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$151+ 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 1/17. Fares are subject to change and may not be available on all flights or dates of travel.
DAY — SJU
Jan 22 — Jan 291
Thu 1/22
Thu 1/29
1 adult, Economy
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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 December 23, 2025.

This American Airlines deal was found by Cheapflights users on 12/21. 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 12/241:56 pmDAY - SJU
1 stop7h 09mAmerican Airlines
Fri 12/266:00 amSJU - DAY
1 stop11h 46mAmerican Airlines
Deal found 12/21$399
This United Airlines deal was found by Cheapflights users on 12/21. 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.
Wed 12/245:21 pmDAY - SJU
2 stops11h 50mUnited Airlines
Fri 12/267:45 amSJU - DAY
2 stops13h 37mUnited Airlines
Deal found 12/21$489
This American Airlines deal was found by Cheapflights users on 12/21. 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 12/221:56 pmDAY - SJU
2 stops9h 03mAmerican Airlines
Tue 12/2310:25 amSJU - DAY
2 stops12h 17mAmerican Airlines
Deal found 12/21$494
This American Airlines deal was found by Cheapflights users on 12/21. 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 12/226:01 amDAY - SJU
1 stop16h 58mAmerican Airlines
Mon 12/296:00 amSJU - DAY
1 stop11h 43mAmerican Airlines
Deal found 12/21$599
This American Airlines deal was found by Cheapflights users on 12/21. 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.
Sun 12/286:00 amDAY - SJU
1 stop12h 43mAmerican Airlines
Wed 12/3110:25 amSJU - DAY
2 stops10h 28mAmerican Airlines
Deal found 12/21$609
This United Airlines deal was found by Cheapflights users on 12/21. 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.
Wed 12/245:21 pmDAY - SJU
2 stops11h 50mUnited Airlines
Thu 1/17:45 amSJU - DAY
2 stops13h 37mUnited Airlines
Deal found 12/21$662
This American Airlines deal was found by Cheapflights users on 12/22. 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 12/296:00 amDAY - SJU
1 stop16h 59mAmerican Airlines
Sat 1/36:00 amSJU - DAY
1 stop7h 37mAmerican Airlines
Deal found 12/22$710
This American Airlines deal was found by Cheapflights users on 12/22. 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.
Fri 12/261:57 pmDAY - SJU
1 stop8h 25mAmerican Airlines
Tue 12/306:00 amSJU - DAY
1 stop7h 37mAmerican Airlines
Deal found 12/22$722
This Delta deal was found by Cheapflights users on 12/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/256:05 amDAY - STT
1 stop8h 00mDelta
Tue 12/301:48 pmSTT - DAY
1 stop11h 11mDelta
Deal found 12/22$781
This American Airlines deal was found by Cheapflights users on 12/22. 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 12/276:59 amDAY - SJU
1 stop14h 06mAmerican Airlines
Sat 1/36:00 amSJU - DAY
1 stop7h 37mAmerican Airlines
Deal found 12/22$820
This United Airlines deal was found by Cheapflights users on 12/21. 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.
Mon 12/227:50 pmDAY - STT
1 stop17h 06mUnited Airlines
Mon 12/295:20 pmSTT - DAY
1 stop17h 43mUnited Airlines
Deal found 12/21$826
This United Airlines deal was found by Cheapflights users on 12/22. 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.
Thu 12/256:28 amDAY - STT
2 stops10h 14mUnited Airlines
Tue 12/303:05 pmSTT - DAY
2 stops29h 00mUnited Airlines
Deal found 12/22$832

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 December 23, 2025.

Round-trip from

$235
(United Airlines)

One-way from

$151
(American Airlines)

Popular in

August

Cheapest in

October

Average price

$577
From Dayton to Caribbean
Search Deals
One-way flight from Dayton to Caribbean
Search Deals
Highest demand for flights based on searches. 17% potential increase in price ($122 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($20 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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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 December 23, 2025.
Use the filters below to find and compare flights from Dayton to Caribbean that are best for you.

Fly from

Dayton

Fly to

Caribbean

Route

Depart

Return

Price

DaytonSan Juan

DAY - SJU

DAYSJU

Dayton

Thu 2/5

6:00 am-11:56 pm

1 stop16h 56m

San Juan Luis Munoz Marin Intl

Tue 2/10

7:07 am-2:55 pm

1 stop8h 48m

$268

DaytonSan Juan

DAY - SJU

DAYSJU

Dayton

Wed 1/21

2:37 pm-11:45 pm

1 stop8h 08m

San Juan Luis Munoz Marin Intl

Thu 1/29

7:30 am-1:48 pm

1 stop7h 18m

$280

DaytonSan Juan

DAY - SJU

DAYSJU

Dayton

Tue 1/20

10:24 am-10:22 pm

2 stops10h 58m

San Juan Luis Munoz Marin Intl

Wed 1/28

4:52 pm-11:44 pm

1 stop7h 52m

$325

DaytonSan Juan

DAY - SJU

DAYSJU

Dayton

Mon 1/19

2:52 pm-10:22 pm

1 stop6h 30m

San Juan Luis Munoz Marin Intl

Tue 1/27

7:45 am-10:02 pm

2 stops15h 17m

$325

DaytonSan Juan

DAY - SJU

DAYSJU

Dayton

Sun 1/18

10:24 am-10:22 pm

2 stops10h 58m

San Juan Luis Munoz Marin Intl

Tue 1/27

7:45 am-8:22 pm

2 stops13h 37m

$325

DaytonSan Juan

DAY - SJU

DAYSJU

Dayton

Sun 1/18

2:52 pm-10:22 pm

1 stop6h 30m

San Juan Luis Munoz Marin Intl

Thu 1/22

2:05 am-5:04 pm

2 stops15h 59m

$325

DaytonSan Juan

DAY - SJU

DAYSJU

Dayton

Sun 1/18

7:00 am-9:26 pm

2 stops13h 26m

San Juan Luis Munoz Marin Intl

Fri 1/30

4:52 pm-11:44 pm

1 stop7h 52m

$325

DaytonSan Juan

DAY - SJU

DAYSJU

Dayton

Sat 1/17

2:04 pm-6:11 am

2 stops15h 07m

San Juan Luis Munoz Marin Intl

Thu 1/22

2:05 am-5:04 pm

2 stops15h 59m

$325

DaytonSan Juan

DAY - SJU

DAYSJU

Dayton

Sat 2/7

2:04 pm-6:11 am

2 stops15h 07m

San Juan Luis Munoz Marin Intl

Tue 2/10

2:05 am-1:23 pm

2 stops12h 18m

$325

DaytonSan Juan

DAY - SJU

DAYSJU

Dayton

Sun 1/18

9:05 am-10:22 pm

2 stops12h 17m

San Juan Luis Munoz Marin Intl

Thu 1/22

8:10 am-2:17 pm

1 stop7h 07m

$325

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/20

Showing 1-10 of 40 results
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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, January is the cheapest month in which you can book a flight from Dayton to Caribbean (average of $128). Flying from Dayton to Caribbean in June is currently the most expensive (average of $230). 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.

What is the cheapest time of day to fly from DAY to CB?

Find hourly flight availability from Dayton to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 23, 2025.

It’s typically best to fly out from Dayton to Caribbean in the afternoon. Doing so could potentially save you 23% on the flight price compared to flying in the morning, which is usually more expensive.

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 December 23, 2025.
See what other customers who have flown with Delta, United Airlines, and American 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.
Delta
7.9
Good
8,014 reviews

Entertainment

7.9

Crew

8.5

Overall

7.9

Food

7.3

Boarding

8.1

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,014 reviews
Delta
7.9
Good
8,014 reviews

Entertainment

7.9

Crew

8.5

Overall

7.9

Food

7.3

Boarding

8.1

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,105 reviews
Delta
7.9
Good
8,014 reviews

Entertainment

7.9

Crew

8.5

Overall

7.9

Food

7.3

Boarding

8.1

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,054 reviews
Delta
7.9
Good
8,014 reviews

Entertainment

7.9

Crew

8.5

Overall

7.9

Food

7.3

Boarding

8.1

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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 8h 08m. Fly via American Airlines, Delta, or United Airlines to get the fastest option. There are 1837 mi between Dayton and Caribbean. This flight may include one or multiple stops.

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

    While some choose either Dayton - Oranjestad Reina Beatrix or Dayton - Saint Thomas Island Cyril E King, Dayton - San Juan Luis Munoz Marin Intl is the most popular route 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, January is the cheapest month in which you can book a flight from Dayton to Caribbean (average of $128). Flying from Dayton to Caribbean in June is currently the most expensive (average of $230). 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

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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 December 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$264Average$701FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$305Average$639FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$370Average$729FlexibilityNo cancel feeOn-time71%

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