Caribbean

$123+ Cheap flights from Dayton (DAY) to Caribbean

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/2. Fares are subject to change and may not be available on all flights or dates of travel.
DAY — SJU
Jun 8 — Jun 151
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Cheap flight deals from Dayton to Caribbean

Cheapest flights from Dayton to Caribbean
Explore the most affordable flight options available from Dayton to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 9, 2026.

This American Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:48 am
DAY
-
SJU
1 stop17h 27m
American Airlines
Sat 8/2910:33 am
SJU
-
DAY
2 stops11h 15m
American Airlines
Deal found 5/4$326
This American Airlines deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/245:55 pm
DAY
-
SJU
1 stop5h 55m
American Airlines
Sat 10/313:50 pm
SJU
-
DAY
1 stop6h 10m
American Airlines
Deal found 5/8$327
This American Airlines deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/26:00 am
DAY
-
SJU
1 stop7h 43m
American Airlines
Wed 9/97:05 pm
SJU
-
DAY
2 stops15h 47m
American Airlines
Deal found 5/7$331
This American Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:55 pm
DAY
-
MBJ
2 stops18h 05m
American Airlines
Tue 10/275:00 pm
MBJ
-
DAY
2 stops19h 00m
American Airlines
Deal found 5/6$357
This American Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/215:55 pm
DAY
-
MBJ
2 stops18h 05m
American Airlines
Tue 10/2710:50 am
MBJ
-
DAY
1 stop7h 54m
American Airlines
Deal found 5/5$362
This American Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/105:32 pm
DAY
-
SJU
1 stop6h 27m
American Airlines
Tue 8/186:51 am
SJU
-
DAY
2 stops13h 18m
American Airlines
Deal found 5/5$366
This American Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/78:00 am
DAY
-
SJU
2 stops10h 05m
American Airlines
Wed 10/143:25 pm
SJU
-
DAY
1 stop8h 58m
American Airlines
Deal found 5/6$371
This Faresmojo deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/43:06 pm
DAY
-
SJU
1 stop7h 23m
JetBlue
Tue 8/116:48 am
SJU
-
DAY
1 stop7h 29m
JetBlue
Deal found 5/6$396
This United Airlines deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/249:00 am
DAY
-
SJU
2 stops14h 50m
United Airlines
Sat 10/317:30 am
SJU
-
DAY
1 stop6h 31m
United Airlines
Deal found 5/8$406
This American Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/125:49 am
DAY
-
SJU
1 stop17h 03m
American Airlines
Thu 12/176:25 am
SJU
-
DAY
1 stop15h 36m
American Airlines
Deal found 5/6$418
This American Airlines deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/215:50 am
DAY
-
SJU
1 stop17h 07m
American Airlines
Sun 7/267:14 pm
SJU
-
DAY
2 stops26h 11m
American Airlines
Deal found 5/7$420
This American Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/236:31 am
DAY
-
STT
1 stop7h 17m
American Airlines
Wed 7/294:50 pm
STT
-
DAY
2 stops19h 09m
American Airlines
Deal found 5/5$420

Find flight deals from Dayton to Caribbean

Keep the following information in mind while searching for Dayton to Caribbean flight deals. Data was last updated May 9, 2026.

Round-trip from

$326
(American Airlines)

One-way from

$123
(Delta)

Popular in

August

Cheapest in

October

Average price

$524
From Dayton to Caribbean
One-way flight from Dayton to Caribbean
Highest demand for flights based on searches. 4% potential increase in price ($25 potential increase over avg. RT price).
Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average RT price).
Average for round-trip flights in May 2026

Cheapflights Fare Finder

 
Customize your flight search to find flights from Dayton to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 9, 2026.
Use the filters below to find and compare flights from Dayton to Caribbean that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

DaytonSan Juan

DAY - SJU

DAYSJU

Dayton

Sat 8/22

6:48 am-12:15 am

1 stop17h 27m

San Juan Luis Munoz Marin Intl

Sat 8/29

10:33 am-9:48 pm

2 stops11h 15m

$326

DaytonMontego Bay

DAY - MBJ

DAYMBJ

Dayton

Thu 10/22

5:55 pm-11:00 am

2 stops18h 05m

Montego Bay Sangster Intl

Tue 10/27

5:00 pm-1:00 pm

2 stops19h 00m

$357

DaytonMontego Bay

DAY - MBJ

DAYMBJ

Dayton

Wed 10/21

5:55 pm-11:00 am

2 stops18h 05m

Montego Bay Sangster Intl

Tue 10/27

10:50 am-7:44 pm

1 stop7h 54m

$362

DaytonSan Juan

DAY - SJU

DAYSJU

Dayton

Fri 8/28

6:00 am-6:24 pm

2 stops12h 24m

San Juan Luis Munoz Marin Intl

Sat 9/5

10:33 am-9:48 pm

2 stops11h 15m

$366

DaytonSaint Thomas Island

DAY - STT

DAYSTT

Dayton

Thu 7/23

5:51 pm-12:59 pm

2 stops19h 08m

Saint Thomas Island Cyril E King

Wed 7/29

4:50 pm-11:59 am

2 stops19h 09m

$420

DaytonSan Juan

DAY - SJU

DAYSJU

Dayton

Tue 5/19

2:55 pm-9:24 pm

1 stop6h 29m

San Juan Luis Munoz Marin Intl

Sat 5/23

7:20 am-2:18 pm

1 stop6h 58m

$451

DaytonSan Juan

DAY - SJU

DAYSJU

Dayton

Sat 7/4

2:53 pm-9:24 pm

1 stop6h 31m

San Juan Luis Munoz Marin Intl

Wed 7/8

7:20 am-2:18 pm

1 stop6h 58m

$494

DaytonGeorge Town

DAY - GCM

DAYGCM

Dayton

Fri 7/3

5:51 pm-10:55 am

2 stops18h 04m

George Town Owen Roberts Intl

Wed 7/8

5:10 pm-11:59 am

2 stops17h 49m

$497

DaytonSan Juan

DAY - SJU

DAYSJU

Dayton

Mon 8/3

4:07 pm-11:48 pm

1 stop7h 41m

San Juan Luis Munoz Marin Intl

Wed 8/12

6:51 am-9:48 pm

1 stop14h 57m

$498
Quickest round-trip

DaytonNassau

DAY - NAS

DAYNAS

Dayton

Thu 8/27

6:00 am-11:51 am

1 stop5h 51m

Nassau Intl

Wed 9/2

1:13 pm-5:51 pm

1 stop4h 38m

$499

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/7

Showing 1-10 of 52 resultsSorted by cheapest first
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6

Best time to book a flight from Dayton to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean from Dayton with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Dayton to Caribbean

What is the cheapest month to book a flight from Dayton to Caribbean?

Currently, October is the cheapest month in which you can book a flight from Dayton to Caribbean (average of $118). Flying from Dayton to Caribbean in June is currently the most expensive (average of $447). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated May 9, 2026.
See what other customers who have flown with Delta,United Airlines, andAmerican Airlines from Dayton to Caribbean have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.

Comfort

7.9

Overall

7.9

Boarding

8.1

Food

7.2

Entertainment

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional

Comfort

7.9

Overall

7.9

Boarding

8.1

Food

7.2

Entertainment

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional

Comfort

7.9

Overall

7.9

Boarding

8.1

Food

7.2

Entertainment

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional

Comfort

7.9

Overall

7.9

Boarding

8.1

Food

7.2

Entertainment

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional

Related info for your journey

Find useful and relevant information for your journey from Dayton to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
  • What airport do you fly from for flights from Dayton to Caribbean?

    Most people fly from Dayton (DAY) if they book a flight from Dayton to Caribbean. Dayton is conveniently located just 10.0 mi from Dayton’s city center.

  • How long is the flight from Dayton to Caribbean?

    There are many flights that can get you from Dayton to Caribbean in 5h 51m. Fly via American Airlines, United Airlines, or Delta to get the fastest option. There are 1098 mi between Dayton and Caribbean. This flight may include one or multiple stops.

  • What are the most popular routes from Dayton to Caribbean?

  • Can I find deals for flights from Dayton to Caribbean that include hotel bookings?

    Yes. In addition to deals on Dayton to Caribbean flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Dayton to Caribbean?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Dayton to Caribbean.

  • Can I find deals for business class flights from Dayton to Caribbean?

    Yes. Cheapflights offers flight deals from Dayton to Caribbean by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Dayton to Caribbean?

    Currently, October is the cheapest month in which you can book a flight from Dayton to Caribbean (average of $118). Flying from Dayton to Caribbean in June is currently the most expensive (average of $447). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Dayton to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.

Top 3 airlines flying from Dayton to Caribbean

Discover the top 3 airlines that operate flights from Dayton to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 9, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$281Average$716FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$286Average$548FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$319Average$685FlexibilityNo cancel feeOn-time71%

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