
-
OMA
10h 49m
2 stops
$331American Airlines
sáb, out 17 - qua, out 28
United Airlines Logo
6:00 am - 8:38 pm
OMA
-
SJU
13h 38m
2 stops
United Airlines Logo
7:30 am - 5:21 pm
SJU
-
OMA
10h 51m
2 stops
$340United Airlines
sáb, out 17 - qua, out 28
United Airlines Logo
6:00 am - 8:38 pm
OMA
-
SJU
13h 38m
2 stops
United Airlines Logo
7:30 am - 5:21 pm
SJU
-
OMA
10h 51m
2 stops
$341United Airlines
sáb, out 24 - sex, out 30
United Airlines Logo
6:00 am - 3:45 pm
OMA
-
MBJ
9h 45m
1 stop
United Airlines Logo
2:36 pm - 10:33 am
MBJ
-
OMA
19h 57m
2 stops
$352United Airlines
seg, set 14 - sáb, set 19
American Airlines Logo
6:26 pm - 11:01 am
OMA
-
MBJ
16h 35m
2 stops
American Airlines Logo
5:16 pm - 1:15 pm
MBJ
-
OMA
19h 59m
2 stops
$357American Airlines
qua, ago 26 - ter, set 1
Southwest Logo
10:35 am - 9:05 pm
OMA
-
SJU
9h 30m
2 stops
Southwest Logo
1:20 pm - 9:45 pm
SJU
-
OMA
9h 25m
2 stops
$376Southwest
seg, nov 2 - sex, nov 6
Southwest Logo
10:25 am - 10:55 pm
OMA
-
SJU
10h 30m
2 stops
Southwest Logo
5:35 am - 3:45 pm
SJU
-
OMA
12h 10m
2 stops
$379Southwest
sex, ago 21 - ter, ago 25
Delta Logo
5:30 am - 4:38 pm
OMA
-
SJU
10h 08m
1 stop
Delta Logo
7:00 am - 5:20 pm
SJU
-
OMA
11h 20m
1 stop
$381Delta
sex, nov 6 - seg, nov 9
Air Canada Logo
1:45 pm - 2:35 pm
OMA
-
BGI
22h 50m
2 stops
Air Canada Logo
4:50 pm - 5:21 pm
BGI
-
OMA
26h 31m
2 stops
$1,301Air Canada
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?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Omaha 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 Omaha to Caribbean is January, when tickets cost $108 (return) on average. On the other hand, the most expensive months are November and July, when the average cost of round-trip tickets is $235 and $233 respectively.

How far in advance should I book a flight from Omaha 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 Omaha 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 Omaha to Caribbean, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 7 weeks before departure.

Good to know

Low seasonAugust
Cheapest flight$163
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly and prices are also 5% lower on average.
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 4262 reviews
8.1Boarding
8.6Crew
7.5Entertainment
7.0Food
8.0Comfort
Airline reviews

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.

4.0 OkayAnonymous, May 2026
MDW - LAX
Read more Southwest reviews

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.

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.

The crew were efficient. The pilots seemed professional. It was a bit chilly in our seats. The sheet provided weren’t very helpful.

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

The Boarding process was great. Particularly since my wife and I require assistance. The flight attendants were amazing. We travel frequently; they honestly were a cut above. 😀

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

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.

I felt scammed. The priced advertised was different than what I paid. I paid the whole some online. I then got a call 20 minutes later saying I need to paid 70 more person. She said the price online is not the guaranteed price.

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

Easy of boarding, helpfully staff at check in, surprisingly comfortable seating

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.

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.

Lost of requested seat assignments. Lost my husband's meal choice

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

It was fine for what it was. It’s not luxury travel but it was efficient, for the most part. Having my carry-on transferred into luggage however, was unwelcome.

We had better-than-average leg room and I loved the access to shows and movies. During boarding, we could not hear the agent even though we were close to the boarding door, which was kind of scary when we realized that half of the passengers had already boarded. Also, the entertainment was awesome, but I could not hear the movie as well as I would have liked, because my headphones were crappy. It would have been better if I could connect my own ear buds via Bluetooth or if JetBlue provided headphones.

On time, friendly attendants, quick wheelchair assistance and help checking in bags. Also appreciated change in seats, more forward to make it easier for my 97 year old mother to board and exit the plane. Thank you, JetBlue!

Flight did not have onboard charging and TV screen flickering.

I was seated next to an autistic child who was out of control and had a child behind me kicking my seat for most of the trip. I will never fly JetBlue again. Ever. I don't care how cheap it is. It's terrible.

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

This was the first flight I've taken since pre-pandemic. I was pleased with how orderly the boarding and disembarking went. The seats were comfortable. I loved that there was no "first class'. The attendants and passengers I met were all very friendly and welcoming.

Boarding was easy. Provided drinks and snacks. Good aircraft and staff

Not very happy because of the long delaying which causes our luggages were not on the connection flight and nearly missed our connection flight.

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.

B-class on an old plane with antiquated amenities and poor service. Landed in Rome w/o bag that didn’t make the connection (plenty of time in London). Bag will come to hotel NOT the day it lands but the following night!! Still waiting for bag…BA had nothing to offer in support and couldn’t even tell me their comp, told to submit receipts and then I’ll learn what is or isn’t covered.

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.

The flight attendants were very friendly, efficient, and helpful. The plane was ahead of schedule, and it all went very smoothly. Thank you.

They lost my baggage and I am still struggling to the information and update

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports